Name: 615-42-9|1,2-Diiodobenzene|98% (stabilized with Copper chip)
Brand: Ambeed
SKU: A191924
Price: 5.0 USD
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1
[ 591-50-4 ]
[ 615-42-9 ]
[ 83846-48-4 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1988,vol. 24,p. 2029 - 2035
Zhurnal Organicheskoi Khimii,1988,vol. 24,p. 2251 - 2258
[2]Journal of Organic Chemistry USSR (English Translation),1988,vol. 24,p. 2029 - 2035
Zhurnal Organicheskoi Khimii,1988,vol. 24,p. 2251 - 2258

2
[ 615-42-9 ]
[ 201230-82-2 ]
[ 106-49-0 ]
[ 2142-03-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained
80%	With 1,4-diaza-bicyclo[2.2.2]octane; palladium 10% on activated carbon In toluene at 120℃; for 2h; Autoclave;
70%	With bis(triphenylphosphine)palladium(II)-chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl acetamide at 115℃; for 1h;

Reference： [1]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]
[2]Khedkar, Mayur V.; Khan, Shoeb R.; Sawant, Dinesh N.; Bagal, Dattatraya B.; Bhanage, Bhalchandra M. [Advanced Synthesis and Catalysis, 2011, vol. 353, # 18, p. 3415 - 3422]
[3]Perry, Robert J.; Turner, S. Richard [Journal of Organic Chemistry, 1991, vol. 56, # 23, p. 6573 - 6579]

3
[ 615-42-9 ]
[ 201230-82-2 ]
[ 106-47-8 ]
[ 7386-21-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained
60%	With bis(triphenylphosphine)palladium(II)-chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl acetamide at 115℃; for 4.3h;

Reference： [1]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]
[2]Perry, Robert J.; Turner, S. Richard [Journal of Organic Chemistry, 1991, vol. 56, # 23, p. 6573 - 6579]

4
[ 615-42-9 ]
[ 201230-82-2 ]
[ 99-92-3 ]
[ 40101-59-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1,4-diaza-bicyclo[2.2.2]octane; palladium 10% on activated carbon In toluene at 120℃; for 2h; Autoclave;
55%	With bis(triphenylphosphine)palladium(II)-chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl acetamide at 115℃; for 4.6h;
46%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained

Reference： [1]Khedkar, Mayur V.; Khan, Shoeb R.; Sawant, Dinesh N.; Bagal, Dattatraya B.; Bhanage, Bhalchandra M. [Advanced Synthesis and Catalysis, 2011, vol. 353, # 18, p. 3415 - 3422]
[2]Perry, Robert J.; Turner, S. Richard [Journal of Organic Chemistry, 1991, vol. 56, # 23, p. 6573 - 6579]
[3]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]

5
[ 615-42-9 ]
[ 201230-82-2 ]
[ 104-94-9 ]
[ 2142-04-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; under 760.051 Torr; for 4h;Schlenk technique;	General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained

Reference： [1]Advanced Synthesis and Catalysis,2011,vol. 353,p. 3415 - 3422
[2]Applied Catalysis A: General,2018,vol. 560,p. 73 - 83
[3]Journal of Organic Chemistry,1991,vol. 56,p. 6573 - 6579
[4]Advanced Synthesis and Catalysis,2016,vol. 358,p. 314 - 320

6
[ 615-42-9 ]
[ 201230-82-2 ]
[ 62-53-3 ]
[ 520-03-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With 1,4-diaza-bicyclo[2.2.2]octane; palladium 10% on activated carbon In toluene at 120℃; for 2h; Autoclave;
91%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained
89%	With triethylamine In toluene at 100℃; for 6h; Autoclave;	General procedure carbonylative cyclization ofmethyl-2-iodobenoate/1,2-diiodo benzene for the synthesis ofN-substituted isoindole-1,3-diones using ImmPd-IL as a catalyst General procedure: General procedure carbonylative cyclization ofmethyl-2-iodobenoate/1,2-diiodo benzene for the synthesis ofN-substituted isoindole-1,3-diones using ImmPd-IL as a catalystIn a 100 mL stainless steel autoclave, methyl-2-iodobenoate/1,2-diiodobenzene (1 mmol), aryl amine (2 mmol), ImmPd-IL(2 mol%), toluene (10 mL) and Et3N (2.5 mmol) were added. Theautoclave was closed, purged three times with nitrogen followedwith carbon monoxide, and then pressurized with 1 atm of CO andheated at 100C for 6 h. After completion of reaction the reac-tor was cooled to room temperature, the remaining CO gas wascarefully vented, and the reactor was opened. The reactor vesselwas thoroughly washed with ethyl acetate (10-15 mL) to removeany traces of product and catalyst if present. The catalyst was fil-tered and the reaction mixture was evaporated under vacuum. Theresidue obtained was purified by column chromatography (silicagel, 60-120 mesh; petroleum ether/ethyl acetate, 95:05) to affordthe desired product. The products were confirmed by GC, GC-MS,1H NMR and13C NMR spectroscopic techniques. The purity of com-pounds was determined by GC-MS analysis.

63%	With bis(triphenylphosphine)palladium(II)-chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl acetamide at 115℃; for 1.5h;
63%	With bis(triphenylphosphine)palladium(II)-chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl acetamide at 115℃; for 1.5h; other catalyst, other solvent, other base, variations of temperature and pressure; other arylamines;

Reference： [1]Khedkar, Mayur V.; Khan, Shoeb R.; Sawant, Dinesh N.; Bagal, Dattatraya B.; Bhanage, Bhalchandra M. [Advanced Synthesis and Catalysis, 2011, vol. 353, # 18, p. 3415 - 3422]
[2]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]
[3]Khedkar, Mayur V.; Shinde, Ajinkya R.; Sasaki, Takehiko; Bhanage, Bhalchandra M. [Journal of Molecular Catalysis A: Chemical, 2014, vol. 385, p. 91 - 97]
[4]Perry, Robert J.; Turner, S. Richard [Journal of Organic Chemistry, 1991, vol. 56, # 23, p. 6573 - 6579]
[5]Perry, Robert J.; Turner, S. Richard [Journal of Organic Chemistry, 1991, vol. 56, # 23, p. 6573 - 6579]

7
[ 615-42-9 ]
[ 91-60-1 ]
[ 205-43-6 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2593 - 2598

8
[ 615-42-9 ]
[ 1066-54-2 ]
[ 73392-23-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine for 4h; Heating;
97%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 16h;
96%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;

96%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 48h; Darkness; Inert atmosphere; regioselective reaction;
95%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine at 110℃; for 0.25h; Inert atmosphere; Sealed tube; Microwave irradiation;
94%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In tetrahydrofuran at 60℃; for 20h; Inert atmosphere;
90%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine at 25℃; for 20h; Inert atmosphere;
86%	Stage #1: 1,2-Diiodobenzene With copper(l) iodide; triethylamine at 60℃; for 0.5h; Inert atmosphere; Stage #2: trimethylsilylacetylene With bis-triphenylphosphine-palladium(II) chloride at 20℃; for 48h; Inert atmosphere;
85%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In various solvent(s) at 60℃;
84%	With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;
81%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In benzene at 20℃; for 13h; Inert atmosphere;	1,2-Bis(trimethylsilylethynyl)benzene (7)[2] A mixture of 1,2-diiodobenzene (3.0 g, 9.1 mmol), trimethylsilylacethylene (2.7 g, 27 mmol),Et3N (3.0 g, 30 mmol), CuI (173 mg, 0.9 mmol), and Pd(PPh3)2Cl2 in degassed benzene wasstirred for 13h under Ar atmosphere at rt. Then, saturated aqueous NH4Cl solution (20 ml) wasadded. The products were extracted with toluene. The combined organic phase was washed withbrine, and dried over MgSO4. After the solvent was removed under reduced pressure, the residuewas purified by column chromatography on silica gel with hexane to give pale yellow oil of 7(2.0 g, 81%).
80%	With copper(l) iodide; diisopropylamine Heating;
75%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine at 0 - 60℃; for 22h; Inert atmosphere;
67%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine In benzene for 15.5h;
66.4%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 25℃; for 16h; Inert atmosphere;
	With copper(l) iodide; triethylamine; triphenylphosphine In tetrahydrofuran at 40℃; for 14h;
	With copper(l) iodide; N-butylamine In diethyl ether
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In benzene at 80℃; for 20h; Inert atmosphere;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 60℃; for 24h; Inert atmosphere;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 20℃; for 16h; Inert atmosphere; Schlenk technique;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine at 25℃; for 4h; Inert atmosphere;

Reference： [1]Alabugin, Igor V.; Kovalenko, Serguei V. [Journal of the American Chemical Society, 2002, vol. 124, # 31, p. 9052 - 9053]
[2]He, Feifei; Jana, Sripati; Koenigs, Rene M. [Organic Letters, 2020]
[3]Resa, Sandra; Miguel, Delia; Guisán-Ceinos, Santiago; Mazzeo, Giuseppe; Choquesillo-Lazarte, Duane; Abbate, Sergio; Crovetto, Luis; Cárdenas, Diego J.; Carreño, M. Carmen; Ribagorda, María; Longhi, Giovanna; Mota, Antonio J.; Álvarez de Cienfuegos, Luis; Cuerva, Juan M. [Chemistry - A European Journal, 2018, vol. 24, # 11, p. 2653 - 2662]
[4]Škoch, Karel; Daniliuc, Constantin G.; Erker, Gerhard; Kehr, Gerald [Chemical Communications, 2020, vol. 56, # 81, p. 12178 - 12181]
[5]Andreasson, Måns; Erdelyi, Mate; Németh, Flóra Boróka; Pápai, Imre; Sethio, Daniel; von der Heiden, Daniel [Organic and Biomolecular Chemistry, 2021, vol. 19, # 38, p. 8307 - 8323]
[6]Juricek, Michal; Stout, Kathleen; Kouwer, Paul H. J.; Rowan, Alan E. [Organic Letters, 2011, vol. 13, # 13, p. 3494 - 3497]
[7]Ding, Nan; Li, Haiwei; Feng, Xiao; Wang, Qianyou; Wang, Shan; Ma, Li; Zhou, Junwen; Wang, Bo [Journal of the American Chemical Society, 2016, vol. 138, # 32, p. 10100 - 10103]
[8]Liedtke, Rene; Harhausen, Marcel; Froehlich, Roland; Kehr, Gerald; Erker, Gerhard [Organic Letters, 2012, vol. 14, # 6, p. 1448 - 1451]
[9]Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. [Synthesis, 1980, # 8, p. 627 - 630]
[10]Reine, Pablo; Campaña, Araceli G.; Alvarez De Cienfuegos, Luis; Blanco, Victor; Abbate, Sergio; Mota, Antonio J.; Longhi, Giovanna; Miguel, Delia; Cuerva, Juan M. [Chemical Communications, 2019, vol. 55, # 72, p. 10685 - 10688]
[11]Hasegawa, Masashi; Iyoda, Masahiko [Bulletin of the Chemical Society of Japan, 2020, vol. 93, # 1, p. 154 - 162]
[12]Zhou, Qin; Carroll, Patrick J.; Swager, Timothy M. [Journal of Organic Chemistry, 1994, vol. 59, # 6, p. 1294 - 1301]
[13]Li, Jian-Rong; Yakovenko, Andrey A.; Lu, Weigang; Timmons, Daren J.; Zhuang, Wenjuan; Yuan, Daqiang; Zhou, Hong-Cai [Journal of the American Chemical Society, 2010, vol. 132, # 49, p. 17599 - 17610]
[14]Yasuike, Shuji; Kiharada, Tsutomu; Tsuchiya, Takashi; Kurita, Jyoji [Chemical and pharmaceutical bulletin, 2003, vol. 51, # 11, p. 1283 - 1288]
[15]LaBeaume, Paul; Wager, Krista; Falcone, Danielle; Li, Jane; Torchilin, Vladimir; Castro, Curtis; Holewa, Coleen; Kallmerten, Amy E.; Jones, Graham B. [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 17, p. 6292 - 6300]
[16]Poloukhtine, Andrei; Popik, Vladimir V. [Chemical Communications, 2005, # 5, p. 617 - 619]
[17]Lin, Chi-Fong; Lo, Yu-Hsiang; Hsieh, Ming-Chu; Chen, Yi-Hua; Wang, Jeh-Jeng; Wu, Ming-Jung [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 10, p. 3565 - 3575]
[18]Location in patent: experimental part Manbeck, Gerald F.; Brennessel, William W.; Evans, Christopher M.; Eisenberg, Richard [Inorganic Chemistry, 2010, vol. 49, # 6, p. 2834 - 2843]
[19]Li, De-Yao; Wei, Yin; Shi, Min [Chemistry - A European Journal, 2013, vol. 19, # 46, p. 15682 - 15688]
[20]Bucher, Janina; Stösser, Tim; Rudolph, Matthias; Rominger, Frank; Hashmi, A. Stephen K. [Angewandte Chemie - International Edition, 2015, vol. 54, # 5, p. 1666 - 1670][Angew. Chem., 2014]
[21]Hirai, Yuichi; Nakanishi, Takayuki; Kitagawa, Yuichi; Fushimi, Koji; Seki, Tomohiro; Ito, Hajime; Fueno, Hiroyuki; Tanaka, Kazuyoshi; Satoh, Toshifumi; Hasegawa, Yasuchika [Inorganic Chemistry, 2015, vol. 54, # 9, p. 4364 - 4370]

9
[ 615-42-9 ]
[ 6974-97-6 ]
1,2-bis(4,7-dimethyl-1-indenyl)benzene [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,1998,vol. 568,p. 41 - 51

10
[ 615-42-9 ]
[ 107-19-7 ]
[ 116510-02-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: 1,2-Diiodobenzene With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride In tetrahydrofuran for 0.0833333h; Inert atmosphere; Stage #2: propargyl alcohol With diethylamine In tetrahydrofuran at 20℃; Inert atmosphere;
62%	Stage #1: 1,2-Diiodobenzene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran for 0.0833333h; Inert atmosphere; Stage #2: propargyl alcohol With diethylamine In tetrahydrofuran Inert atmosphere;	2.1 Step 1. Preparation of 3,3'-(1,2-phenylene)bis(prop-2-yn-1-ol) (Compound 1a) Synthesis of 3,3'-(1,2-phenylene)bis(prop-2-yn-1-ol) was prepared according to the procedures reported in J. Phys. Org. Chem., 2011, 24, 969-975. In a dry 3-neck 2 L round bottom flask with a mechanical stirrer attached was added 1,2 diiodobenzene (36.0 g; 109.1 mmol) in dry THF (720 mL) under nitrogen. The solution was evacuated and refilled with nitrogen twice. Bis(triphenylphosphine)palladium dichloride (7.2 g; 10.3 mmol, 0.09 mol. %) was added in one portion. Again the system was evacuated and refilled with nitrogen twice. Copper (I) iodide (1.2 g; 6.5 mmol, 0.06 mol. %) was added and the dark orange mixture was stirred for 5 minutes. Propargyl alcohol (25.4 mL; 436.3 mmol, 4.0 eq.) was added quickly via a syringe followed by diethylamine (72 mL). The dark brown solution was wrapped in aluminum foil and stirred overnight. Thin Layer Chromatography (TLC) (95:5 hexane:ethyl acetate with UV detection) indicated a minor amount of starting material remained. Propargyl alcohol (12.7 mL; 218.1 mmol, 2.0 eq.) was added followed by diethylamine (36 mL). After another 48 hours (72 hours total) the reaction solution was concentrated in vacuo to recover a viscous oil as crude product. The crude product was dissolved (with warming) in 800 mL of ethyl acetate and 1M HCl (250 mL). The mixture was filtered and poured into a 2 L separatory funnel. The contents were shaken and separated. The organic layer was washed with water (2*200 mL) and brine (250 mL). The organic layer was concentrated in vacuo to recover 22.0 g of a brown oil, which was pre-adsorbed onto silica and isolated using silica gel chromatography. The product was isolated using a continuous gradient of 40 to 70 vol. % ethyl acetate:hexane over 35 minutes to recover 12.7 g (62%) of desired product. 1H-NMR, 400 MHz, CDCl3, ppm; 7.4-7.3 (m, 2H), 7.2 (m, 2H), 4.5 (s, 4H) and 3.5 (br, 2H). 13 C-NMR, 100 MHz, CDCl3, ppm; 131.5, 128.0, 125.2, 91.6, 84.2 and 51.4.
60%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine In tetrahydrofuran at 20℃; Inert atmosphere;	General method for the preparation of 6 and 14: General procedure: Bis(triphenylphosphine)palladium dichloride (5 mol%, 106 mg, 0.15 mmol) was added to a stirred solution of o-diiodobenzene (3.03 mmol) in dry degassed THF (20 mL) under N2 atmosphere. The solution was degassed with a flow of N2, and powdered copper(I) iodide (5 mol%, 29 mg, 0.15 mmol) was added to the mixture. After 5 min of stirring, propargyl alcohol (0.72 g, 12.70 mmol, 1 mL) was added to the mixture, followed by diethyl amine (10 mL). The reaction vessel was purged with N2 gas, sealed, and left with overnight stirring at room temperature. Another four equivalents of propargyl alcohol and 5 mL of diethyl amine were added to the reaction mixture. After two more days of stirring, the reaction mixture was extracted through ethyl acetate (3×30 mL) and washed with brine. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by column chromatography (3:1 Pet ether: ethyl acetate) on silica gel as yellowish oil with a 60% yield (for compound 6) and 59% yield (for compound 14).

40%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ Reflux;	1 33a: 3,3′-(1,2-Phenylene)bis(prop-2-yn-1-ol) 33a: 3,3′-(1,2-Phenylene)bis(prop-2-yn-1-ol) (0290) To the degased solution of 1,2-diiodobenzene (1 eq., 661 mg, 0.262 mL, 2 mmol) and propargylic alcohol (2.3 eq., 272 μL, 4.61 mmol) in butyl amine (15.8 mL), Pd(PPh3)4 (4%, 92.6 mg, 0.0801 mmol) was added and the obtained reaction mass was refluxed overnight. Solvents were evaporated and the obtained crude product was purified by flash chromatography (20 minutes gradient EtOAc/Cyclohexane) to yield 33a (150 mg, 0.8 mmol, 40%) as a brownish solid. (0291) 1H NMR (400 MHz, METHANOL-d4) δ 7.38-7.53 (m, 2H), 7.25-7.38 (m, 2H), 4.48 (s, 4H); 13C NMR (101 MHz, METHANOL-d4) d 135.6, 131.9, 129.2, 95.6, 86.6, 53.9; ESI-MS: C12H11O2+ [M+H]+, 187.1; found 187.1.
40%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide for 2h; Inert atmosphere;
36%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-butylamine In diethyl ether for 5h;

Reference： [1]Location in patent: experimental part Zhegalova, Natalia G.; Popik, Vladimir V. [Journal of Physical Organic Chemistry, 2011, vol. 24, # 10, p. 969 - 975]
[2]Current Patent Assignee: EXXON MOBIL CORP - US2019/194028, 2019, A1 Location in patent: Paragraph 0114; 0115
[3]Ghosh, Debaki; Basu, Souradeep; Singha, Monisha; Das, Joyee; Bhattacharya, Prabuddha; Basak, Amit [Tetrahedron Letters, 2017, vol. 58, # 21, p. 2014 - 2018]
[4]Current Patent Assignee: UNIVERSITY OF STRASBOURG; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - US2016/145199, 2016, A1 Location in patent: Paragraph 0290-0291
[5]Koniev, Oleksandr; Dovgan, Igor; Renoux, Brigitte; Ehkirch, Anthony; Eberova, Jitka; Cianférani, Sarah; Kolodych, Sergii; Papot, Sébastien; Wagner, Alain [MedChemComm, 2018, vol. 9, # 5, p. 827 - 830]
[6]Wu, Ming-Jung; Lin, Chi-Fong; Chang, Li-Juan; Jing, Pao-Tzu; Duh, Tsai-Hui; Tseng, Wuan-Ting; Lee, Fang-Chen; Wang, Shan-Shue; Chang, Hsueh-O. [Journal of the Chinese Chemical Society, 1998, vol. 45, # 6, p. 783 - 788]

11
[ 1614-12-6 ]
[ 615-42-9 ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 1013 - 1023

12
[ 615-42-9 ]
[ 263012-63-1 ]
[ 263012-62-0 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 1257 - 1272

13
[ 615-42-9 ]
Me₃SiX [ No CAS ]
[ 59376-64-6 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 636 - 640

14
[ 615-42-9 ]
[ 244205-40-1 ]
[ 98470-26-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 1,2-Diiodobenzene; (2-bromophenyl)boronic acid With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine In tetrahydrofuran Schlenk technique; Inert atmosphere; Stage #2: With potassium hydroxide In tetrahydrofuran at 60℃; for 24h; Schlenk technique; Inert atmosphere;
73%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; sodium hydroxide In water; nitrobenzene at 70℃; for 48h; Inert atmosphere;	o-Diiodobenzene (1.75 g, 5.3 mmol), 2-bromophenylboronic acid (10.36 g, 52 mmol), and PPh3 (3.42 g, 13 mmol) were added into a mixture of nitrobenzene (300 mL) and NaOH (320 mL, 2.5 M). The mixture was bubbled with N2 for 15 min. Pd(PPh3)4 (485 mg, 0.53 mmol) was added and the mixture was bubbled for 10 mins. The mixture was heated to 70° C. for 2 days. The mixture was partitioned with hexane and brine. The organic layer was evaporated under reduced pressure and the residue was purified by column chromatography using hexane as the eluent to yield 2,2"-dibromo-1,1':2',1"-terphenyl as a white oil (1.5 g, 73%) .
65.7%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In toluene for 5h; Reflux;	1 Synthesis of Intermediate A ,2-diiodobenzene (1 eq)And (2-bromophenyl)boronic acid (2.1 eq)Was dissolved in 500 ml of toluene.Pd(PPh3)4 (0.02eq) was added.400 ml of toluene and 2M K2CO3After adding 70 ml of saturated solution,The mixture was stirred under reflux for 5 hours.After the reaction is complete,Methylene chloride (MC) 400 mlAnd distilled water 150mlAfter washing and extracting withAfter removing the solventThe produced solid was purified by column chromatography to obtain the desired intermediate A (yield 65.7%).From the molecular weight measured by the mass spectrometer,It was confirmed to be Intermediate A.

65%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammomium bromide; sodium hydroxide In water; toluene at 80℃; for 12h; Inert atmosphere;	10.1 5) Synthesis of Intermediate 3-8: General procedure: Under a nitrogen atmosphere, (7.0g, 20mmol) of compound 3-6 and (6.2g, 20mmol) of compound 3-7,(1.38g, 1.2mmol) tetrakis(triphenylphosphorus) palladium,(1.3g, 4mmol) tetrabutylammonium bromide, (0.8g, 20mmol) sodium hydroxide, (10mL) water and (80mL) toluene were added to a 250mL three-neck flask, heated at 80°C and stirred for 12 hours,After finishing the reaction, the reaction solution was rotary evaporated to remove most of the solvent, washed with dichloromethane dissolved in water 3 times, and the organic phase was collected, mixed with silica gel, and purified by column. The yield was 80%.
60%	With sodium hydroxide; triphenylphosphine In nitrobenzene at 60℃; for 576h;

Reference： [1]Barrett, Brittany J.; Iluc, Vlad M. [Organometallics, 2017, vol. 36, # 3, p. 730 - 741]
[2]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US2018/114929, 2018, A1 Location in patent: Paragraph 0107-0108
[3]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - JP2020/90489, 2020, A Location in patent: Paragraph 0127-0128
[4]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - CN111875609, 2020, A Location in patent: Paragraph 0168; 0172; 0177; 0256-0261
[5]King, Benjamin T.; Kroulik, Jiri; Robertson, Charles R.; Rempala, Pawel; Hilton, Cameron L.; Korinek, Justin D.; Gortari, Lisa M. [Journal of Organic Chemistry, 2007, vol. 72, # 7, p. 2279 - 2288]

15
[ 615-42-9 ]
[ 177171-16-3 ]
[ 929700-49-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In diethylene glycol dimethyl ether; water; at 95℃; for 15h;Inert atmosphere;	Separately, 1,2-diiodobenzene (24.4 g), <strong>[177171-16-3]3-trimethylsilylphenylboronic acid</strong> (30 g), sodium hydroxide (8.8 g), tetrakis(triphenylphosphine)palladium(0) (4.3 g), diethylene glycol dimethyl ether (160 ml), and water (40 ml) were added to a nitrogen-substituted reaction vessel. The mixture was heated, and stirred at 95C for 15 hours. After cooling the mixture to room temperature, water (100 ml) was added, and the organic layer was collected by separation. The organic layer was washed two times with water (100 ml), dried over anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was purified by column chromatography (support: silica gel, eluent: n-hexane) to obtain a white powder of 3,3''-bis(trimethylsilyl)-1,1':2',1''-terphenyl (23.3 g; yield 84%).
84%	With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In diethylene glycol dimethyl ether; water; at 95℃; for 15h;Inert atmosphere;	Separately, 1,2-diiodobenzene (24.4 g), <strong>[177171-16-3]3-trimethylsilylphenylboronic acid</strong> (30 g), sodium hydroxide (8.8 g), tetrakis(triphenylphosphine)palladium(0) (4.3 g), diethylene glycol dimethyl ether (160 ml), and water (40 ml) were added to a nitrogen-substituted reaction vessel. The mixture was heated, and stirred at 95C for 15 hours. After cooling the mixture to room temperature, water (100 ml) was added, and the organic layer was collected by separation. The organic layer was washed two times with water (100 ml), dried over anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was purified by column chromatography (support: silica gel, eluent: n-hexane) to obtain a white powder of 3,3'-bis(trimethylsilyl)-1,1':2',1'-terphenyl (23.3 g; yield 84%).
84%	With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In diethylene glycol dimethyl ether; water; at 95℃; for 15h;Inert atmosphere;	On the other hand, in a reaction vessel purged with nitrogen,24.4 g of 1,2-diiodobenzene,30 g of <strong>[177171-16-3]3-trimethylsilylphenylboronic acid</strong>,8.8 g of sodium hydroxide,4.3 g of tetrakis (triphenylphosphine) palladium (0)Diethylene glycol dimethyl ether 160 ml,40 ml of water was added and the mixture was heated and stirred at 95 C. for 15 hours.After cooling to room temperature,100 ml of water was added,An organic layer was collected by performing a liquid separating operation.After washing the organic layer twice with 100 ml of water,It was dehydrated over anhydrous magnesium sulfate,The crude product was obtained by concentration.The crude product was purified by column chromatography (carrier: silica gel, eluent: n-hexane)3,3 "-bis (trimethylsilyl) -1,1 ': 2', 1 "-terphenylWhite powder23.3 g (yield 84%) was obtained.

Reference： [1]Patent: EP2679581,2014,A1 .Location in patent: Paragraph 0128
[2]Patent: EP2679582,2014,A1 .Location in patent: Paragraph 0100
[3]Patent: JP6126577,2017,B2 .Location in patent: Paragraph 0115
[4]Journal of Organic Chemistry,2007,vol. 72,p. 2279 - 2288

16
[ 615-42-9 ]
[ 21792-52-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: n-BuNH₂; CuI / Pd(PPh₃)4 / diethyl ether 2: 86 percent / potassium carbonate / methanol
	Multi-step reaction with 2 steps 1: 80 percent / CuI, NH(iPr)2 / (PPh₃)2PdCl₂ / Heating 2: 90 percent / aq. KOH / tetrahydrofuran; methanol / Ambient temperature
	Multi-step reaction with 2 steps 1: 85 percent / bis<triphenylphosphine>palladium dichloride, copper⁽¹⁾ iodide / various solvent(s) / 60 °C 2: 74 percent / potassium hydroxide aq. / methanol

	Multi-step reaction with 3 steps 1: K₂CO₃, Cu, Py 2: aq. HCl 3: KOH / 1.5 Torr / Heating
	Multi-step reaction with 2 steps 1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 24 h / 60 °C / Inert atmosphere 2: potassium carbonate; methanol / dichloromethane / 1 h / 25 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / triethylamine / 16 h / 20 °C / Inert atmosphere; Schlenk technique 2: potassium carbonate / methanol / 0.33 h / 20 °C / Inert atmosphere; Schlenk technique
	Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine / 4 h / 25 °C / Inert atmosphere 2: potassium carbonate / methanol; water / 3 h
	Multi-step reaction with 2 steps 1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 20 °C / Inert atmosphere 2: tri tert-butylphosphoniumtetrafluoroborate / tetrahydrofuran / 20 °C
	Multi-step reaction with 2 steps 1: trans-bis(triphenylphosphine)palladium dichloride; copper(l) iodide; triethylamine / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 1 h / 20 °C
	Multi-step reaction with 2 steps 1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / benzene / 13 h / 20 °C / Inert atmosphere 2: potassium carbonate; methanol / 0.17 h / 20 °C
	Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine / 0.25 h / 110 °C / Inert atmosphere; Sealed tube; Microwave irradiation 2: potassium carbonate / tetrahydrofuran; methanol / 2.5 h / 20 °C

Reference： [1]Lin, Chi-Fong; Lo, Yu-Hsiang; Hsieh, Ming-Chu; Chen, Yi-Hua; Wang, Jeh-Jeng; Wu, Ming-Jung [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 10, p. 3565 - 3575]
[2]Zhou, Qin; Carroll, Patrick J.; Swager, Timothy M. [Journal of Organic Chemistry, 1994, vol. 59, # 6, p. 1294 - 1301]
[3]Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. [Synthesis, 1980, # 8, p. 627 - 630]
[4]Shvartsberg,M.S. et al. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1971, vol. 20, p. 1209 - 1212][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1971, vol. 20, # 6, p. 1306 - 1310]
[5]Li, De-Yao; Wei, Yin; Shi, Min [Chemistry - A European Journal, 2013, vol. 19, # 46, p. 15682 - 15688]
[6]Bucher, Janina; Stösser, Tim; Rudolph, Matthias; Rominger, Frank; Hashmi, A. Stephen K. [Angewandte Chemie - International Edition, 2015, vol. 54, # 5, p. 1666 - 1670][Angew. Chem., 2014]
[7]Hirai, Yuichi; Nakanishi, Takayuki; Kitagawa, Yuichi; Fushimi, Koji; Seki, Tomohiro; Ito, Hajime; Fueno, Hiroyuki; Tanaka, Kazuyoshi; Satoh, Toshifumi; Hasegawa, Yasuchika [Inorganic Chemistry, 2015, vol. 54, # 9, p. 4364 - 4370]
[8]Resa, Sandra; Miguel, Delia; Guisán-Ceinos, Santiago; Mazzeo, Giuseppe; Choquesillo-Lazarte, Duane; Abbate, Sergio; Crovetto, Luis; Cárdenas, Diego J.; Carreño, M. Carmen; Ribagorda, María; Longhi, Giovanna; Mota, Antonio J.; Álvarez de Cienfuegos, Luis; Cuerva, Juan M. [Chemistry - A European Journal, 2018, vol. 24, # 11, p. 2653 - 2662]
[9]Reine, Pablo; Campaña, Araceli G.; Alvarez De Cienfuegos, Luis; Blanco, Victor; Abbate, Sergio; Mota, Antonio J.; Longhi, Giovanna; Miguel, Delia; Cuerva, Juan M. [Chemical Communications, 2019, vol. 55, # 72, p. 10685 - 10688]
[10]Hasegawa, Masashi; Iyoda, Masahiko [Bulletin of the Chemical Society of Japan, 2020, vol. 93, # 1, p. 154 - 162]
[11]Andreasson, Måns; Erdelyi, Mate; Németh, Flóra Boróka; Pápai, Imre; Sethio, Daniel; von der Heiden, Daniel [Organic and Biomolecular Chemistry, 2021, vol. 19, # 38, p. 8307 - 8323]

17
[ 615-42-9 ]
[ 6342-87-6 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 7876 - 7888

18
[ 615-42-9 ]
[ 89694-45-1 ]
[ 869499-76-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; for 80h;Heating / reflux;	A mixture of 1,2-diiodobenzene (35g, 106mmol), <strong>[89694-45-1]5-bromo-2-methyloxyphenylboronic acid</strong> (20g, 85mmol), tetrakis (triphenylphosphine) palladium(0)(1.0g) and potassium carbonate (11.Og) in 1,2 dimethoxyethane (120ml) was refluxed under nitrogen for 80 hours. The reaction mixture was filtered through celite and flash chromatographed, eluting with dichloromethane/iso-hexane (1/4) to give the title compound. (19.0g). LC/MS Rt=3.9 min.

Reference： [1]Patent: WO2005/108369,2005,A1 .Location in patent: Page/Page column 35-36

19
[ 615-42-9 ]
[ 25015-63-8 ]
[ 857934-82-8 ]
[ 269410-07-3 ]
[ 24388-23-6 ]

Reference： [1]Electrochimica Acta,2005,vol. 50,p. 4897 - 4901

20
[ 615-42-9 ]
[ 16356-02-8 ]
[ 1047668-20-1 ]

Yield	Reaction Conditions	Operation in experiment
73%	With dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II); 1,2-bis-(diphenylphosphino)ethane; zinc In acetonitrile at 100℃; for 48h; Inert atmosphere;

Reference： [1]Hsieh, Jen-Chieh; Cheng, Chien-Hong [Chemical Communications, 2008, # 26, p. 2992 - 2994]

21
[ 471-29-4 ]
[ 615-42-9 ]
[ 17228-38-5 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5742 - 5745

22
[ 5699-40-1 ]
[ 615-42-9 ]
[ 21202-05-1 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5742 - 5745

23
[ 615-42-9 ]
[ 6145-42-2 ]
[ 2851-13-0 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5742 - 5745

24
[ 615-42-9 ]
[ 41908-11-6 ]
[ 1193603-05-2 ]

Reference： [1]Synthesis,2009,p. 2818 - 2824

25
[ 615-42-9 ]
[ 201230-82-2 ]
[ 107-11-9 ]
[ 5428-09-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene at 110℃; for 24h; Ionic liquid; Autoclave;

Reference： [1]Cao, Hong; Alper, Howard [Organic Letters, 2010, vol. 12, # 18, p. 4126 - 4129]

26
[ 615-42-9 ]
[ 201230-82-2 ]
[ 98-80-6 ]
[ 25187-00-2 ]

Yield	Reaction Conditions	Operation in experiment
31%	Stage #1: 1,2-Diiodobenzene; phenylboronic acid With potassium carbonate In toluene for 0.166667h; Autoclave; Stage #2: carbon monoxide In toluene at 100℃; for 10h; Autoclave;

Reference： [1]Location in patent: experimental part Qureshi, Ziyauddin S.; Deshmukh, Krishna M.; Tambade, Pawan J.; Bhanage, Bhalchandra M. [Synthesis, 2011, # 2, p. 243 - 250]

27
[ 615-42-9 ]
[ 92-85-3 ]

Yield	Reaction Conditions	Operation in experiment
82%	With 1,10-Phenanthroline; potassium carbonate; sulfur; In dimethyl sulfoxide; at 90℃; for 12h;	The present invention is achieved in such a way that,To a 25 mL round bottom flask was added o-diiodobenzene (0.5 mmol)Sulfur powder (0.5 mmol),Cuprous iodide (0.05 mmol),1,10-phenanthroline (0.1 mmol),Potassium carbonate (1.0 mmol) andDimethyl sulfoxide (2 mL).The resulting mixture was stirred at 90 C for 12 hours.After cooling to room temperature, add 10 mL of water to the system,Then extracted with ethyl acetate (3 x 10 mL) and dried over anhydrous sodium sulfate. After the solvent was distilled off,The resulting residue was purified by silica gel column chromatography in 82% yield.
68%	With 1,10-Phenanthroline; potassium carbonate; sulfur; copper(I) bromide; In dimethyl sulfoxide; at 90℃; for 24h;Inert atmosphere;	Under the protection of nitrogen, 8.3g (25.2mmol) o-diiodobenzene, 1.6g (50mmol) sulfur powder, 10.4g (75mmol) potassium carbonate, 0.36g (2.5mmol) copper bromide, 2.5g ( 12.5mmol)1,10-phenanthroline was added to a 100mL three-necked flask, 40mL of dimethyl sulfoxide was added thereto, and heated to 90 C with stirring for 24 hours,The temperature was lowered, the reaction was quenched with sodium thiosulfate solution, the reaction liquid was extracted with ethyl acetate several times, the organic phase was dried over magnesium sulfate and concentrated under reduced pressure,The resulting solid was purified by silica gel column chromatography using methylene chloride and n-heptane (1:10) to obtain compound 100-1 (3.7 g, yield 68%).

Reference： [1]Patent: CN104844565,2017,B .Location in patent: Paragraph 0006; 0009; 0010; 0011
[2]Patent: CN111004207,2020,A .Location in patent: Paragraph 0225-0226
[3]Synlett,2011,p. 134 - 138
[4]Journal of Organic Chemistry,2013,vol. 78,p. 5001 - 5006

28
[ 615-42-9 ]
[ 71-43-2 ]
[ 84-15-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With quinoline-1-amino-2-carboxylic acid; potassium <i>tert</i>-butylate at 120℃; for 24h; Sealed tube; Inert atmosphere;
70%	With silver fluoride at 20℃; for 48h; Irradiation; Inert atmosphere;

Reference： [1]Qiu, Yatao; Liu, Yanghan; Yang, Kai; Hong, Wenkun; Li, Zheng; Wang, Zhaoyang; Yao, Zhiyi; Jiang, Sheng [Organic Letters, 2011, vol. 13, # 14, p. 3556 - 3559]
[2]Wu, Wenli; Cui, Enxin; Zhang, Yun; Zhang, Chen; Zhu, Feng; Tung, Chen-Ho; Wang, Yifeng [ACS Catalysis, 2019, vol. 9, # 7, p. 6335 - 6341]

29
[ 615-42-9 ]
[ 201230-82-2 ]
[ 616-34-2 ]
[ 23244-58-8 ]
[ 69238-60-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 31% 2: 48%	With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; for 72h;	4.4. Aminocarbonylation of 1,2-diiodobenzene (5) in the presence of primary and secondary amines under atmospheric carbon monoxide pressure In a typical experiment Pd(OAc)2 (5.6 mg, 0.025 mmol), PPh3 (13.1 mg, 0.05 mmol), 1,2-diiodobenzene (330 mg, 1 mmol), 6 mmol of tert-butylamine (f) (or 2.2 mmol of amino acid methyl ester hydrochloride (g, h) or 3 mmol of secondary amine (i, j)) and 0.5 mL triethylamine were dissolved in DMF (10 mL) under argon in a 100 mL three-necked flask equipped with a gas inlet, reflux condenser with a balloon at the top. The atmosphere was changed to carbon monoxide. The reaction was conducted for the given reaction time upon stirring at 50 °C and analysed by GC-MS. The work-up procedure was identical with those described in Section refPreviewPlaceHolder4.3.

Reference： [1]Location in patent: experimental part Marosvölgyi-Haskó, Diána; Petz, Andrea; Takács, Attila; Kollár, László [Tetrahedron, 2011, vol. 67, # 47, p. 9122 - 9128]

30
[ 615-42-9 ]
[ 108-95-2 ]
[ 34883-46-0 ]

Yield	Reaction Conditions	Operation in experiment
42%	With copper(I) oxide; caesium carbonate; imidazole-4-carboxylic acid; In acetonitrile; at 80℃; for 24h;	General procedure: To a screw-capped vial (4-mL) were added Cs2CO3 (1.0 mmol, 325 mg), Cu2O (0.005 mmol, 0.7 mg), 1H-imidazole-4-carboxylic acid (0.01 mmol, 1.1 mg) and acetonitrile (0.25 mL). The vial was sealed with septum and allowed to stir for a while; the iodoarene (0.5 mmol) and phenol (0.6 mmol) were then injected into the reaction mixture via a syringe. The septum was removed, and the vial was sealed with a screw cap. The reaction mixture was stirred at 80 oC for 24 h. The crude reaction mixture was diluted with CH2Cl2, filtered through a thin Celite pad, and concentrated in vacuo. The residue was isolated through a column chromatography by using hexane and ethyl acetate as eluent to give the pure product. Products 3a-v were obtained according to this procedure. The known structures were characterized by the 1H NMR and 13C NMR of reported literatures.1-3 Spectral data, 1H NMR and 13C NMR spectra for all the new compounds are listed below.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 71 - 75

31
[ 14003-16-8 ]
[ 615-42-9 ]
[ 201230-82-2 ]
[ 62675-16-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 1,4-diaza-bicyclo[2.2.2]octane; palladium 10% on activated carbon In toluene at 120℃; for 4h; Autoclave;
85%	With triethylamine In toluene at 100℃; for 6h; Autoclave;	General procedure carbonylative cyclization ofmethyl-2-iodobenoate/1,2-diiodo benzene for the synthesis ofN-substituted isoindole-1,3-diones using ImmPd-IL as a catalyst General procedure: General procedure carbonylative cyclization ofmethyl-2-iodobenoate/1,2-diiodo benzene for the synthesis ofN-substituted isoindole-1,3-diones using ImmPd-IL as a catalystIn a 100 mL stainless steel autoclave, methyl-2-iodobenoate/1,2-diiodobenzene (1 mmol), aryl amine (2 mmol), ImmPd-IL(2 mol%), toluene (10 mL) and Et3N (2.5 mmol) were added. Theautoclave was closed, purged three times with nitrogen followedwith carbon monoxide, and then pressurized with 1 atm of CO andheated at 100C for 6 h. After completion of reaction the reac-tor was cooled to room temperature, the remaining CO gas wascarefully vented, and the reactor was opened. The reactor vesselwas thoroughly washed with ethyl acetate (10-15 mL) to removeany traces of product and catalyst if present. The catalyst was fil-tered and the reaction mixture was evaporated under vacuum. Theresidue obtained was purified by column chromatography (silicagel, 60-120 mesh; petroleum ether/ethyl acetate, 95:05) to affordthe desired product. The products were confirmed by GC, GC-MS,1H NMR and13C NMR spectroscopic techniques. The purity of com-pounds was determined by GC-MS analysis.

Reference： [1]Khedkar, Mayur V.; Khan, Shoeb R.; Sawant, Dinesh N.; Bagal, Dattatraya B.; Bhanage, Bhalchandra M. [Advanced Synthesis and Catalysis, 2011, vol. 353, # 18, p. 3415 - 3422]
[2]Khedkar, Mayur V.; Shinde, Ajinkya R.; Sasaki, Takehiko; Bhanage, Bhalchandra M. [Journal of Molecular Catalysis A: Chemical, 2014, vol. 385, p. 91 - 97]

32
[ 615-42-9 ]
[ 201230-82-2 ]
[ 108-91-8 ]
[ 2133-65-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With 1,4-diaza-bicyclo[2.2.2]octane; palladium 10% on activated carbon In toluene at 120℃; for 2h; Autoclave;
93%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained

Reference： [1]Khedkar, Mayur V.; Khan, Shoeb R.; Sawant, Dinesh N.; Bagal, Dattatraya B.; Bhanage, Bhalchandra M. [Advanced Synthesis and Catalysis, 2011, vol. 353, # 18, p. 3415 - 3422]
[2]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]

33
[ 615-42-9 ]
[ 201230-82-2 ]
[ 100-01-6 ]
[ 31604-39-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained
50%	With 1,4-diaza-bicyclo[2.2.2]octane; palladium 10% on activated carbon In toluene at 120℃; for 2h; Autoclave;

Reference： [1]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]
[2]Khedkar, Mayur V.; Khan, Shoeb R.; Sawant, Dinesh N.; Bagal, Dattatraya B.; Bhanage, Bhalchandra M. [Advanced Synthesis and Catalysis, 2011, vol. 353, # 18, p. 3415 - 3422]

34
[ 615-42-9 ]
[ 201230-82-2 ]
[ 109-73-9 ]
[ 1515-72-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 1,4-diaza-bicyclo[2.2.2]octane; palladium 10% on activated carbon In toluene at 120℃; for 2h; Autoclave;
91%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained

Reference： [1]Khedkar, Mayur V.; Khan, Shoeb R.; Sawant, Dinesh N.; Bagal, Dattatraya B.; Bhanage, Bhalchandra M. [Advanced Synthesis and Catalysis, 2011, vol. 353, # 18, p. 3415 - 3422]
[2]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]

35
[ 615-42-9 ]
[ 201230-82-2 ]
[ 100-46-9 ]
[ 2142-01-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 1,4-diaza-bicyclo[2.2.2]octane; palladium 10% on activated carbon In toluene at 120℃; for 2h; Autoclave;
92%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained

Reference： [1]Khedkar, Mayur V.; Khan, Shoeb R.; Sawant, Dinesh N.; Bagal, Dattatraya B.; Bhanage, Bhalchandra M. [Advanced Synthesis and Catalysis, 2011, vol. 353, # 18, p. 3415 - 3422]
[2]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]

36
[ 615-42-9 ]
[ 105-36-2 ]
[ 100-47-0 ]
[ 36779-16-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: ethyl bromoacetate; benzonitrile With methanesulfonic acid; zinc In tetrahydrofuran for 2h; Reflux; Inert atmosphere; Stage #2: 1,2-Diiodobenzene With copper(l) iodide; 1,10-Phenanthroline; potassium <i>tert</i>-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 20 - 120℃; for 24h; Inert atmosphere;
76%	Stage #1: ethyl bromoacetate; benzonitrile With methanesulfonic acid; zinc In tetrahydrofuran Reflux; Inert atmosphere; Stage #2: 1,2-Diiodobenzene With copper(l) iodide; 1,10-Phenanthroline; potassium <i>tert</i>-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Kim, Juhyun; Chun, Yusung; Shin, Hyunik; Lee, Sang-Gi [Synthesis, 2012, vol. 44, # 12, p. 1809 - 1817]
[2]Location in patent: experimental part Kim, Ju Hyun; Lee, Sang-Gi [Synthesis, 2012, vol. 44, # 10, p. 1464 - 1476]

37
[ 615-42-9 ]
[ 71-43-2 ]
[ 84-15-1 ]
[ 2113-51-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 40% 2: 31%	With potassium <i>tert</i>-butylate; vasicine at 20 - 110℃; for 72h; Schlenk technique; Inert atmosphere;	Generalprocedure for arylation of arene with aryl iodides General procedure: Aryl halide (0.5 mmol),vasicine (0.25 mmol) and KOt-Bu (2mmol) were added to Schlenk tube under nitrogen atmosphere at room temperature.Arene (4 ml) was added to reaction mixture using syringe. Sealed tube was thenstirred at 110°C. After cooling to room temperature the reaction mixture wasfiltered to remove inorganic salts. The solvent was evaporated using a rotaryevaporator. The product was purified from reaction mixture by silica gel columnchromatography using n-hexane/ethylacetate as eluent.
1: 32% 2: 17%	With 1-(2-hydroxyethyl)piperazine; potassium <i>tert</i>-butylate at 100℃; for 24h; Sealed tube; Inert atmosphere;

Reference： [1]Sharma, Sushila; Kumar, Manoranjan; Kumar, Vishal; Kumar, Neeraj [Tetrahedron Letters, 2013, vol. 54, # 36, p. 4868 - 4871]
[2]Yadav, Lalit; Tiwari, Mohit K.; Shyamlal, Bharti Rajesh Kumar; Chaudhary, Sandeep [Journal of Organic Chemistry, 2020, vol. 85, # 12, p. 8121 - 8141]

38
[ 615-42-9 ]
[ 98-80-6 ]
[ 84-15-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium fluoride In water; N,N-dimethyl-formamide at 20℃; for 26h;	2.4 General procedure for Suzuki-Miyaura coupling reaction and recycling General procedure: Aryl halide (0.5mmol), phenyl boronic acid (182.25mg, 0.75mmol), KF (116.2mg, 2.0mmol) and Pd NPs 2 (5.3mg, 0.005mmol, 1mol%) were taken in an oven dried reaction tube equipped with magnetic pellet. DMF (1mL) and H2O (1mL) were added to the reaction tube and the reaction mixture was stirred at room temperature under closed atmosphere. The reaction was monitored by TLC. After the starting material was completely consumed, the reaction was stopped and then the solution was extracted with diethyl ether (3×20mL). The organic phase concentrated in vacuum. The crude product was purified by column chromatography using silica gel.
67%	With potassium carbonate In water at 90℃; for 9h;
50%	With potassium carbonate; triphenylphosphine; palladium dichloride at 70℃; for 24h; Sealed tube;	General procedure for Pd-catalyzed coupling betweenequal amount of dihaloarene and arylboronic acid General procedure: A mixture of dihaloarene (0.4 mmol), arylboronicacid (0.4 mmol), K2CO3 (0.8 mmol), PdCl2 (7 mol %),PPh3 (15 mol %), and PEG-400 (2 mL) in a sealed tubewas stirred in air at 70°C for the desired time until completeconsumption of starting material as monitored byTLC. After that the mixture was poured into ethyl acetate,then washed with water, extracted with ethyl acetate, driedby anhydrous Na2SO4, then fi ltered and evaporated undervacuum, the residue was purifi ed by fl ash column chromatography(petroleum ether or petroleum ether/ethylacetate) to afford the corresponding coupling products

Reference： [1]Ganapathy, Dhandapani; Sekar, Govindasamy [Catalysis Communications, 2013, vol. 39, p. 50 - 54]
[2]Maity, Mitasree; Maitra, Uday [Journal of Materials Chemistry A, 2014, vol. 2, # 44, p. 18952 - 18958]
[3]Mao, Jincheng; Li, Ran; He, Yue; Yang, Xiaojiang; Wang, Dingli; Zhang, Yang [Russian Journal of Applied Chemistry, 2016, vol. 89, # 4, p. 663 - 669]

39
[ 623-03-0 ]
[ 615-42-9 ]
[ 1141-35-1 ]

Yield	Reaction Conditions	Operation in experiment
34%	With copper(l) iodide; Acetaldehyde oxime; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 120℃; for 15h; Inert atmosphere; Schlenk technique;	4.3 General procedure for the synthesis of benzoxazoles General procedure: To a suspension of CuI (9.5 mg, 0.05 mmol), K2CO3 (207.3 mg, 1.5 mmol) in toluene (2.0 mL) were added aryl o-dihalides 1 (0.5 mmol), nitrile 2 (1.0 mmol), DMEDA (8.0 μL, 0.075 mmol), acetaldoxime (92.0 μL, 1.5 mmol) under argon. The reaction mixture was stirred for 15 h at 120°C under argon. The solution was cooled to room temperature and the solvent was removed under vacuum. The crude product was purified by column chromatography on silica gel (eluent: petroleum ether/ethyl acetate=30:1) to afford the benzoxazoles 4.

Reference： [1]Zhang, Dong-Xue; Xiang, Shi-Kai; Hu, Hao; Tan, Wen; Feng, Chun; Wang, Bi-Qin; Zhao, Ke-Qing; Hu, Ping; Yang, Hua [Tetrahedron, 2013, vol. 69, # 47, p. 10022 - 10029]

40
[ 615-42-9 ]
[ 17865-11-1 ]
[ 1394123-87-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In diethylene glycol dimethyl ether; water; at 95℃; for 15h;Inert atmosphere;	Comparative Synthesis Example 3 <Synthesis of 4,4'-bis(2,2'-bipyridin-6-yl)-1,1':2',1'-terphenyl (comparative compound 3)> 1,2-Diiodobenzene (20 g), 4-trimethylsilylphenylboronic acid (25 g), sodium hydroxide (7.4 g), tetrakis(triphenylphosphine)palladium(0) (3.6 g), diethylene glycol dimethyl ether (240 ml), and water (60 ml) were added to a nitrogen-substituted reaction vessel. The mixture was heated, and stirred at 95C for 15 hours. Water (100 ml) was added after cooling the mixture to room temperature, and the organic layer was collected by separation. The organic layer was washed two times with water (100 ml), dried over anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was purified by column chromatography (support: silica gel, eluent: n-hexane) to obtain a white powder of 4,4'-bi(trimethylsilyl)-1,1':2',1'-terphenyl (21.1 g; yield 93%).
93%	With tetrakis(triphenylphosphine) palladium(0); In diethylene glycol dimethyl ether; water; at 95℃; for 15h;	Example 3 <Synthesis of 4,4'-bis(2,2'-bipyridin-5-yl)-1,1':2',1'-terphenyl (compound 10)> 1,2-Diiodobenzene (20 g), 4-trimethylsilylphenylboronic acid (25 g), sodium hydroxide (7.4 g), tetrakis(triphenylphosphine)palladium(0) (3.6 g), diethylene glycol dimethyl ether (240 ml), and water (60 ml) were added to a nitrogen-substituted reaction vessel. The mixture was heated, and stirred at 95C for 15 hours. After cooling the mixture to room temperature, water (100 ml) was added, and the organic layer was collected by separation. The organic layer was washed two times with water (100 ml), dried over anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was purified by column chromatography (support: silica gel, eluent: n-hexane) to obtain a white powder of 4,4'-bis(trimethylsilyl)-1,1':2',1'-terphenyl (21.1 g; yield 93%).

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 10356 - 10360
Angew. Chem.,2015,vol. 127,p. 10497 - 10502
[2]Patent: EP2679581,2014,A1 .Location in patent: Paragraph 0162
[3]Patent: EP2679582,2014,A1 .Location in patent: Paragraph 0110

41
[ 615-42-9 ]
[ 120-80-9 ]
[ 262-12-4 ]

Yield	Reaction Conditions	Operation in experiment
18%	With copper(l) iodide; iron(III)-acetylacetonate; potassium carbonate In dimethyl sulfoxide at 110℃; for 168h; Inert atmosphere;	General procedure: Typical procedure for the biarylation of diphenols using diiodoarenes or dibromoarenes (3a-3l, 5a-5i): 1,4-diiodobenzene (0.330 g, 1.0 mmol), compound 2a (0.294 g, 1 mmol), K2CO3 (0.552 g, 4.0 mmol), CuI (19.0 mg, 10 mol %), Fe(acac)3 (35.3 mg, 10 mol %) were dissolved in DMSO (anhydrous, 100 mL). The solution was stirred at 110 °C under nitrogen atmosphere for 7 d. When the reaction was cool, the mixture was filtered off, and washed with CH2Cl2 (200 mL). The solution was washed with NaOH (1 mol/L, 200 mL×3) and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/CH2Cl2, 20:1 to 4:1) to give the desired product 3a (177.4 mg, 48.2%) as a white solid.

Reference： [1]Zhou, Qizhong; Su, Liangjun; Jiang, Tiansheng; Zhang, Bin; Chen, Rener; Jiang, Huajiang; Ye, Yuyuan; Zhu, Mengqing; Han, Deman; Shen, Jianfen; Dai, Guoliang; Li, Zhanting [Tetrahedron, 2014, vol. 70, # 6, p. 1125 - 1132]

42
[ 2150-43-8 ]
[ 615-42-9 ]
[ 17054-76-1 ]

Yield	Reaction Conditions	Operation in experiment
16%	With copper(l) iodide; iron(III)-acetylacetonate; potassium carbonate In dimethyl sulfoxide at 110℃; for 168h; Inert atmosphere;	General procedure: Typical procedure for the biarylation of diphenols using diiodoarenes or dibromoarenes (3a-3l, 5a-5i): 1,4-diiodobenzene (0.330 g, 1.0 mmol), compound 2a (0.294 g, 1 mmol), K2CO3 (0.552 g, 4.0 mmol), CuI (19.0 mg, 10 mol %), Fe(acac)3 (35.3 mg, 10 mol %) were dissolved in DMSO (anhydrous, 100 mL). The solution was stirred at 110 °C under nitrogen atmosphere for 7 d. When the reaction was cool, the mixture was filtered off, and washed with CH2Cl2 (200 mL). The solution was washed with NaOH (1 mol/L, 200 mL×3) and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/CH2Cl2, 20:1 to 4:1) to give the desired product 3a (177.4 mg, 48.2%) as a white solid.

Reference： [1]Zhou, Qizhong; Su, Liangjun; Jiang, Tiansheng; Zhang, Bin; Chen, Rener; Jiang, Huajiang; Ye, Yuyuan; Zhu, Mengqing; Han, Deman; Shen, Jianfen; Dai, Guoliang; Li, Zhanting [Tetrahedron, 2014, vol. 70, # 6, p. 1125 - 1132]

43
[ 615-42-9 ]
[ 201230-82-2 ]
[ 1003-03-8 ]
[ 53291-79-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	With triethylamine In toluene at 100℃; for 6h; Autoclave;	General procedure carbonylative cyclization ofmethyl-2-iodobenoate/1,2-diiodo benzene for the synthesis ofN-substituted isoindole-1,3-diones using ImmPd-IL as a catalyst General procedure: General procedure carbonylative cyclization ofmethyl-2-iodobenoate/1,2-diiodo benzene for the synthesis ofN-substituted isoindole-1,3-diones using ImmPd-IL as a catalystIn a 100 mL stainless steel autoclave, methyl-2-iodobenoate/1,2-diiodobenzene (1 mmol), aryl amine (2 mmol), ImmPd-IL(2 mol%), toluene (10 mL) and Et3N (2.5 mmol) were added. Theautoclave was closed, purged three times with nitrogen followedwith carbon monoxide, and then pressurized with 1 atm of CO andheated at 100C for 6 h. After completion of reaction the reac-tor was cooled to room temperature, the remaining CO gas wascarefully vented, and the reactor was opened. The reactor vesselwas thoroughly washed with ethyl acetate (10-15 mL) to removeany traces of product and catalyst if present. The catalyst was fil-tered and the reaction mixture was evaporated under vacuum. Theresidue obtained was purified by column chromatography (silicagel, 60-120 mesh; petroleum ether/ethyl acetate, 95:05) to affordthe desired product. The products were confirmed by GC, GC-MS,1H NMR and13C NMR spectroscopic techniques. The purity of com-pounds was determined by GC-MS analysis.

Reference： [1]Khedkar, Mayur V.; Shinde, Ajinkya R.; Sasaki, Takehiko; Bhanage, Bhalchandra M. [Journal of Molecular Catalysis A: Chemical, 2014, vol. 385, p. 91 - 97]

44
[ 615-42-9 ]
[ 201230-82-2 ]
[ 3218-02-8 ]
[ 41763-91-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	With triethylamine In toluene at 100℃; for 6h; Autoclave;	General procedure carbonylative cyclization ofmethyl-2-iodobenoate/1,2-diiodo benzene for the synthesis ofN-substituted isoindole-1,3-diones using ImmPd-IL as a catalyst General procedure: General procedure carbonylative cyclization ofmethyl-2-iodobenoate/1,2-diiodo benzene for the synthesis ofN-substituted isoindole-1,3-diones using ImmPd-IL as a catalystIn a 100 mL stainless steel autoclave, methyl-2-iodobenoate/1,2-diiodobenzene (1 mmol), aryl amine (2 mmol), ImmPd-IL(2 mol%), toluene (10 mL) and Et3N (2.5 mmol) were added. Theautoclave was closed, purged three times with nitrogen followedwith carbon monoxide, and then pressurized with 1 atm of CO andheated at 100C for 6 h. After completion of reaction the reac-tor was cooled to room temperature, the remaining CO gas wascarefully vented, and the reactor was opened. The reactor vesselwas thoroughly washed with ethyl acetate (10-15 mL) to removeany traces of product and catalyst if present. The catalyst was fil-tered and the reaction mixture was evaporated under vacuum. Theresidue obtained was purified by column chromatography (silicagel, 60-120 mesh; petroleum ether/ethyl acetate, 95:05) to affordthe desired product. The products were confirmed by GC, GC-MS,1H NMR and13C NMR spectroscopic techniques. The purity of com-pounds was determined by GC-MS analysis.

Reference： [1]Khedkar, Mayur V.; Shinde, Ajinkya R.; Sasaki, Takehiko; Bhanage, Bhalchandra M. [Journal of Molecular Catalysis A: Chemical, 2014, vol. 385, p. 91 - 97]

45
[ 615-42-9 ]
[ 149-30-4 ]
[ 1520092-63-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With copper(l) iodide; 1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone; caesium carbonate In dimethyl sulfoxide at 100℃; for 18h; Inert atmosphere;	(Het)aryl Sulfides 3; General Procedure General procedure: Diiodobenzene 1 (0.2 mmol), (het)aryl thiol 2 (0.3 mmol), CuI (0.04mmol), ligand L1 (0.04 mmol), and Cs2CO3 (0.4 mmol) were added to DMSO (1 mL) in a 25-mL round-bottomed flask equipped witha stirring bar. The mixture was stirred at 100 °C for 18 h under N2 then cooled to r.t. H2O (8 mL) was added and the resulting residue was extracted with EtOAc (3 × 8 mL). The organic layers were combined, dried (MgSO4), and concentrated under reduced pressure.The residue was purified by silica flash column chromatography (petroleum ether).
52%	With 1-(4-nitrophenyl)-3-N,N-dimethylamino-2-propen-1-one; copper(II) acetate monohydrate; caesium carbonate In dimethyl sulfoxide at 100℃; for 12h;

Reference： [1]Liu, Yunyun; Wang, Hang; Cao, Xiaoji; Fang, Zheng; Wan, Jie-Ping [Synthesis, 2013, vol. 45, # 21, p. 2977 - 2982]
[2]Liu, Yunyun; Huang, Bin; Cao, Xiaoji; Wu, Dan; Wan, Jie-Ping [RSC Advances, 2014, vol. 4, # 71, p. 37733 - 37737]

46
[ 615-42-9 ]
[ 106-45-6 ]
o-Iodophenyl p-tolyl sulfide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: para-thiocresol With sodium hydride In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 0.0333333h; Stage #2: 1,2-Diiodobenzene In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 3h;	Synthesis example General procedure: At room temperature, NaH (0.9 mmol, 3.0 equiv) was weighed into a reaction flask, suspended in anhydrous THF (0.8 mL) with conventional magnetic stirring, and thiophenol 1 (0.3 mmol, 1.0 equiv) was added dropwise during stirring. Dissolve in 0.2 mL DMA), stir at room temperature for 2 min after the addition, and then add 1,2-diiodobenzene 2a (0.6 mmol, 2.0 equiv, dissolved in 0.2 mL THF), continue to stir at room temperature, and monitor the reaction by TLC. After the completion of the reaction, ice water and tetrahydrofuran were added to quench the reaction, extracted three times with ethyl acetate, the organic layers were combined, washed with saturated NaCl solution, dried over anhydrous sodium sulfate, filtered, and the solvent was spin-dried. Analysis and separation to obtain a product containing iodophenyl sulfide 3, and the yield is routinely calculated.
83%	With copper(l) iodide; 1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone; caesium carbonate In dimethyl sulfoxide at 100℃; for 18h; Inert atmosphere;	(Het)aryl Sulfides 3; General Procedure General procedure: Diiodobenzene 1 (0.2 mmol), (het)aryl thiol 2 (0.3 mmol), CuI (0.04mmol), ligand L1 (0.04 mmol), and Cs2CO3 (0.4 mmol) were added to DMSO (1 mL) in a 25-mL round-bottomed flask equipped witha stirring bar. The mixture was stirred at 100 °C for 18 h under N2 then cooled to r.t. H2O (8 mL) was added and the resulting residue was extracted with EtOAc (3 × 8 mL). The organic layers were combined, dried (MgSO4), and concentrated under reduced pressure.The residue was purified by silica flash column chromatography (petroleum ether).
78%	With sodium hydride In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 3h;	1 Example one General procedure: At room temperature, weigh NaH (0.9 mmol, 3.0 equiv) into the reaction flask,Suspended in anhydrous THF (0.8 mL) with conventional magnetic stirring. During the stirring, thiophenol 1 (0.3 mmol, 1.0 equiv,Dissolve in 0.2 mL DMA), stir at room temperature for 2 min after addition, then add diiodobenzene 2 (0.6 mmol, 2.0 equiv, dissolved in 0.2 mL THF), continue to stir at room temperature,TLC monitors the reaction. After the reaction is complete, add ice water and tetrahydrofuran to quench the reaction, extract 3 times with ethyl acetate, combine the organic layers, wash with saturated NaCl solution, dry with anhydrous sodium sulfate, filter, spin-dry the solvent, add silica gel powder and mix the sample, fast column layer After analysis and separation, the product o-iodophenyl sulfide 3 is obtained, and the yield is conventionally calculated.

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN113651738, 2021, A Location in patent: Paragraph 0018-0020; 0022
[2]Liu, Yunyun; Wang, Hang; Cao, Xiaoji; Fang, Zheng; Wan, Jie-Ping [Synthesis, 2013, vol. 45, # 21, p. 2977 - 2982]
[3]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN113620848, 2021, A Location in patent: Paragraph 0014-0016; 0028

47
[ 615-42-9 ]
[ 106-53-6 ]
4-bromophenyl 2-iodophenyl sulfide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium hydride In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 10h;	1; 3 Example one General procedure: At room temperature, weigh NaH (0.9 mmol, 3.0 equiv) into the reaction flask,Suspended in anhydrous THF (0.8 mL) with conventional magnetic stirring. During the stirring, thiophenol 1 (0.3 mmol, 1.0 equiv,Dissolve in 0.2 mL DMA), stir at room temperature for 2 min after addition, then add diiodobenzene 2 (0.6 mmol, 2.0 equiv, dissolved in 0.2 mL THF), continue to stir at room temperature,TLC monitors the reaction. After the reaction is complete, add ice water and tetrahydrofuran to quench the reaction, extract 3 times with ethyl acetate, combine the organic layers, wash with saturated NaCl solution, dry with anhydrous sodium sulfate, filter, spin-dry the solvent, add silica gel powder and mix the sample, fast column layer After analysis and separation, the product o-iodophenyl sulfide 3 is obtained, and the yield is conventionally calculated.
93%	Stage #1: para-bromobenzenethiol With sodium hydride In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 0.0333333h; Stage #2: 1,2-Diiodobenzene In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 10h;	Synthesis example General procedure: At room temperature, NaH (0.9 mmol, 3.0 equiv) was weighed into a reaction flask, suspended in anhydrous THF (0.8 mL) with conventional magnetic stirring, and thiophenol 1 (0.3 mmol, 1.0 equiv) was added dropwise during stirring. Dissolve in 0.2 mL DMA), stir at room temperature for 2 min after the addition, and then add 1,2-diiodobenzene 2a (0.6 mmol, 2.0 equiv, dissolved in 0.2 mL THF), continue to stir at room temperature, and monitor the reaction by TLC. After the completion of the reaction, ice water and tetrahydrofuran were added to quench the reaction, extracted three times with ethyl acetate, the organic layers were combined, washed with saturated NaCl solution, dried over anhydrous sodium sulfate, filtered, and the solvent was spin-dried. Analysis and separation to obtain a product containing iodophenyl sulfide 3, and the yield is routinely calculated.
76%	With copper(l) iodide; 1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone; caesium carbonate In dimethyl sulfoxide at 100℃; for 18h; Inert atmosphere;	(Het)aryl Sulfides 3; General Procedure General procedure: Diiodobenzene 1 (0.2 mmol), (het)aryl thiol 2 (0.3 mmol), CuI (0.04mmol), ligand L1 (0.04 mmol), and Cs2CO3 (0.4 mmol) were added to DMSO (1 mL) in a 25-mL round-bottomed flask equipped witha stirring bar. The mixture was stirred at 100 °C for 18 h under N2 then cooled to r.t. H2O (8 mL) was added and the resulting residue was extracted with EtOAc (3 × 8 mL). The organic layers were combined, dried (MgSO4), and concentrated under reduced pressure.The residue was purified by silica flash column chromatography (petroleum ether).

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN113620848, 2021, A Location in patent: Paragraph 0014-0016; 0021; 0041
[2]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN113651738, 2021, A Location in patent: Paragraph 0018-0020
[3]Liu, Yunyun; Wang, Hang; Cao, Xiaoji; Fang, Zheng; Wan, Jie-Ping [Synthesis, 2013, vol. 45, # 21, p. 2977 - 2982]

48
[ 112-34-5 ]
[ 615-42-9 ]
[ 71784-20-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 40h; Reflux; Inert atmosphere;	5 Example 5 Synthesis of 1 2-bis(2-(2-(butyloxy)ethoxy)ethoxy)benzene [00136] Copper (I) iodide (FW 190.45, 1.80 grams, 9.50 mmol), 1,10-phenanthroline ((FW 180.23, 1.71 grams, 9.50 mmol), cesium carbonate ((FW 325.82, 38.00 grams, 1 16.60 mmol), 1 ,2-diiodobenzene (FW 329.90, 15.00 grams, 45.50 mmol), di(ethylene glycol) butyl ether (FW 162.23, 22.15 grams, 136.50 mmol) and 100 milliliters of dry xylene were charged in a 500 milliliter round bottom flask. The reaction mixture was heated with stirring at reflex temperature for 40 hours under nitrogen. The resulting suspension was cooled to room temperature and filtered through celite and alumina. The filtrate was concentrated at high vacuum. The residue was purified by flask chromatography on silica gel with 1 : 1 hexane and ethyl acetate. The final dark yellow product was yielded 13.50 grams (75 %). The product 'H NMR analysis shows the formation of aryl ether product. 'H NMR (CDC13): δ 6.89 (m, 4H, Ph), 4.17 (t, 4H, -OCH2-), 3.87 (m, 4H, -CH2O-) 3.72 (m, 4H, -OCH2), 3.59(m, 4H, -CH2O-,), 3.46(t, 4H, -OCH2-), 1.43-1.13 (m 4H, -CH2-), 0.91 (t, 6H, -CH3).
4 g	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 24h; Inert atmosphere;	5 Synthesis of 1,2-bis(2-(2-butoxy)ethoxy)ethoxy)benzene Example 5 Synthesis of 1,2-bis(2-(2-butoxy)ethoxy)ethoxy)benzene 1,2-diiodobenzene (5 g, 0.0152 mol, MW:329.91), di(ethylene glycol)butyl ether (9.83 g, 0.0606 mol, MW:162.23), cesium carbonate, (12.44 g, 0.0379 mol, MW:328.5), 1,10-phenathroline (0.546 g, 0.00303 mol, MW:180.21), copper (I) iodide (0.0.60 g, 0.0030 mol, MW:195.01) and 50 ml of dry xylene were charged in 350 ml three necked round bottom flask. The reaction mixture was heated with stirring at 140° C. for 24 hours under nitrogen. The resulting suspension was cooled to room temperature and filtered through celite. The filtrate was concentrated at 180° C. under high vacuum. The residue was purified by flask chromatography on silica gel with hexane. The yield of the final pale-yellow product was 4.0 grams. The product 13C NMR analysis suggests the formation of 1,2-diarylether glycol ether product. 13C NMR (CDCl3): 149.19, 121.89, 115.13, 71.14, 70.87, 70.16, 69.79, 68.95, 31.62, 19.46, 13.78

Reference： [1]Current Patent Assignee: EXXON MOBIL CORP - WO2015/60985, 2015, A1 Location in patent: Paragraph 00136
[2]Current Patent Assignee: EXXON MOBIL CORP - US2020/377450, 2020, A1 Location in patent: Paragraph 0077; 0078

49
[ 111-90-0 ]
[ 615-42-9 ]
[ 57721-94-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In 5,5-dimethyl-1,3-cyclohexadiene; for 20h;Reflux; Inert atmosphere;	[00150] Copper (I) iodide (FW 190.45, 0.90 grams, 4.72 mmol), 1,10-phenanthroline (FW 180.21, 0.83 grams, 4.62 mmol), cesium carbonate (FW 325.82, 19.00 grams, 58.30 mmol), 1 ,2-diiodobenzene (FW 329.90, 7.50 grams, 22.70 mol), di(ethylene glycol) ethyl ether (FW 134.17, 9.18 grams, 68.40 mol) and 100 milliliters of dry xylene were charged in a 350 milliliter three necked round bottom flask. The reaction mixture was heated with stirring at reflux temperature for 20 hours under nitrogen. The resulting suspension was cooled to room temperature by adding 50 milliliters of toluene. Then reaction mixture was filtered through celite and alumina. The low boiling (xylene and toluene) component was removed by a rotary evaporator and high boiling component di(ethylene glycol) ethyl ether by air bath oven at 200C under high vacuum for 2 hours. The residue was purified by flask chromatography on silica gel. The final dark yellow product yielded 7.00 grams (90%). The product I and C NMR analysis shows the formation of aryl ether product. IR: neat (cm" FontWeight="Bold" FontSize="10" ): 745, 843, 931, 1052, 1 1 16, 1219, 1256, 1325, 1350, 1373, 1453, 1501, 1593, 2869, 2929, 2973. 1H NMR (CDC13): delta 6.76 (m, 4H, Ph), 4.02 (t, 4H, -OCH2-), 3.71 (m, 4H, -CH2O-) 3.57 (m, 4H, -OCH2), 3.45(m, 4H, -OCH2-), 3.37(t, 4H, -OCH2-), 1.06 (t, 6H, -CH3). 13C NMR (CDC13): 149.42, 121.61, 1 15.04, 70.89, 69.89, 69.76, 68.93, 66.59, 15.14.

Reference： [1]Patent: WO2015/60985,2015,A1 .Location in patent: Paragraph 00150

50
[ 615-42-9 ]
[ 476004-81-6 ]
1,2-bis(1H-indol-2-yl)benzene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 14891 - 14895
Angew. Chem.,2018,vol. 130,p. 15107 - 15111,5
[2]Chemical Communications,2015,vol. 51,p. 8123 - 8125

51
[ 59311-67-0 ]
[ 615-42-9 ]
3-(2-(thiophen-3-yl)ethyl)benzo[d]thiazole-2(3H)-thione [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 34 - 37

52
[ 59311-67-0 ]
[ 615-42-9 ]
C₁₂H₁₂INS [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 34 - 37

53
[ 615-42-9 ]
[ 17985-72-7 ]
[ 33022-24-1 ]

Yield	Reaction Conditions	Operation in experiment
43%Chromat.	With Pd(P(t-Bu)2(4-Me2NC6H4))2; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 20℃; for 24h;	General procedure: 1,2-Diiodoarene, 1,2-bis(dimethylsilyl)arene (1.5 equiv), and N,N-diisopropylethylamine (6.0 equiv) were added to a solution of Pd(P(t-Bu)2(4-Me2NC6H4))2 (0.05 equiv) in 1,2-dichloroethane (0.5M). The reaction progress was monitored by GC or TLC. After the atarting material was consumed at room temperature (1d), the reaction mixture was quenched with water. The aqueous layer was extracted with dichloromethane three times and dried over sodium sulfate. The combined organic layer was analyzed by GC to estimate the yield of product with dodecane as an internal standard. The solvent was removed under reduced pressure and purified roughly by flash column chromatography over silica gel. In the case of 7, the yield was estimated by 1H NMR analysis at this stage. The methyl proton integrals at delta 0.56 vs 0.68 and 0.88ppm can be measured separately and used to determine the ratio of cyclized and non-cyclized products. Analytical pure products were isolated by the purification of crude products with GPC (eluent: CHCl3) and/or recrystallization from methanol. 9,9,10,10-Tetramethyl-9,10-dihydro-9,10-disilaanthracene (1) [4a-c]. GC yield: 43%. Isolated yield of analytically pure compound: 29%. Colorless solid. Eluent for TLC: hexane. 1H NMR (500MHz, CDCl3) delta 7.69 (dd, 4H, J=3.3, 5.5Hz), 7.42 (dd, 4H, J=3.3, 5.5Hz), 0.48 (s, 12H). 13C NMR (125MHz, CDCl3) delta 144.5 (Cq), 133.4 (CH), 128.3 (CH), 0.0 (CH3). EI-MS m/z 268 (M+).

Reference： [1]Journal of Organometallic Chemistry,2016,vol. 805,p. 27 - 33

54
[ 615-42-9 ]
[ 30413-54-8 ]
1,2-bis((4-methylpyridin-2-yl)ethynyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; diethylamine In N,N-dimethyl-formamide at 120℃; for 0.166667h; Inert atmosphere; Microwave irradiation;

Reference： [1]Carlsson, Anna-Carin C.; Mehmeti, Krenare; Uhrbom, Martin; Karim, Alavi; Bedin, Michele; Puttreddy, Rakesh; Kleinmaier, Roland; Neverov, Alexei A.; Nekoueishahraki, Bijan; Gräfenstein, Jürgen; Rissanen, Kari; Erdélyi, Máté [Journal of the American Chemical Society, 2016, vol. 138, # 31, p. 9853 - 9863]

55
[ 615-42-9 ]
[ 30413-54-8 ]
2-[2-(2-iodophenyl)ethynyl]-4-methylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine In N,N-dimethyl-formamide at 120℃; for 0.0833333h; Inert atmosphere; Microwave irradiation;
27%	With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; diethylamine In N,N-dimethyl-formamide at 120℃; for 0.0666667h; Inert atmosphere; Microwave irradiation;

Reference： [1]Lindblad, Sofia; Mehmeti, Krenare; Veiga, Alberte X.; Nekoueishahraki, Bijan; Gräfenstein, Jürgen; Erdélyi, Máté [Journal of the American Chemical Society, 2018, vol. 140, # 41, p. 13503 - 13513]
[2]Carlsson, Anna-Carin C.; Mehmeti, Krenare; Uhrbom, Martin; Karim, Alavi; Bedin, Michele; Puttreddy, Rakesh; Kleinmaier, Roland; Neverov, Alexei A.; Nekoueishahraki, Bijan; Gräfenstein, Jürgen; Rissanen, Kari; Erdélyi, Máté [Journal of the American Chemical Society, 2016, vol. 138, # 31, p. 9853 - 9863]

56
[ 64-18-6 ]
[ 615-42-9 ]
[ 693-13-0 ]
[ 304-17-6 ]

Reference： [1]Chemistry - An Asian Journal,2016,vol. 11,p. 3508 - 3512

57
[ 111-74-0 ]
[ 615-42-9 ]
[ 72119-43-8 ]

Yield	Reaction Conditions	Operation in experiment
21%	With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene at 110℃; for 24h; Schlenk technique; Inert atmosphere;	2. General procedure for the synthesis of quinoxaline derivatives General procedure: An oven-dried Schlenk tube equipped with a Teflon valve was charged with amagnetic stir bar, CuI (0.05 mmol), 1,2-diiodobenzenes or 1,8-diiodonaphthalene a(0.5 mmol) and DBU (1.0 mmol). The tube was placed under vacuum for twentyminutes and backfilled with N2. Then N, N’- disubstituted -1,2-diamines b (1.0 mmol)was added through a syringe. The reaction mixture was stirred at 110 oC for 24 h. Thereaction was monitored by TLC. When 1,2-diiodobenzenes or 1,8-diiodonaphthalenea consumed completely, the reaction was stopped and purified directly by columnchromatography on silica gel to give the pure products c (petroleum ether/EtOAc v/v= 10/1).

Reference： [1]Shen, Guodong; Zhao, Lingyu; Zhao, Xiliang; Huangfu, Xinlei; Li, Zhe; Wang, Rui; Zhang, Tongxin [Synlett, 2017, vol. 28, # 9, p. 1111 - 1115]

58
[ 615-42-9 ]
[ 26066-88-6 ]
C₁₇H₁₀BrIN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); tributylphosphine; sodium t-butanolate; In toluene; for 4h;Inert atmosphere; Reflux;	take 750mmol of raw materials 4, adding 750mmol o-diiodobenzene,1 L of toluene, 2250 mmol of sodium tert-butoxide,7.5 mmol Pd2 (dba) 3 catalyst, 30 mmol tri-tert-butyl phosphorus,Ar gas replacement system three times, reflux temperature reaction overnight,The crude product was passed through a silica gel column to give the product 500 mmol. Product 5.

Reference： [1]Patent: CN106588970,2017,A .Location in patent: Paragraph 0041; 0044

59
[ 615-42-9 ]
[ 602-56-2 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 216 - 219

60
[ 615-42-9 ]
[ 75-07-0 ]
[ 13509-78-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With cobalt(II) chloride hexahydrate; oxygen; acetic acid at 23℃; for 5h; Sealed tube;	General method for the oxidation of iodoarenes. General procedure: In a typical experiment, a 20 ml scintillation vial was charged with glacial AcOH (2 ml), iodoarene (0.401 mmol) andCoCl2·6H2O (0.004 mmol, 1 mol%) and was fitted with a rubber septum. The reaction vessel was purged with O2 for 5 min before acetaldehyde (4.07 mmol, 10.2 equiv.) was added in one portion. The reaction mixture was stirred under 1 atm O2, delivered by inflated balloon at 23 °C for 5 h. The solvent was removed in vacuo and the residuewasdissolved in CH2Cl2. The organic layer was washed with distilled water and extracted with CH2Cl2 (3 × 7 ml). The organic layer was dried over MgSO4 and solvent was removed in vacuo to afford the corresponding iodobenzene diacetate. The isolatedcompounds were characterized by 1H and 13C NMR spectroscopies.
90%	With cobalt(II) chloride hexahydrate; oxygen In acetic acid at 23℃; for 10h;	B1 Synthesis of 1,3-diacetoxy-1,3-dihydro-1,3,2-benzoiodooxole (7) A 20-mL scintillation vial was charged with glacial AcOH (2 mL), 1,2-diiodobenzene (132 mg, 0.400 mmol, 1.00 eq.) and CoCl2.6H2O (0.9 mg, 0.004 mmol, 1 mol %) and was fitted with a rubber septum. The reaction vessel was purged with O2 for 5 min before acetaldehyde (224 μL, 4.07 mmol, 10.0 eq.) was added in one portion. The reaction mixture was stirred under 1 atm O2, delivered by inflated balloon, at 23° C. for 10 h. Solvent was reduced in vacuo and hexanes were added. The observed white precipitate was isolated by filtration, washed with hexanes, and dried in vacuo to afford 167 mg of the title compound (90% yield). 1H NMR (δ, 23° C., CDCl3): 8.03 (dd, J=6.1, 3.4 Hz, 2H), 7.63 (dd, J=6.1, 3.4 Hz, 2H), 2.09 (s, 6H). 13C NMR (δ, 23° C., CDCl3): 178.1, 135.3, 131.9, 21.6.

Reference： [1]Maity, Asim; Hyun, Sung-Min; Powers, David C. [Nature Chemistry, 2018, vol. 10, # 2, p. 200 - 204]
[2]Current Patent Assignee: TEXAS A&M UNIVERSITY SYSTEM - US2019/2487, 2019, A1 Location in patent: Paragraph 0091-0092

61
[ 615-42-9 ]
[ 654664-63-8 ]
2-(2-iodophenyl)triphenylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58.2%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; for 18h;Inert atmosphere; Reflux;	A solution of toluene (450 mL) and ethanol (150 mL) was bubbled with nitrogen gas for 10 min. Triphenylen-2-ylboronic acid (10.0 g g, 36.7 mmol), 1,2-diiodobenzene (36.4 g, 110 mmol), tetrakis(triphenylphosphine)palladium(0) (2.1 g, 1.8 mmol), and tripotassium phosphate (39.0 g, 184 mmol) were added. The mixture was bubbled with nitrogen gas for 15 minutes and refluxed for 18 hours. After cooling (22 C.), the reaction mixture was filtered through a silica pad and washed with toluene. The solvent was removed in vacuo and the residue was purified by flash column chromatography using hexane to 30% DCM in hexane to yield the desired product 2-(2-iodophenyl)triphenylene (9.2 g, 21.4 mmol, 58.2% yield) as a pale yellow solid.

Reference： [1]Patent: US2018/108844,2018,A1 .Location in patent: Paragraph 0129-0130

62
[ 615-42-9 ]
[ 201230-82-2 ]
[ 88-74-4 ]
[ 34442-94-9 ]

Yield	Reaction Conditions	Operation in experiment
48%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained

Reference： [1]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]

63
[ 111-26-2 ]
[ 615-42-9 ]
[ 201230-82-2 ]
[ 20320-48-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained

Reference： [1]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]

64
[ 95-82-9 ]
[ 615-42-9 ]
[ 201230-82-2 ]
[ 1485-35-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained

Reference： [1]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]

65
[ 615-42-9 ]
[ 201230-82-2 ]
[ 634-93-5 ]
[ 1485-34-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained

Reference： [1]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]

66
[ 107-10-8 ]
[ 615-42-9 ]
[ 201230-82-2 ]
[ 5323-50-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained

Reference： [1]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]

67
[ 615-42-9 ]
[ 201230-82-2 ]
[ 615-36-1 ]
[ 19357-21-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained

Reference： [1]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]

68
[ 110-89-4 ]
[ 615-42-9 ]
[ 201230-82-2 ]
[ 100073-02-7 ]
[ 38256-33-6 ]
C₂₀H₂₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 60% 2: 19 %Chromat. 3: 12 %Chromat.	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained.
1: 47% 2: 34 %Chromat. 3: 19 %Chromat.	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained.
1: 35 %Chromat. 2: 34% 3: 25 %Chromat.	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained.

1: 70 %Chromat. 2: 18 %Chromat. 3: 12 %Chromat.

With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;

General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained.

Reference： [1]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]
[2]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]
[3]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]
[4]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]

69
[ 110-91-8 ]
[ 615-42-9 ]
[ 201230-82-2 ]
[ 6425-65-6 ]
[ 1346236-09-6 ]
N,N-(3-oxa-pentane-1,5-diyl)-2-iodobenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 75% 2: 7 %Chromat. 3: 10 %Chromat.	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained.

Reference： [1]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]

70
[ 123-75-1 ]
[ 615-42-9 ]
[ 201230-82-2 ]
C₁₆H₂₀N₂O₂ [ No CAS ]
C₁₈H₂₀N₂O₄ [ No CAS ]
N-(o-iodobenzoyl)pyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 53% 2: 20 %Chromat. 3: 13 %Chromat.	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained.
1: 45% 2: 45 %Chromat. 3: 8 %Chromat.	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained.
1: 24% 2: 54 %Chromat. 3: 11 %Chromat.	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained.

1: 71%Chromat. 2: 11 %Chromat. 3: 8%

With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;

General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained.

Reference： [1]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]
[2]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]
[3]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]
[4]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]

71
[ 109-97-7 ]
[ 615-42-9 ]
[ 201230-82-2 ]
C₁₆H₁₂N₂O₂ [ No CAS ]
[ 130259-66-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 81% 2: 8 %Chromat.	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained.
1: 73% 2: 8 %Chromat.	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Schlenk technique;	General procedure for aminocarbonylation General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 °C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained.

Reference： [1]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]
[2]Wójcik, Przemysław; Trzeciak, Anna M. [Applied Catalysis A: General, 2018, vol. 560, p. 73 - 83]

72
[ 615-42-9 ]
[ 108-18-9 ]
[ 4107-98-6 ]

Yield	Reaction Conditions	Operation in experiment
35%	In n-heptane;Inert atmosphere; UV-irradiation;	General procedure: Under an N2 atmosphere, substrate 1 (0.2 mmol) and 1,2-diiodobenzene(IV) (0.1 mmol) were placed in a dry glass tube. Heptane (10 mL)was added and the well-stirred mixture was irradiated under UV light(300 nm) until the reaction was complete (TLC monitoring). The solvent was removed in vacuo and the residue was purified by silica gel column chromatography to afford the coupling product 2.

Reference： [1]Synthesis,2018,vol. 50,p. 2981 - 2989

73
[ 110-91-8 ]
[ 615-42-9 ]
[ 92-53-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	In n-heptane;Inert atmosphere; UV-irradiation;	General procedure: Under an N2 atmosphere, substrate 1 (0.2 mmol) and 1,2-diiodobenzene(IV) (0.1 mmol) were placed in a dry glass tube. Heptane (10 mL)was added and the well-stirred mixture was irradiated under UV light(300 nm) until the reaction was complete (TLC monitoring). The solvent was removed in vacuo and the residue was purified by silica gel column chromatography to afford the coupling product 2.

Reference： [1]Synthesis,2018,vol. 50,p. 2981 - 2989

74
[ 589-09-3 ]
[ 615-42-9 ]
[ 3998-04-7 ]

Yield	Reaction Conditions	Operation in experiment
24%	In n-heptane Inert atmosphere; UV-irradiation;	Carbazoles 4; General Procedure General procedure: Under an N2 atmosphere, substrate 3 (0.2 mmol) and 1,2-diiodobenzene(IV) (0.1 mmol) were placed in a dry glass tube. Heptane (10 mL) was added and the well-stirred mixture was irradiated under UV light(300 nm) until the reaction was complete (TLC monitoring). The solvent was removed in vacuo and the residue was purified by silica gelcolumn chromatography to afford the corresponding carbazole 4.

Reference： [1]Zhao, Xinxin; Chen, Ming; Huang, Binbin; Yang, Chao; Gao, Yuan; Xia, Wujiong [Synthesis, 2018, vol. 50, # 15, p. 2981 - 2989]

75
[ 615-42-9 ]
[ 758640-21-0 ]
[ 19402-87-0 ]

Yield	Reaction Conditions	Operation in experiment
42%	In n-heptane;Inert atmosphere; UV-irradiation;	General procedure: Under an N2 atmosphere, substrate 3 (0.2 mmol) and 1,2-diiodobenzene(IV) (0.1 mmol) were placed in a dry glass tube. Heptane (10 mL) was added and the well-stirred mixture was irradiated under UV light(300 nm) until the reaction was complete (TLC monitoring). The solvent was removed in vacuo and the residue was purified by silica gelcolumn chromatography to afford the corresponding carbazole 4.

Reference： [1]Synthesis,2018,vol. 50,p. 2981 - 2989

76
[ 615-42-9 ]
[ 4714-62-9 ]
[ 91828-10-3 ]

Yield	Reaction Conditions	Operation in experiment
23%	In n-heptane;Inert atmosphere; UV-irradiation;	General procedure: Under an N2 atmosphere, substrate 3 (0.2 mmol) and 1,2-diiodobenzene(IV) (0.1 mmol) were placed in a dry glass tube. Heptane (10 mL) was added and the well-stirred mixture was irradiated under UV light(300 nm) until the reaction was complete (TLC monitoring). The solvent was removed in vacuo and the residue was purified by silica gelcolumn chromatography to afford the corresponding carbazole 4.

Reference： [1]Synthesis,2018,vol. 50,p. 2981 - 2989

77
[ 615-42-9 ]
[ 22864-65-9 ]
9-methyl-3-(trifluoromethyl)-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	In n-heptane;Inert atmosphere; UV-irradiation;	General procedure: Under an N2 atmosphere, substrate 3 (0.2 mmol) and 1,2-diiodobenzene(IV) (0.1 mmol) were placed in a dry glass tube. Heptane (10 mL) was added and the well-stirred mixture was irradiated under UV light(300 nm) until the reaction was complete (TLC monitoring). The solvent was removed in vacuo and the residue was purified by silica gelcolumn chromatography to afford the corresponding carbazole 4.

Reference： [1]Synthesis,2018,vol. 50,p. 2981 - 2989

78
[ 615-42-9 ]
[ 177171-16-3 ]
[ 95918-90-4 ]

Reference： [1]Patent: JP6126577,2017,B2

79
[ 615-42-9 ]
[ 33577-99-0 ]
methyl 2-((2-iodophenyl)ethynyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-butylamine; In diethyl ether; at 20℃; for 6h;	To a stirred solution of 1,2-diiodobenzene (4.95 g, 15 mmol) in Et2O (100 mL) containing Pd(PPh3)4 (0.75 g, 0.625 mmol) was added methyl 2-ethynylbenzoate (2) (2.0 g, 12.5 mmol), CuI (0.24 g, 1.0 mmol) and n-BuNH2 (1.83 g, 12.3 mmol). The resulting solution was stirred at room temperature for 6 h, quenched by saturated aqueous NH4Cl (100 mL), and extracted by EtOAc (100 mL 2). The combined organic layers were dried over MgSO4. After filtration and removal of EtOAc, the residue was purified by column chromatography on silica gel to give methyl 2-((2-iodophenyl)ethynyl)benzoate (3) (3.7 g. 82%).

Reference： [1]Tetrahedron,2019,vol. 75,p. 1034 - 1043

80
[ 21109-25-1 ]
[ 615-42-9 ]
[ 205-32-3 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 8101 - 8105

81
[ 615-42-9 ]
[ 573-97-7 ]
1-bromo-2-(2-iodophenoxy)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: 1-bromo-2-naphthol With sodium hydride In tetrahydrofuran; N,N-dimethyl acetamide; mineral oil at 20℃; for 0.166667h; Stage #2: 1,2-Diiodobenzene In tetrahydrofuran; N,N-dimethyl acetamide; mineral oil at 20℃; for 1h;	6 Example 6 Suspend sodium hydride (60% in oil, 36 mg, 0.9 mmol, 3 eq.) in THF (1 mL), add phenol 2e (38 mg, 0.3 mmol, 1 eq.) under regular stirring and add phenol 2e (38 mg, 0.3 mmol, 1 eq.) in DMA (0.3 mL After adding the solution in ), stir at room temperature for 10 minutes, then add a solution of 1a (148 mg, 0.45 mmol, 1.5 eq.) in THF (0.2 mL), react at room temperature for 1 hour, quench with water, and use ethyl acetate The ester was extracted three times, the organic layers were combined, dried with sodium sulfate, evaporated to dryness, and purified by column chromatography to obtain the product iodo aromatic ether 3ae with a yield of 91%.

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN112979400, 2021, A Location in patent: Page/Page column 6

82
[ 615-42-9 ]
[ 26767-16-8 ]
[ 98-80-6 ]
[ 68089-73-6 ]

Reference： [1]Organic Letters,2021,vol. 23,p. 7150 - 7155

83
[ 615-42-9 ]
[ 2557-78-0 ]
1,2-bis((2-fluorophenyl)thio)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With copper dichloride; N,N`-dimethylethylenediamine at 110℃; for 24h; Inert atmosphere; Green chemistry;	General procedure for the synthesis of diphenylsulfanes by iodobenzenes and benzenethiols (2c-29c). General procedure: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, CuCl2 (15 mol%), iodobenzenes a (0.3 mmol) and benzenethiols d (0.3 mmol). The tube was placed under vacuum for 20 min and backfilled with N2. Then DMEDA (0.35 mL) was added through a syringe. The reaction mixture was stirred at 110 °C for 24 h. The reaction was monitored by TLC. When iodobenzenes a was consumed completely, the reaction was stopped and cooled to room temperature, the crude reaction mixture was filtered through the filter paper with EtOAc (20 mL) for 3 times. The combined organic phase was washed with water (30mL × 3), then concentrated and the residue was purified directly by column chromatography on silica gel using petrol/EtOAc as eluent to give the pure products c.

Reference： [1]Shen, Guodong; Lu, Qichao; Wang, Zeyou; Sun, Weiwei; Zhang, Yalin; Huang, Xianqiang; Sun, Manman; Wang, Zhiming [Synthesis, 2022, vol. 54, # 1, p. 184 - 198]

84
[ 615-42-9 ]
[ 2557-78-0 ]
[ 908242-65-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydride In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 10h;	1; 2 Example one General procedure: At room temperature, weigh NaH (0.9 mmol, 3.0 equiv) into the reaction flask,Suspended in anhydrous THF (0.8 mL) with conventional magnetic stirring. During the stirring, thiophenol 1 (0.3 mmol, 1.0 equiv,Dissolve in 0.2 mL DMA), stir at room temperature for 2 min after addition, then add diiodobenzene 2 (0.6 mmol, 2.0 equiv, dissolved in 0.2 mL THF), continue to stir at room temperature,TLC monitors the reaction. After the reaction is complete, add ice water and tetrahydrofuran to quench the reaction, extract 3 times with ethyl acetate, combine the organic layers, wash with saturated NaCl solution, dry with anhydrous sodium sulfate, filter, spin-dry the solvent, add silica gel powder and mix the sample, fast column layer After analysis and separation, the product o-iodophenyl sulfide 3 is obtained, and the yield is conventionally calculated.
78%	Stage #1: 2-fluorothiophenol With sodium hydride In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 0.0333333h; Stage #2: 1,2-Diiodobenzene In tetrahydrofuran; N,N-dimethyl acetamide at 20℃;	At room temperature, NaH (0.9 mmol, 3.0 equiv) was weighed into a reaction flask, suspended in anhydrous THF (0.8 mL) with conventional magnetic stirring, and thiophenol 1a (0.3 mmol, 1.0 equiv, Dissolve in 0.2 mL DMA), stir at room temperature for 2 min after the addition, and then add 1,2-diiodobenzene 2a (0.6 mmol, 2.0 equiv, dissolved in 0.2 mL THF), continue to stir at room temperature, and monitor the reaction by TLC. After the completion of the reaction, ice water and tetrahydrofuran were added to quench the reaction, extracted three times with ethyl acetate, the organic layers were combined, washed with saturated NaCl solution, dried over anhydrous sodium sulfate, filtered, and the solvent was spin-dried. Analysis and separation to obtain the product containing iodophenyl sulfide 3a, and the conventional calculation yield is 78%.

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN113620848, 2021, A Location in patent: Paragraph 0014-0016; 0037-0039
[2]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN113651738, 2021, A Location in patent: Paragraph 0025-0027

85
[ 615-42-9 ]
[ 937-00-8 ]
C₁₃H₈F₃IS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: 3-trifluoromethyl-thiophenol With sodium hydride In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 0.0333333h; Stage #2: 1,2-Diiodobenzene In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 1h;	Synthesis example General procedure: At room temperature, NaH (0.9 mmol, 3.0 equiv) was weighed into a reaction flask, suspended in anhydrous THF (0.8 mL) with conventional magnetic stirring, and thiophenol 1 (0.3 mmol, 1.0 equiv) was added dropwise during stirring. Dissolve in 0.2 mL DMA), stir at room temperature for 2 min after the addition, and then add 1,2-diiodobenzene 2a (0.6 mmol, 2.0 equiv, dissolved in 0.2 mL THF), continue to stir at room temperature, and monitor the reaction by TLC. After the completion of the reaction, ice water and tetrahydrofuran were added to quench the reaction, extracted three times with ethyl acetate, the organic layers were combined, washed with saturated NaCl solution, dried over anhydrous sodium sulfate, filtered, and the solvent was spin-dried. Analysis and separation to obtain a product containing iodophenyl sulfide 3, and the yield is routinely calculated.
78%	With sodium hydride In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 1h;	1 Example one General procedure: At room temperature, weigh NaH (0.9 mmol, 3.0 equiv) into the reaction flask,Suspended in anhydrous THF (0.8 mL) with conventional magnetic stirring. During the stirring, thiophenol 1 (0.3 mmol, 1.0 equiv,Dissolve in 0.2 mL DMA), stir at room temperature for 2 min after addition, then add diiodobenzene 2 (0.6 mmol, 2.0 equiv, dissolved in 0.2 mL THF), continue to stir at room temperature,TLC monitors the reaction. After the reaction is complete, add ice water and tetrahydrofuran to quench the reaction, extract 3 times with ethyl acetate, combine the organic layers, wash with saturated NaCl solution, dry with anhydrous sodium sulfate, filter, spin-dry the solvent, add silica gel powder and mix the sample, fast column layer After analysis and separation, the product o-iodophenyl sulfide 3 is obtained, and the yield is conventionally calculated.

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN113651738, 2021, A Location in patent: Paragraph 0018-0020
[2]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN113620848, 2021, A Location in patent: Paragraph 0014-0016; 0025

86
[ 615-42-9 ]
[ 36801-01-1 ]
C₁₃H₈INS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: 4-cyanobenzenethiol With sodium hydride In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 0.0333333h; Stage #2: 1,2-Diiodobenzene In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 2h;	Synthesis example General procedure: At room temperature, NaH (0.9 mmol, 3.0 equiv) was weighed into a reaction flask, suspended in anhydrous THF (0.8 mL) with conventional magnetic stirring, and thiophenol 1 (0.3 mmol, 1.0 equiv) was added dropwise during stirring. Dissolve in 0.2 mL DMA), stir at room temperature for 2 min after the addition, and then add 1,2-diiodobenzene 2a (0.6 mmol, 2.0 equiv, dissolved in 0.2 mL THF), continue to stir at room temperature, and monitor the reaction by TLC. After the completion of the reaction, ice water and tetrahydrofuran were added to quench the reaction, extracted three times with ethyl acetate, the organic layers were combined, washed with saturated NaCl solution, dried over anhydrous sodium sulfate, filtered, and the solvent was spin-dried. Analysis and separation to obtain a product containing iodophenyl sulfide 3, and the yield is routinely calculated.
78%	With sodium hydride In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 2h;	1 Example one General procedure: At room temperature, weigh NaH (0.9 mmol, 3.0 equiv) into the reaction flask,Suspended in anhydrous THF (0.8 mL) with conventional magnetic stirring. During the stirring, thiophenol 1 (0.3 mmol, 1.0 equiv,Dissolve in 0.2 mL DMA), stir at room temperature for 2 min after addition, then add diiodobenzene 2 (0.6 mmol, 2.0 equiv, dissolved in 0.2 mL THF), continue to stir at room temperature,TLC monitors the reaction. After the reaction is complete, add ice water and tetrahydrofuran to quench the reaction, extract 3 times with ethyl acetate, combine the organic layers, wash with saturated NaCl solution, dry with anhydrous sodium sulfate, filter, spin-dry the solvent, add silica gel powder and mix the sample, fast column layer After analysis and separation, the product o-iodophenyl sulfide 3 is obtained, and the yield is conventionally calculated.

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN113651738, 2021, A Location in patent: Paragraph 0018-0020
[2]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN113620848, 2021, A Location in patent: Paragraph 0014-0016; 0026

87
[ 615-42-9 ]
[ 700-96-9 ]
C₁₄H₁₃IO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydride; In tetrahydrofuran; N,N-dimethyl acetamide; at 40℃; for 2h;	General procedure: At room temperature, weigh NaH (0.9 mmol, 3.0 equiv) into the reaction flask,Suspended in anhydrous THF (0.8 mL) with conventional magnetic stirring. During the stirring, thiophenol 1 (0.3 mmol, 1.0 equiv,Dissolve in 0.2 mL DMA), stir at room temperature for 2 min after addition, then add diiodobenzene 2 (0.6 mmol, 2.0 equiv, dissolved in 0.2 mL THF), continue to stir at room temperature,TLC monitors the reaction. After the reaction is complete, add ice water and tetrahydrofuran to quench the reaction, extract 3 times with ethyl acetate, combine the organic layers, wash with saturated NaCl solution, dry with anhydrous sodium sulfate, filter, spin-dry the solvent, add silica gel powder and mix the sample, fast column layer After analysis and separation, the product o-iodophenyl sulfide 3 is obtained, and the yield is conventionally calculated.

Reference： [1]Patent: CN113620848,2021,A .Location in patent: Paragraph 0014-0016

88
[ 615-42-9 ]
[ 76041-72-0 ]
C₁₂H₇F₃INS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	Stage #1: 2-mercapto-5-trifluoromethylpyridine With sodium hydride In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 0.05h; Stage #2: 1,2-Diiodobenzene In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 3h;	1 Example 1 General procedure: At room temperature, NaH (1.2 mmol, 4.0 equiv) was weighed into a reaction flask, suspended in anhydrous THF (0.8 mL) and stirred magnetically. During the stirring process, heterocyclic thiophenol 1 (0.3 mmol, 1.0 equiv, Dissolve in 0.2 mL DMA), stir at room temperature for 3 min after addition, then add diiodobenzene 2a (0.6 mmol, 2.0 equiv, dissolved in 0.2 mL THF), continue to stir at room temperature, and monitor the reaction by TLC. After the completion of the reaction, ice water and tetrahydrofuran were added to quench the reaction, extracted three times with ethyl acetate, the organic layers were combined, washed with saturated NaCl solution, dried over anhydrous sodium sulfate, filtered, and the solvent was spin-dried. Analysis and separation to obtain heterocyclic o-iodo sulfide product 3, and the yield is conventionally calculated.

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN113683559, 2021, A Location in patent: Paragraph 0014

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CAS No. :	615-42-9	MDL No. :	MFCD00001038
Formula :	C₆H₄I₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BBOLNFYSRZVALD-UHFFFAOYSA-N
M.W :	329.91	Pubchem ID :	11994
Synonyms :

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	51.88
TPSA :	0.0 Å²

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.03 cm/s

Log Po/w (iLOGP) :	2.25
Log Po/w (XLOGP3) :	3.22
Log Po/w (WLOGP) :	2.9
Log Po/w (MLOGP) :	4.1
Log Po/w (SILICOS-IT) :	3.83
Consensus Log Po/w :	3.26

[ CAS No. 615-42-9 ] {[proInfo.proName]}

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Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-4.47
Solubility :	0.0112 mg/ml ; 0.000034 mol/l
Class :	Moderately soluble
Log S (Ali) :	-2.89
Solubility :	0.422 mg/ml ; 0.00128 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.27
Solubility :	0.0177 mg/ml ; 0.0000537 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.14

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
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P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
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P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
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Response
Code	Phrase
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P307	IF exposed:
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P321
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P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
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P413
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P422
P402 + P404	Store in a dry place. Store in a closed container.
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P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 615-42-9 ] {[proInfo.proName]}

Quality Control of [ 615-42-9 ]

Related Doc. of [ 615-42-9 ]

Product Details of [ 615-42-9 ]

Calculated chemistry of [ 615-42-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 615-42-9 ]

Application In Synthesis of [ 615-42-9 ]

[ 615-42-9 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 615-42-9 ]

Aryls

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 615-42-9 ]