Name: 4119-41-9|1-Iodo-3-phenylpropane|98% (stabilized with Copper chip)
Brand: Ambeed
SKU: A612779
Price: 13.0 USD
Availability: InStock
Rating: 91 (30 reviews)

1
[ 122-97-4 ]
[ 4119-41-9 ]

Yield	Reaction Conditions	Operation in experiment
92%		General procedure: <strong>[122-97-4]3-Phenyl-1-propanol</strong> 7 (2.0mmol) or trans-4-phenylcyclohexanol (2.0mmol) was dissolved in anhydrous acetonitrile (20mL). Carbonyldiimidazole (2.2mmol) was then added. The reaction was stirred for one hour at room temperature, at which alcohol 7 was fully consumed. Then, potassium halide salts (10mmol), freshly azeotroped p-toluenesulfonic acid (8.0mmol), and dibenzo-18-crown-6 (0.2mmol) were sequentially added. After allowing the mixture to stir at gentle reflux for 24h, the reaction was quenched with DI H20 and extracted with ethyl acetate. The organic layers were then combined, dried with sodium sulfate, and concentrated under vacuum. The crude material was analyzed by GC-MS and then purified by silica-gel column chromatography.
81%	With iodine; In acetonitrile; at 120℃; for 0.05h;Microwave irradiation;	General procedure: To a suspension of polymer-bound triphenylphosphine (1.2 mmol) in anhydrous acetonitrile (10 mL) were added iodine (1 mmol) and 1,6-hexanediol diol (1mmol). The reaction mixture was irradiated in microwave reactor at 120 C for 3 min. The reaction mixture was filtered over a filter paper and washed with chloroform.The filtrate was extracted with aqueous sodium thiosulfate solution and dried with anhydrous sodium sulfate.The reafter, solvent was removed under reduced pressure to obtain 6-iodohexan-1-ol (30) in 93%
72 - 85%	With 1H-imidazole; iodine; triphenylphosphine; In diethyl ether; acetonitrile; at 20℃; for 4 - 5h;	A round bottom flask was charged with phenylalkyl alcohol 1 (1 equiv.), acetonitrile/diethyl ether mixture (1 :2), triphenyl phosphine (1.3 equiv.), imidazole (1.3 equiv.), and iodine (1.3 equiv.). The solution was blanketed with argon and capped and the reaction stirred for 4-5 <n="31"/>hours at room temperature. The resulting mixture diluted with diethyl ether, washed with water, aqueous sodium thiosulfate, and brine, dried (MgSO4) and evaporated. Purification by flash column chromatography on silica gel (10% diethyl ether-hexane) gave phenylalkyl iodide 2 in 72-85% yield.

	With 1H-imidazole; iodine; triphenylphosphine; In diethyl ether; acetonitrile; at 20℃; for 4 - 5h;	A round bottom flask was charged with phenylalkyl alcohol (1) (1 equiv.), acetom'trile/diethyl ether mixture (1 :2), triphenyl phosphine (1.3 equiv.), imidazole (1.3 equiv.), and iodine (1.3 equiv.). The solution was blanketed with argon and capped, and the reaction stirred for 4-5 hours at RT. The resulting mixture was diluted with diethyl ether, washed with water, aqueous sodium thiosulfate, and brine, dried (MgSO4), and evaporated. Purification by flash column chromatography on silica gel (10% diethyl ether-hexane) gave phenylalkyl iodide 2 in 72-85% yield.
	With 1H-imidazole; iodine; triphenylphosphine; In diethyl ether; acetonitrile; at 0 - 20℃; for 12h;	General procedure: Iodination: To a solution of triphenylphosphine (1.97 g, 7.5 mmol, 3.0 equiv) and imidazole (0.58 g, 8.5 mmol, 3.4 equiv) in Et2O:CH3CN = 3:1 (25 mL) was added I2 (1.90 g, 7.5 mmol, 3.0 equiv) slowly at 0 oC. After stirred for 30 minutes, add N-tosylated alcohol (2.5 mmol) to the solution dropwise. The mixture was stirred for 12 hours at room temperature. Check the progress of the reaction by TLC, the reaction mixture was quenched with saturated NH4Cl aqueous solution and extracted by CH2Cl2. The organic layer was dried over MgSO4 and concentrated under the vacuum. Flash column chromatography provided the iodinated products
	With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; at 20℃; for 5h;	General procedure: General Procedure C A flame-dried flask with Teflon stir bar was charged with triphenylphosphine (1.2 equiv.) and I2(1.2 equiv.) in CH2Cl2, the mixture was stirred for 10 min at room temperature. Imidazole (1.2equiv.) was added to the resulting mixture. After 10 min of stirring, the corresponding alcohol(1.0 equiv.) was added and the reaction was stirred for additional 5 h at room temperature andwas checked by TLC until completion. The reaction mixture was quenched with Sat. Na2SO3.The mixture was transferred to a separatory funnel using CH2Cl2 and brine to aid the transferand separation. The aqueous and organic layers were separated and the aqueous layer wasextracted by CH2Cl2 (3x). The combined organic layers were washed with brine and dried overNa2SO4, filtered, and concentrated in vacuum. The crude reaction mixture was purified by flashchromatograph on silica gel and evaporated to give the alkyl iodide compound.

Reference： [1]Chemical and pharmaceutical bulletin,1983,vol. 31,p. 4189 - 4192
[2]Journal of the American Chemical Society,2010,vol. 132,p. 1740 - 1741
[3]Canadian Journal of Chemistry,2006,vol. 84,p. 1006 - 1012
[4]Tetrahedron Letters,2004,vol. 45,p. 7451 - 7454
[5]Tetrahedron Letters,2015,vol. 56,p. 1392 - 1396
[6]Tetrahedron Letters,2006,vol. 47,p. 1771 - 1775
[7]Journal of the American Chemical Society,2001,vol. 123,p. 12160 - 12167
[8]Journal of the American Chemical Society,2017,vol. 139,p. 8110 - 8113
[9]Synthetic Communications,2006,vol. 36,p. 91 - 95
[10]Organic Preparations and Procedures International,2009,vol. 41,p. 87 - 91
[11]Synthesis,1983,p. 460 - 461
[12]Acta Chimica Slovenica,2015,vol. 62,p. 775 - 783
[13]European Journal of Organic Chemistry,2015,vol. 2015,p. 81 - 85
[14]Patent: WO2008/13963,2008,A2 .Location in patent: Page/Page column 29-30
[15]Angewandte Chemie - International Edition,2020,vol. 59,p. 6750 - 6755
    Angew. Chem.,2020,vol. 132,p. 6816 - 6821,6
[16]Tetrahedron Letters,2003,vol. 44,p. 8143 - 8147
[17]Zeitschrift fur Physikalische Chemie (Leipzig),1932,vol. <A> 161,p. 46,56
[18]Zhurnal Russkago Fiziko-Khimicheskago Obshchestva,1905,vol. 37,p. 663
    Chemisches Zentralblatt,1905,vol. 76,p. 1017
[19]Chemistry Letters,1976,p. 619 - 622
[20]Chemistry Letters,1976,p. 267 - 270
[21]Chemistry Letters,1976,p. 373 - 374
[22]Tetrahedron Letters,2003,vol. 44,p. 5799 - 5801
[23]Tetrahedron Letters,2003,vol. 44,p. 5799 - 5801
[24]Chemische Berichte,1910,vol. 43,p. 2842
[25]Patent: WO2009/52319,2009,A1 .Location in patent: Page/Page column 65
[26]Synlett,2012,vol. 23,p. 2692 - 2698,7
[27]Angewandte Chemie - International Edition,2013,vol. 52,p. 933 - 937
    Angew. Chem.,2012,vol. 125,p. 967 - 971,5
[28]Organic Letters,2017,vol. 19,p. 5553 - 5556
[29]Patent: US2018/30074,2018,A1
[30]Bulletin of the Korean Chemical Society,2018,vol. 39,p. 695 - 698
[31]Angewandte Chemie - International Edition,2018,vol. 57,p. 14085 - 14089
    Angew. Chem.,2018,vol. 130,p. 14281 - 14285,5
[32]Chemistry - A European Journal,2019,vol. 25,p. 6290 - 6294
[33]Journal of the American Chemical Society,2019,vol. 141,p. 12464 - 12469
[34]Chem,2020,vol. 6,p. 675 - 688
[35]Organic Letters,2020,vol. 22,p. 3245 - 3250

2
[ 104-52-9 ]
[ 4119-41-9 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 8405 - 8410
[2]Organic Letters,2019
[3]Chemische Berichte,1910,vol. 43,p. 2842
[4]Gazzetta Chimica Italiana,1960,vol. 90,p. 660 - 670

3
[ 2346-00-1 ]
[ 4119-41-9 ]
[ 55089-11-7 ]

Reference： [1]Journal of Organic Chemistry,1975,vol. 40,p. 2021 - 2025

4
[ 4832-52-4 ]
[ 4119-41-9 ]
[ 111171-84-7 ]

Reference： [1]Tetrahedron,1987,vol. 43,p. 1847 - 1856

5
[ 4119-41-9 ]
[ 89414-27-7 ]
[ 89414-34-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 12h;

Reference： [1]Trost, Barry M.; Quayle, Peter [Journal of the American Chemical Society, 1984, vol. 106, # 8, p. 2469 - 2471]

6
[ 4119-41-9 ]
[ 31912-02-4 ]
ethyl 2-(2-nitrophenyl)-5-phenylpentanoate [ No CAS ]

Reference： [1]Synthetic Communications,1995,vol. 25,p. 1 - 8

7
[ 637-59-2 ]
[ 4119-41-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium iodide In acetone for 6h; Reflux;
97%	With sodium iodide In acetone Reflux;
95%	With potassium iodide In acetone for 2h; Reflux;

95%	With sodium iodide In acetone at 20℃; for 16h; Inert atmosphere;
83%	With sodium iodide In acetone Reflux;
63%	With sodium iodide In acetone at 20℃; for 20h;
	With sodium iodide In butanone
	With sodium iodide In acetone at 20℃; Inert atmosphere; Reflux;
	With sodium iodide In acetone for 6h; Reflux;
	Multi-step reaction with 2 steps 1: Caswell No_. 744A / N,N-dimethyl-formamide / 18 h / 80 °C / Inert atmosphere 2: tert-Butyl iodide / dichloromethane / 18 h / 20 °C / Inert atmosphere

Reference： [1]Wang, Xiaoling; Ji, Xiaoming; Shao, Changdong; Zhang, Yu; Zhang, Yanghui [Organic and Biomolecular Chemistry, 2017, vol. 15, # 26, p. 5616 - 5624]
[2]Bouillon, Jean-Philippe; Couve-Bonnaire, Samuel; Pannecoucke, Xavier; Xiao, Pan [Advanced synthesis and catalysis, 2020, vol. 362, # 4, p. 949 - 954]
[3]Bekere, Laura; Lokshin, Vladimir; Sigalov, Mark; Gvishi, Raz; Zhao, Peng; Hagan, David J.; Van Stryland, Eric W.; Khodorkovsky, Vladimir [New Journal of Chemistry, 2016, vol. 40, # 2, p. 1143 - 1148]
[4]Koo, Seung Moh; Vendola, Alex J.; Momm, Sarah Noemi; Morken, James P. [Organic Letters, 2020, vol. 22, # 2, p. 666 - 669]
[5]Li, Songyi; Lian, Chang; Mo, Fanyang; Qiu, Di; Yue, Guanglu; Zhang, Jianning [Journal of Organic Chemistry, 2022, vol. 87, # 6, p. 4291 - 4297]
[6]Wempe [Journal of Molecular Structure, 2001, vol. 562, # 1-3, p. 63 - 78]
[7]Ornstein, Paul L.; Bleisch, Thomas J.; Arnold, M. Brian; Wright, Rebecca A.; Johnson, Bryan G.; Schoepp, Darryle D. [Journal of Medicinal Chemistry, 1998, vol. 41, # 3, p. 346 - 357]
[8]Madsen, Andreas S.; Kristensen, Helle M. E.; Lanz, Gyrithe; Olsen, Christian A. [ChemMedChem, 2014, vol. 9, # 3, p. 614 - 626]
[9]Shen, Peng-Xiang; Wang, Xiao-Chen; Wang, Peng; Zhu, Ru-Yi; Yu, Jin-Quan [Journal of the American Chemical Society, 2015, vol. 137, # 36, p. 11574 - 11577]
[10]Maury, Julien; Feray, Laurence; Bertrand, Michele P.; Kapat, Ajoy; Renaud, Philippe [Tetrahedron, 2012, vol. 68, # 47, p. 9606 - 9611,6]

8
[ 4119-41-9 ]
[ 14402-93-8 ]
[ 2189-60-8 ]

Yield	Reaction Conditions	Operation in experiment
64%	With ethyl (E)-crotonate In tetrahydrofuran at -25℃; for 24h;

Reference： [1]Giovannini, Riccardo; Stüdemann, Thomas; Dussin, Gaelle; Knochel, Paul [Angewandte Chemie - International Edition, 1998, vol. 37, # 17, p. 2387 - 2390]

9
[ 4119-41-9 ]
[ 103-65-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 80℃; for 1h;
62%	With naphthalene; lithium In tetrahydrofuran at -78℃; Electrolysis;
100 % Chromat.	With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 60℃; for 2h;

99 % Chromat.	With air; poly(methylhydrosiloxane) In 1,2-dimethoxyethane at 90℃; for 1h;
97 %Spectr.	With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); sodium trimethylsilanolate In tetrahydrofuran-d8 at 45℃; for 16h; Inert atmosphere; Glovebox; Sealed tube;

Reference： [1]Oderinde, Martins S.; Froese, Robert D. J.; Organ, Michael G. [Angewandte Chemie - International Edition, 2013, vol. 52, # 43, p. 11334 - 11338][Angew. Chem., 2013, vol. 125, # 43, p. 11544 - 11548,5]
[2]Wood, Natasha C. L.; Paddon, Christopher A.; Bhatti, Farrah L.; Donohoe, Timothy J.; Compton, Richard G. [Journal of Physical Organic Chemistry, 2007, vol. 20, # 10, p. 732 - 742]
[3]Suga, Seiji; Manabe, Takao; Yoshida, Jun-Ichi [Chemical Communications, 1999, # 13, p. 1237 - 1238]
[4]Miura, Katsukiyo; Tomita, Mitsuru; Yamada, Yusuke; Hosomi, Akira [Journal of Organic Chemistry, 2007, vol. 72, # 3, p. 787 - 792]
[5]Ravn, Anne K.; Johansen, Martin B.; Skrydstrup, Troels [Angewandte Chemie - International Edition, 2022, vol. 61, # 4][Angew. Chem., 2022, vol. 134, # 4]

10
[ 13483-31-3 ]
[ 4119-41-9 ]
[ 14171-89-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Acetone dimethylhydrazone With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: 1-iodo-3-phenylpropan In tetrahydrofuran; hexane at 0 - 25℃; Stage #3: With sulfuric acid In tetrahydrofuran; hexane at 25℃; for 1h; Further stages.;

Reference： [1]Wrobleski; Aube [Journal of Organic Chemistry, 2001, vol. 66, # 3, p. 886 - 889]

11
[ 4119-41-9 ]
[ 5674-01-1 ]
[ 502760-20-5 ]

Yield	Reaction Conditions	Operation in experiment
69%	With CoCl₂(1,4-bis(diphenylphosphanyl)propane) In tetrahydrofuran at -40℃;
69%	With 1,3-bis-(diphenylphosphino)propane; cobalt(II) chloride In tetrahydrofuran at -40℃; for 2h; Inert atmosphere;
68%	With 1,3-bis-(diphenylphosphino)propane In tetrahydrofuran at -40℃;

Reference： [1]Tsuji, Takashi; Yorimitsu, Hideki; Oshima, Koichiro [Angewandte Chemie - International Edition, 2002, vol. 41, # 21, p. 4137 - 4139]
[2]Zhang, Dequan; You, Cai; Li, Xiuxiu; Wen, Jialin; Wen, Jialin; Zhang, Xumu [Organic Letters, 2020, vol. 22, # 11, p. 4523 - 4526]
[3]Ohmiya, Hirohisa; Tsuji, Takashi; Yorimitsu, Hideki; Oshima, Koichiro [Chemistry - A European Journal, 2004, vol. 10, # 22, p. 5640 - 5648]

12
[ 4119-41-9 ]
[ 2622-05-1 ]
[ 1588-44-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With CoCl₂(1,4-bis(diphenylphosphanyl)propane) In tetrahydrofuran at -40℃;
82%	With 1,3-bis-(diphenylphosphino)propane In tetrahydrofuran at -40℃; for 2h;

Reference： [1]Tsuji, Takashi; Yorimitsu, Hideki; Oshima, Koichiro [Angewandte Chemie - International Edition, 2002, vol. 41, # 21, p. 4137 - 4139]
[2]Ohmiya, Hirohisa; Tsuji, Takashi; Yorimitsu, Hideki; Oshima, Koichiro [Chemistry - A European Journal, 2004, vol. 10, # 22, p. 5640 - 5648]

13
[ 4119-41-9 ]
[ 21969-32-4 ]
[ 26447-66-5 ]
3-methyl-6-phenyl-1-hexene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 93% 2: 1%	With 1,3-bis-(diphenylphosphino)propane In tetrahydrofuran at -40℃;
	With CoCl₂(1,4-bis(diphenylphosphanyl)propane) In tetrahydrofuran at -40℃;

Reference： [1]Ohmiya, Hirohisa; Tsuji, Takashi; Yorimitsu, Hideki; Oshima, Koichiro [Chemistry - A European Journal, 2004, vol. 10, # 22, p. 5640 - 5648]
[2]Tsuji, Takashi; Yorimitsu, Hideki; Oshima, Koichiro [Angewandte Chemie - International Edition, 2002, vol. 41, # 21, p. 4137 - 4139]

14
[ 3742-75-4 ]
[ 4119-41-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium iodide In acetone
93%	With sodium iodide In acetone for 1.5h; Heating;
83%	With sodium iodide In acetone at 20℃; for 6h;	S.8 3-Iodopropylbenzene A reaction vessel was charged with 3-(4-methylphenylsulfonyloxy)propylbenzene (200 mg, 0.688 mmol), sodium iodide (310 mg, 2.07 mmol), and acetone (3.4 mL), and reaction was effected at room temperature for 6 hours. After the reaction, water was added to the reaction system, and the product was extracted three times with ethyl acetate into the organic layer. The resulting organic layer was washed with saturated saline and dried with MgSO4. After concentration under reduced pressure, the concentrate was purified by Hi-flash silica column chromatography (developing solvent, ethyl acetate:hexane=0:100→11:89) to yield a product (140 mg (0.569 mmol), 83% yield, orange liquid). 1H-NMR (600 MHz, CDCl3): δ7.29 (t, J=7.8 Hz, 2H), 7.22 (d, J=7.8 Hz, 1H), 7.20 (d, J=7.8 Hz, 2H), 3.18 (t, J=7.2 Hz, 2H), 2.73 (t, J=7.2 Hz, 2H), 2.14 (quint, J=7.2 Hz, 2H); LRMS (EI) calculated for C9H11I (M+): 246.0, found: 246.0.

Reference： [1]Huang, Pei-Qiang; Li, Zhao-Ying [Tetrahedron Asymmetry, 2005, vol. 16, # 20, p. 3367 - 3370]
[2]Suenaga, Toshiro; Schutz, Caroline; Nakata, Tadashi [Tetrahedron Letters, 2003, vol. 44, # 31, p. 5799 - 5801]
[3]Current Patent Assignee: TOHOKU UNIVERSITY - US2018/30074, 2018, A1 Location in patent: Paragraph 0183-0187

15
[ 201230-82-2 ]
[ 4119-41-9 ]
[ 70950-06-0 ]

Yield	Reaction Conditions	Operation in experiment
71%	With RuHClPNP<SUP>iPr</SUP>(CO); caesium carbonate In toluene at 90℃;
80 % Spectr.	With 2,2'-azobis(isobutyronitrile); hypophosphorous acid; sodium hydrogencarbonate In water at 75℃; for 15h;

Reference： [1]Ai, Han-Jun; Wu, Xiao-Feng; Yuan, Yang [Chemical Science, 2022, vol. 13, # 8, p. 2481 - 2486]
[2]Sugiura, Masaharu; Hagio, Hiroyuki; Kobayashi, Shu [Chemistry Letters, 2003, vol. 32, # 10, p. 898 - 899]

16
[ 4119-41-9 ]
[ 308796-10-3 ]
[ 2189-60-8 ]

Yield	Reaction Conditions	Operation in experiment
60 % Chromat.	In tetrahydrofuran at 20℃; for 23h;
98 % Chromat.	With 4,4',4''-tri-tert-butyl-terpyridine In tetrahydrofuran at 23℃; for 23h;
98 % Chromat.	In tetrahydrofuran at 20℃; for 23h;

Reference： [1]Anderson, Thomas J.; Jones, Gavin D.; Vicic, David A. [Journal of the American Chemical Society, 2004, vol. 126, # 26, p. 8100 - 8101]
[2]Jones, Gavin D.; McFarland, Chris; Anderson, Thomas J.; Vicic, David A. [Chemical Communications, 2005, # 33, p. 4211 - 4213]
[3]Jones, Gavin D.; Martin, Jason L.; McFarland, Chris; Allen, Olivia R.; Hall, Ryan E.; Haley, Aireal D.; Brandon, R. Jacob; Konovalova, Tatyana; Desrochers, Patrick J.; Pulay, Peter; Vicic, David A. [Journal of the American Chemical Society, 2006, vol. 128, # 40, p. 13175 - 13183]

17
[ 4119-41-9 ]
[ 1535-65-5 ]
1,1-difluoro-4-phenylbutyl phenyl sulfone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at -50℃; for 1h;

Reference： [1]Prakash, G.K. Surya; Hu, Jinbo; Wang, Ying; Olah, George A. [Angewandte Chemie - International Edition, 2004, vol. 43, # 39, p. 5203 - 5206] Prakash, G. K. Surya; Hu, Jinbo; Wang, Ying; Olah, George A. [Organic Letters, 2004, vol. 6, # 23, p. 4315 - 4317]

18
[ 4119-41-9 ]
[ 1641-69-6 ]
[ 59616-73-8 ]

Yield	Reaction Conditions	Operation in experiment
34%	With dimethyl sulfoxide; triethylamine In tetrahydrofuran at 35℃; for 0.1h; UV-irradiation;	1; 3 Example 1 - Precursors and Resultant ProductsPrecursors that were used to label acids are shown in List. 1. EPO Iodo-cyclohexane1-Iodo-butane//^IodohexadecaneList 1. Iodides used as precursors in the synthesis of labeled acidsThe following experiments illustrate the present invention. Radical carboxylation using submicromolar amounts of [ϖC]carbon monoxide is performed yielding labeled with the acids shown in Table 1 as target compounds. Table 1 Radiochemical yields for λ ^-labelled acids; Example 3 - Preparation of carboxyl-n C] acidsGeneral procedure.; Triethylamine (25 juL) was placed in a capped vial (1 mL, flushed beforehand with nitrogen to remove oxygen) and dissolved in DMSO (500 μL). An alkyl or aryl iodide (0.1 /anol) was added to the solution ca. 7 min before the start of the synthesis. The resulting mixture was pressurized (over 40 MPa) into the micro-autoclave (270 μL), pre-charged with [nC]carbon monoxide (10"8 -10"9 mol) mixed with He. The mixture was irradiated with a UV source for 6 min with stirring at 35°C. The crude reaction mixture was then transferred from the autoclave to a capped vial, held under reduced pressure. After measurement of the radioactivity the vial was purged with nitrogen and the radioactivity was measured again. The crude product was diluted with acetonitrile or methanol (0.6 mL) and injected on the semi- preparative LC. Analytical LC and LC-MS were used to assess the identity and radiochemical purity of the collected fraction.
	In tetrahydrofuran; water at 35℃; for 1h; Irradiation;

Reference： [1]Current Patent Assignee: GENERAL ELECTRIC CO - WO2006/134474, 2006, A2 Location in patent: Page/Page column 25-26; 28
[2]Itsenko, Oleksiy; Langstroem, Bengt [Journal of Organic Chemistry, 2005, vol. 70, # 6, p. 2244 - 2249]

19
[ 4119-41-9 ]
[ 10456-04-9 ]
[1-11C]-4-phenylbutyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With water In acetone at 35℃; for 0.1h; UV-irradiation;	1; 3 Example 1 - Precursors and Resultant ProductsPrecursors that were used to label esters and acids are shown in List. 1.Iodo-cyclohexane(3-Iodo-propyI)-benzene11 -Iodo-undecanoic acidList Ia. Iodides used as precursors in the synthesis of labeled esters and acidsy- OHPropan-2-olCH3OHMethanol List Ib. Alcohols used as precursors in the synthesis of labeled esters EPO The following experiments illustrate the present invention. Radical carbonylation using submicromolar amounts of [nC]carbon monoxide is performed yielding labeled esters and acids shown in Table 1 as target compounds. Table 1, Radiochemical yields of labeled compounds.THF/IPAd (l:l) 47+3 79+/-1 38+3 85 71 5985+2 80+/-3 67+1 a The position of "C label is denoted by an asterisk. " Decay-corrected radiochemical yield determined by LC. ° Number of runs. d IPA is Propan-2-ol; Example 3 - Preparation of carbonyl~ Cl esters and acids EPO General procedure: An alcohol (200 /anol) or water and a photosensitizer (Table 1) were placed in a capped vial (1 mL, flushed beforehand with nitrogen to remove air) and dissolved in THF (500 /JL); in some cases the alcohol was used as a solvent instead of THF. An iodide (100 μmo) was added to the solution ca. 7 min before the start of the synthesis. The resulting mixture was pressurized (over 40 MPa) into the autoclave, pre-charged with [uC]carbon monoxide (10"8 -10"9 mol) and helium gas mixture. The mixture was irradiated with the Xe-Hg lamp for 6 min with stirring at 35°C. The crude reaction mixture was then transferred from the autoclave to a capped vial, held under reduced pressure. After measurement of the radioactivity the vial was purged with nitrogen and the radioactivity was measured again. The crude product was diluted with acetonitrile or methanol (0.6 mL) and injected on the semi- preparative LC. Analytical LC and LC-MS were used to assess the identity and radiochemical purity of the collected fractions.
51%	With potassium hydroxide In tetrahydrofuran; water at 35℃; Autoclave; UV-irradiation; Inert atmosphere;	1.4a; 3 Example 1; Precursors and Resultant Products; Precursors that were used to label acids are shown in List. 1. List 1. Iodides used as precursors in the synthesis of labeled acids The following experiments illustrate the present invention. Radical carboxylation using submicromolar amounts of [11C]carbon monoxide is performed yielding labeled with the acids shown in Table 1 as target compounds.; Example 3; Preparation of [carboxyl-11C] acids; General procedure.; An iodide (100 μmol) was placed in a capped vial (1 mL, flushed beforehand with nitrogen to remove oxygen) and dissolved in THF (400 μL). Water (100 μL) and an optional additive were added to the solution ca. 7 min before the start of the synthesis. The resulting mixture was pressurized (over 40 MPa) into the micro-autoclave (270 μL), pre-charged with [11C]carbon monoxide (10-8-10-9 mol) mixed with He. The mixture was irradiated with a UV source for 5-7 min with stirring at 35° C. The crude reaction mixture was then transferred from the autoclave to a capped vial, held under reduced pressure. After measurement of the radioactivity the vial was purged with nitrogen and the radioactivity was measured again. The crude product was diluted with acetonitrile or methanol (0.6 mL) and injected on the semi-preparative LC. Analytical LC and LC-MS were used to assess the identity and radiochemical purity of the collected fraction.
	In tetrahydrofuran; water at 30℃; Irradiation;

	With water In tetrahydrofuran at 35℃; for 0.1h; Irradiation;
	With dimethyl sulfoxide; triethylamine at 30 - 35℃; for 0.1h; UV-irradiation;
68 %Chromat.	With potassium hydroxide; water In tetrahydrofuran at 35℃; for 0.0833333 - 0.116667h; UV-irradiation;	1.4a; 3 .Example 1; - Precursors and Resultant ProductsPrecursors that were used to label acids are shown in List. 1.2-Iodo-propaneIodo-cyclohexane1-Iodo-butane4-(3-Iodo-proρyl)-ρhenol12-Iodo-2-methyl-propane5-Iodo-ρent-l-eneIodododecane EPO 11-Iodo-undecanoic acid1 -Iodo-adamantaneList 1. Iodides used as precursors in the synthesis of labeled acidsThe following experiments illustrate the present invention. Radical carboxylation using submicromolar amounts of [l C]carbon monoxide is performed yielding labeled with the acids shown in Table 1 as target compounds. Table 1 Radiochemical yields for l ^-labelled acidsAdditiveEntry Labelled compounda Solvents c [on CvJ°. Y f0/ieΛld* Y.i0el,lfd d (mmol)J .0TΗF/H2O (4:1) TBAOH (0.03) 82+2 80+2 70+2OHACN/H2O (3:2) KOH (0.04) 84+/-1 81+1 67+/-4THFZH2O (4:1) TBAOH (0.03) 81+3 74+2 59+/-74a THF/H2O (4:1) KOH (0.04) 79 68 51 4b THF/H2O (4:1) 73+5 62+5 <1 EPO O7 THFVH2O (4:1) TBAOH (0.03) 36 d - v/ςvOH8 THFZH2O (4:1) TBAOH (0.03) 82+2 73+2 55+49a THFZH2O (9:1) TBAOH (0.03) 82 68 52 THFZacetoneZH2O 9b (3:1:1) 91+4 82+4 65+410a THFZH2O (4:1) TBAOH (0.13) 84 76 10b THFZH2O (4:1) 37 34 - ACNZH2O (4:1) KOH (0.1) 81+6 77+5 63+4 ACNZH2O (9:1) TBAOH (0.2) 94 56 33 THFZH2O (9:1) TBAOH (0.15) 90 64 55The position of C label is denoted by an asterisk. Decay-corrected radiochemical yield determined by LC. ° Number of runs. d Unseparated peaks; Example 3 - Preparation Qf FCaJrOoXKZ-11Cl acidsGeneral procedure. An iodide (100 /rniol) was placed in a capped vial (1 mL, flushed beforehand with nitrogen to remove oxygen) and dissolved in THF (400 //L). Water (100 //L) and an optional additive were added to the solution ca. 7 min before the start of the synthesis. The resulting mixture was pressurized (over 40 MPa) into the micro-autoclave (270 //L), pre-charged with [ϖC]carbon monoxide (10"8 -10'9 mol) mixed with He. The mixture was irradiated with a UV source for 5-7 min with stirring at 35°C. The crude reaction mixture was then transferred from the autoclave to a capped vial, held under reduced pressure. After measurement of the radioactivity the vial was purged with nitrogen and the radioactivity was measured again. The crude product was diluted with acetonitrile or methanol (0.6 mL) and injected on the EPO semi-preparative LC. Analytical LC and LC-MS were used to assess the identity and radiochemical purity of the collected fraction.(l-13C)4-Phenylbutyric acid was synthesised from (3-iodopropyl)benzene as described in the general procedure. (13C)Carbon monoxide (approximately 0.05 mmol) was added to [nC]carbon monoxide and the reaction was run for 1 h. 1H NMR (400MHz, CDCl3): δ 10.0 (br s, IH), 7.35-7.18 (m, 5H), 2.70 (m, 2H), 2.41 (m, 2JH13C=7.3HZ, 2H), 2.00 (m, 3JH13C=4.4HZ, 2H). 13C NMR (100MHZ, CDCl3): δ 180.5, 141.2, 128.5, 128.4, 126.0, 34.9 (d, 2J13c13c =3.8Hz), 33.0 (d, 1J13C13C=SSJHz), 26.2.
62 %Chromat.	With water In tetrahydrofuran at 35℃; for 0.0833333 - 0.116667h; UV-irradiation;	1.4b; 3 .Example 1; - Precursors and Resultant ProductsPrecursors that were used to label acids are shown in List. 1.2-Iodo-propaneIodo-cyclohexane1-Iodo-butane4-(3-Iodo-proρyl)-ρhenol12-Iodo-2-methyl-propane5-Iodo-ρent-l-eneIodododecane EPO 11-Iodo-undecanoic acid1 -Iodo-adamantaneList 1. Iodides used as precursors in the synthesis of labeled acidsThe following experiments illustrate the present invention. Radical carboxylation using submicromolar amounts of [l C]carbon monoxide is performed yielding labeled with the acids shown in Table 1 as target compounds. Table 1 Radiochemical yields for l ^-labelled acidsAdditiveEntry Labelled compounda Solvents c [on CvJ°. Y f0/ieΛld* Y.i0el,lfd d (mmol)J .0TΗF/H2O (4:1) TBAOH (0.03) 82+2 80+2 70+2OHACN/H2O (3:2) KOH (0.04) 84+/-1 81+1 67+/-4THFZH2O (4:1) TBAOH (0.03) 81+3 74+2 59+/-74a THF/H2O (4:1) KOH (0.04) 79 68 51 4b THF/H2O (4:1) 73+5 62+5 <1 EPO O7 THFVH2O (4:1) TBAOH (0.03) 36 d - v/ςvOH8 THFZH2O (4:1) TBAOH (0.03) 82+2 73+2 55+49a THFZH2O (9:1) TBAOH (0.03) 82 68 52 THFZacetoneZH2O 9b (3:1:1) 91+4 82+4 65+410a THFZH2O (4:1) TBAOH (0.13) 84 76 10b THFZH2O (4:1) 37 34 - ACNZH2O (4:1) KOH (0.1) 81+6 77+5 63+4 ACNZH2O (9:1) TBAOH (0.2) 94 56 33 THFZH2O (9:1) TBAOH (0.15) 90 64 55The position of C label is denoted by an asterisk. Decay-corrected radiochemical yield determined by LC. ° Number of runs. d Unseparated peaks; Example 3 - Preparation Qf FCaJrOoXKZ-11Cl acidsGeneral procedure. An iodide (100 /rniol) was placed in a capped vial (1 mL, flushed beforehand with nitrogen to remove oxygen) and dissolved in THF (400 //L). Water (100 //L) and an optional additive were added to the solution ca. 7 min before the start of the synthesis. The resulting mixture was pressurized (over 40 MPa) into the micro-autoclave (270 //L), pre-charged with [ϖC]carbon monoxide (10"8 -10'9 mol) mixed with He. The mixture was irradiated with a UV source for 5-7 min with stirring at 35°C. The crude reaction mixture was then transferred from the autoclave to a capped vial, held under reduced pressure. After measurement of the radioactivity the vial was purged with nitrogen and the radioactivity was measured again. The crude product was diluted with acetonitrile or methanol (0.6 mL) and injected on the EPO semi-preparative LC. Analytical LC and LC-MS were used to assess the identity and radiochemical purity of the collected fraction.(l-13C)4-Phenylbutyric acid was synthesised from (3-iodopropyl)benzene as described in the general procedure. (13C)Carbon monoxide (approximately 0.05 mmol) was added to [nC]carbon monoxide and the reaction was run for 1 h. 1H NMR (400MHz, CDCl3): δ 10.0 (br s, IH), 7.35-7.18 (m, 5H), 2.70 (m, 2H), 2.41 (m, 2JH13C=7.3HZ, 2H), 2.00 (m, 3JH13C=4.4HZ, 2H). 13C NMR (100MHZ, CDCl3): δ 180.5, 141.2, 128.5, 128.4, 126.0, 34.9 (d, 2J13c13c =3.8Hz), 33.0 (d, 1J13C13C=SSJHz), 26.2.

Reference： [1]Current Patent Assignee: GENERAL ELECTRIC CO - WO2006/131803, 2006, A2 Location in patent: Page/Page column 25-28
[2]Current Patent Assignee: GENERAL ELECTRIC CO - US7667011, 2010, B2 Location in patent: Page/Page column 13-17
[3]Itsenko, Oleksiy; Langstroem, Bengt [Journal of Organic Chemistry, 2005, vol. 70, # 6, p. 2244 - 2249]
[4]Itsenko, Oleksiy; Langstroem, Bengt [Organic Letters, 2005, vol. 7, # 21, p. 4661 - 4664]
[5]Itsenko, Oleksiy; Kihlberg, Tor; Långström, Bengt [Synlett, 2005, # 20, p. 3154 - 3156]
[6]Current Patent Assignee: GENERAL ELECTRIC CO - WO2006/134424, 2006, A2 Location in patent: Page/Page column 23-24; 26-27
[7]Current Patent Assignee: GENERAL ELECTRIC CO - WO2006/134424, 2006, A2 Location in patent: Page/Page column 23-24; 26-27

20
[ 4119-41-9 ]
[ 327060-00-4 ]
N-[3,5-bis-(3-phenyl-propyl)-phenyl]-N-methyltoluenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With isopropylboronic acid; caesium carbonate; triphenylphosphine In acetonitrile for 20h; Heating;

Reference： [1]Wilhelm, Thorsten; Lautens, Mark [Organic Letters, 2005, vol. 7, # 18, p. 4053 - 4056]

21
[ 201230-82-2 ]
[ 4119-41-9 ]
[ 109-89-7 ]
[ 56229-85-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	In benzene for 16h; Photolysis;

Reference： [1]Fukuyama, Takahide; Nishitani, Satoshi; Inouye, Takaya; Morimoto, Keisuke; Ryu, Ilhyong [Organic Letters, 2006, vol. 8, # 7, p. 1383 - 1386]

22
[ 201230-82-2 ]
[ 4119-41-9 ]
[ 109-89-7 ]
N,N-diethyl-2-oxo-5-phenylpentanamide [ No CAS ]
[ 56229-85-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 48% 2: 21%	With P(p-CH₃OC₆H₄)3 In benzene for 16h; Photolysis;

Reference： [1]Fukuyama, Takahide; Nishitani, Satoshi; Inouye, Takaya; Morimoto, Keisuke; Ryu, Ilhyong [Organic Letters, 2006, vol. 8, # 7, p. 1383 - 1386]

23
[ 10486-61-0 ]
[ 4119-41-9 ]
[ 140-88-5 ]
2,4-bis(3-phenylpropyl)-3-[2-(ethoxycarbonyl)vinyl]thiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With palladium diacetate; trifuran-2-yl-phosphane; caesium carbonate In acetonitrile at 80℃; for 24h;

Reference： [1]Mitsudo, Koichi; Thansandote, Praew; Wilhelm, Thorsten; Mariampillai, Brian; Lautens, Mark [Organic Letters, 2006, vol. 8, # 18, p. 3939 - 3942]

24
[ 4119-41-9 ]
[ 1087-49-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate In ethanol; water at 80℃; for 8h; Schlenk technique; Sealed tube;
76%	With manganese; (2-(dimethylamino)-N-(quinolin-8-yl)acetamido)nickel(II) chloride In N,N-dimethyl-formamide at 20℃;
70%	With Hexamethylbenzene; 4,4',4''-tri-tert-butyl-terpyridine In benzene for 1h;

With manganese; para-fluorostyrene; (2-(dimethylamino)-N-(quinolin-8-yl)acetamido)nickel(II) chloride In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Glovebox; Sealed tube;

Reference： [1]Wang, Zheng-Jun; Wang, Xia; Lv, Jing-Jing; Feng, Jiu-Ju; Xu, Xinhua; Wang, Ai-Jun; Liang, Zhiwu [New Journal of Chemistry, 2017, vol. 41, # 10, p. 3894 - 3899]
[2]Donslund, Aske S.; Pedersen, Simon S.; Gaardbo, Cecilie; Neumann, Karoline T.; Kingston, Lee; Elmore, Charles S.; Skrydstrup, Troels [Angewandte Chemie - International Edition, 2020, vol. 59, # 21, p. 8099 - 8103][Angew. Chem., 2020, vol. 132, p. 8176 - 8180,5]
[3]Jones, Gavin D.; McFarland, Chris; Anderson, Thomas J.; Vicic, David A. [Chemical Communications, 2005, # 33, p. 4211 - 4213]
[4]Ravn, Anne K.; Johansen, Martin B.; Skrydstrup, Troels [Angewandte Chemie - International Edition, 2022, vol. 61, # 4][Angew. Chem., 2022, vol. 134, # 4]

25
[ 4119-41-9 ]
[ 603-35-0 ]
(3-phenylpropyl)triphenylphosphonium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In acetonitrile for 16h; Heating;
86%	In toluene at 100℃; for 7.5h;
	In 1,4-dioxane at 100℃; for 24h;

Reference： [1]Charette; Molinaro; Brochu [Journal of the American Chemical Society, 2001, vol. 123, # 49, p. 12160 - 12167]
[2]Otani, Takashi; Ueki, Kanako; Cho, Kinryo; Kanai, Kan; Tateno, Kotaro; Saito, Takao [Chemical Communications, 2015, vol. 51, # 37, p. 7895 - 7898]
[3]Location in patent: body text Yao, Fenmei; Li, Chen; Vadivel, Subramanian K.; Bowman, Anna L.; Makriyannis, Alexandros [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 22, p. 5912 - 5915]
[4]Romanov-Michailidis, Fedor; Sedillo, Kassandra F.; Neely, Jamie M.; Rovis, Tomislav [Journal of the American Chemical Society, 2015, vol. 137, # 28, p. 8892 - 8895]

26
[ 4119-41-9 ]
[ 63014-04-0 ]

Yield	Reaction Conditions	Operation in experiment
19%	Stage #1: 1-iodo-3-phenylpropan With tert.-butyl lithium In diethyl ether; hexane; pentane at -78 - 78℃; for 0.2h; Stage #2: With sulfuryl dichloride In diethyl ether; hexane; pentane at -78 - 20℃; for 4.33333h;	1 A solution of phenylalkyl iodide 2 (1 equiv.) in a mixture of dry n-pentane/diethyl ether (3:2) was cooled to -780C under argon, and M3uL (2.2 equiv., using a 1.7 M solution of t-BulΛ in hexane) was added dropwise over a 2-min period. The mixture was stirred for 10 min at - 780C and then was transferred by cannula to a cooled (-780C) and dry solution of SO2Cl2 in «-pentane over a 20-min period. Following the addition, the reaction mixture was stirred for 1 hour at - 78°C and then allowed to warm to room temperature over a 3 hours period. The reaction mixture was quenched with dropwise addition of water, then diluted with diethyl ether and the organic phase was separated. The aqueous phase was extracted with diethyl ether, the combined organic layer was dried (MgSO^ and the solvent was evaporated. Purification by flash column chromatography on silica gel gave phenylalkyl sulfonyl chloride 3 in 19-23% yield.
19%	Stage #1: 1-iodo-3-phenylpropan With tert.-butyl lithium In diethyl ether; hexane; pentane at -78℃; for 0.166667h; Inert atmosphere; Stage #2: With sulfuryl dichloride In diethyl ether; hexane; pentane at -78℃; for 1h; Inert atmosphere;
	Stage #1: 1-iodo-3-phenylpropan With tert.-butyl lithium In diethyl ether; hexane; pentane at -78℃; for 0.2h; Stage #2: With sulfuryl dichloride In diethyl ether; hexane; pentane at -78 - 20℃; for 4.33333h;	B A solution of phenylalkyl iodide (2) (1 equiv.) in a mixture of dry n- pentane/diethyl ether (3:2) was cooled to -78°C under argon, and /-BuLi (2.2 equiv., using a 1.7 M solution of Z-BuLi in hexane) was added dropwise over a 2-min period. The mixture was stirred for 10 min at -78°C and then was transferred by cannula to a cooled (-78°C) and dry solution Of SO2Cl2 in «-pentane over a 20-min period. Following the addition, the reaction mixture was stirred for 1 hour at -78°C and then allowed to warm to RT over a 3 hour period. The reaction mixture was quenched with dropwise addition of water, then diluted with diethyl ether and the organic phase was separated. The aqueous phase was extracted with diethyl ether, the combined organic layer was dried (MgSθ4), and the solvent was evaporated. Purification by flash column chromatography on silica gel gave phenylalkylsulfonyl chloride 3 in 19-23% yield.

Reference： [1]Current Patent Assignee: UNIVERSITY OF CONNECTICUT - WO2008/13963, 2008, A2 Location in patent: Page/Page column 30
[2]Alapafuja, Shakiru O.; Nikas, Spyros P.; Bharathan, Indu T.; Shukla, Vidyanand G.; Nasr, Mahmoud L.; Bowman, Anna L.; Zvonok, Nikolai; Li, Jing; Shi, Xiaomeng; Engen, John R.; Makriyannis, Alexandros [Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 10074 - 10089]
[3]Current Patent Assignee: NORTHEASTERN UNIVERSITY IN BOSTON, MASSACHUSETTS - WO2009/52319, 2009, A1 Location in patent: Page/Page column 65-66

27
[ 4119-41-9 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
68 % Chromat.	With lithium bromide In tetrahydrofuran at 20℃; for 24h;

Reference： [1]Organ, Michael G.; Avola, Stephanie; Dubovyk, Igor; Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Valente, Gory [Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4749 - 4755]

28
6-(1,4-Diazepan-1-yl)-1-(4,4,4-trifluorobutyl)-benzo[cd]indol-2(1H)-one [ No CAS ]
[ 4119-41-9 ]
6-[4-(3-Phenylpropyl)-1,4-diazepan-1-yl]-1-(4,4,4-trifluorobutyl)-benzo[cd]indol-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With potassium carbonate In acetonitrile at 20℃; for 18h;	1.4 [00109] Step 4: 6-[4-(3-Phenylpropyl)-1,4diazepan-1-yl]-1-(4,4,4-trifluorobutyl)benzo [cd]indol-2(1H)-one [00110] The crude product from step 3 was dissolved in 30 ml acetonitrile and distributed into 30 vials (2 ml size) preloaded with potassium carbonate (300 mg, 2.3 mmol). Next, 1-bromo-3-phenylporpane (135 μl, 0.135 mmol) was then added and the mixture was shaked on a robital shaker for 18 hours at room temperature. The reaction was then worked up by pipetting out most of the solution and running through a prep HPLC using the Gilson system. The product (62 mg, 54%) was obtained by stripping off the solvent on a speed-vac.

Reference： [1]Current Patent Assignee: PFIZER INC - US6667303, 2003, B1 Location in patent: Page column 19

29
[ 4119-41-9 ]
[ 10456-04-9 ]
C₁₅⁽¹¹⁾CH₁₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	Stage #1: 1-iodo-3-phenylpropan; phenol With n-butyllithium In tetrahydrofuran for 0.116667h; Stage #2: 11C-carbon monooxide In tetrahydrofuran at 35℃; for 0.1h; UV-irradiation;	3 General procedure: An alcohol (200 μoaol) and appropriate base (Table 1) was placed in a capped vial (1 mL, flushed beforehand with nitrogen to remove air) and dissolved in THF (500 //L); in some cases the alcohol was used as a solvent instead of THF. An iodide (100 //mol) was added to the solution ca. 7 min before the start of the synthesis. The resulting mixture was pressurized (over 40 MPa) into the autoclave, pre-charged with [ϖC]carbon monoxide (10~8 -10"9 mol) and helium gas mixture. The mixture was irradiated with the Xe-Hg lamp for 6 min with stirring at 350C. The crude reaction mixture was then transferred from the autoclave to a capped vial, held under reduced pressure. After measurement of the radioactivity the vial was purged with nitrogen and the radioactivity was measured again. The crude product was diluted with acetonitrile or methanol (0.6 mL) and injected on the semi-preparative LC. Analytical LC and LC-MS were used to assess the identity and radiochemical purity of the collected fractions.
38%	Stage #1: 1-iodo-3-phenylpropan; phenol With potassium hydroxide In tetrahydrofuran; water for 0.116667h; Stage #2: 11C-carbon monooxide In tetrahydrofuran; water at 35℃; for 0.1h; UV-irradiation;	3 General procedure: An alcohol (200 μoaol) and appropriate base (Table 1) was placed in a capped vial (1 mL, flushed beforehand with nitrogen to remove air) and dissolved in THF (500 //L); in some cases the alcohol was used as a solvent instead of THF. An iodide (100 //mol) was added to the solution ca. 7 min before the start of the synthesis. The resulting mixture was pressurized (over 40 MPa) into the autoclave, pre-charged with [ϖC]carbon monoxide (10~8 -10"9 mol) and helium gas mixture. The mixture was irradiated with the Xe-Hg lamp for 6 min with stirring at 350C. The crude reaction mixture was then transferred from the autoclave to a capped vial, held under reduced pressure. After measurement of the radioactivity the vial was purged with nitrogen and the radioactivity was measured again. The crude product was diluted with acetonitrile or methanol (0.6 mL) and injected on the semi-preparative LC. Analytical LC and LC-MS were used to assess the identity and radiochemical purity of the collected fractions.

Reference： [1]Current Patent Assignee: GENERAL ELECTRIC CO - WO2006/64349, 2006, A1 Location in patent: Page/Page column 25; 27
[2]Current Patent Assignee: GENERAL ELECTRIC CO - WO2006/64349, 2006, A1 Location in patent: Page/Page column 25; 27

30
[ 4119-41-9 ]
[ 134069-59-3 ]
[ 134070-01-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	In hexane; 4-methyl-2-pentanone	13 Preparation of 1-oxa-2-oxo-3-methyl-4-methylene-8,8-bis(3-phenylpropyl)-3,8-diazaspiro[4,5]decan-8-ium iodide EXAMPLE 13 Preparation of 1-oxa-2-oxo-3-methyl-4-methylene-8,8-bis(3-phenylpropyl)-3,8-diazaspiro[4,5]decan-8-ium iodide 6.0 g of 1-oxa-2-oxo-3-methyl-4-methylene-8-(3-phenylpropyl)-3,8-diazaspiro[4,5]decane are refluxed with 5.4 g of 3-phenylpropyl iodide in 60 ml of methyl isobutyl ketone under nitrogen for 4 hours, then the solvent is distilled off under reduced pressure. After adding hexane to the residue the solid precipitate is filtered and recrystallized from ethanol to give the title compound in 86% yield, m.p.: 219°-220° C.
86%	In hexane; 4-methyl-2-pentanone	13 1-oxa-2-oxo-3-methyl-4-methylene-8,8-bis(3-phenylpropyl)-3,8-diazaspiro[ 4,5]decan-8-ium iodide Example 13 1-oxa-2-oxo-3-methyl-4-methylene-8,8-bis(3-phenylpropyl)-3,8-diazaspiro[ 4,5]decan-8-ium iodide 6.0 g of 1-oxa-2-oxo-3-methyl-4-methylene-8-(3-phenylpropyl)-3,8-diazaspiro[ 4,5]decane are refluxed with 5.4 g of 3-phenylpropyl iodide in 60 ml of methyl isobutyl ketone under nitrogen for 4 hours, then the solvent is distilled off under reduced pressure. After adding hexane to the residue the solid precipitate is filtered and recrystallized from ethanol to give the title compound in 86% yield, m.p.: 219-220 oC.

Reference： [1]Current Patent Assignee: SANOFI; angolul : Chemical Works of Gedeon Richter Plc. Gedeon Richter Plc. - US5118687, 1992, A
[2]Current Patent Assignee: SANOFI; angolul : Chemical Works of Gedeon Richter Plc. Gedeon Richter Plc. - EP414421, 1991, A2

31
[ 4119-41-9 ]
(2-(1,3-dioxolan-2-yl)ethyl)zinc(II) bromide [ No CAS ]
2-(5-phenylpentyl)-1,3-dioxolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With (S)-(s-Bu)-Pybox In tetrahydrofuran at 23℃; for 11h;

Reference： [1]Phapale, Vilas B.; Bunuel, Elena; Garcia-Iglesias, Miguel; Cardenas, Diego J. [Angewandte Chemie - International Edition, 2007, vol. 46, # 46, p. 8790 - 8795]

32
[ 4119-41-9 ]
1-ethylpropylzinc bromide [ No CAS ]
[ 1005002-32-3 ]

Yield	Reaction Conditions	Operation in experiment
	With (S)-(s-Bu)-Pybox In tetrahydrofuran at 23℃; for 18h;

Reference： [1]Phapale, Vilas B.; Bunuel, Elena; Garcia-Iglesias, Miguel; Cardenas, Diego J. [Angewandte Chemie - International Edition, 2007, vol. 46, # 46, p. 8790 - 8795]

33
[ 4119-41-9 ]
[ 524689-75-6 ]
[ 1010447-25-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: S-pent-4-yn-1-yl ethanethioate With potassium hydroxide In methanol at 0℃; for 0.25h; Inert atmosphere; Stage #2: 1-iodo-3-phenylpropan In methanol at 50℃; for 2h;

Reference： [1]Bencivenni, Giorgio; Lanza, Tommaso; Leardini, Rino; Minozzi, Matteo; Nanni, Daniele; Spagnolo, Piero; Zanardi, Giuseppe [Organic Letters, 2008, vol. 10, # 6, p. 1127 - 1130]

34
[ 4119-41-9 ]
[ 159213-03-3 ]
[ 1094537-98-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide With lithium chloride; lithium diisopropyl amide In tetrahydrofuran at -78 - 23℃; for 1h; Inert atmosphere; Stage #2: 1-iodo-3-phenylpropan In tetrahydrofuran at 0℃; for 0.75h; Inert atmosphere;

Reference： [1]Nicewicz, David A.; Satterfield, Andrew D.; Schmitt, Daniel C.; Johnson, Jeffrey S. [Journal of the American Chemical Society, 2008, vol. 130, # 51, p. 17281 - 17283]

35
[ 910650-82-7 ]
[ 4119-41-9 ]
[ 1120341-22-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Prakash, G. K. Surya; Chacko, Sujith; Vaghoo, Habiba; Shao, Nan; Gurung, Laxman; Mathew, Thomas; Olah, George A. [Organic Letters, 2009, vol. 11, # 5, p. 1127 - 1130]

36
[ 40365-61-5 ]
[ 4119-41-9 ]
[ 1123202-81-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: 2-(but-3-yn-1-yloxy)tetrahydropyran With n-butyllithium In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 1-iodo-3-phenylpropan In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hexane at 65℃; for 20h; Inert atmosphere;
	Stage #1: 2-(but-3-yn-1-yloxy)tetrahydropyran With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Inert atmosphere; Stage #2: 1-iodo-3-phenylpropan In tetrahydrofuran; hexane at 23℃; Inert atmosphere;

Reference： [1]Thornton, Aaron R.; Martin, Veronique I.; Blakey, Simon B. [Journal of the American Chemical Society, 2009, vol. 131, p. 2434 - 2435]
[2]Rooke, Douglas A.; Ferreira, Eric M. [Angewandte Chemie - International Edition, 2012, vol. 51, # 13, p. 3225 - 3230]

37
[ 616-47-7 ]
[ 4119-41-9 ]
[ 1141497-98-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: 1-methyl-1H-imidazole With n-butyllithium In tetrahydrofuran; hexane at -50 - -43℃; Stage #2: 1-iodo-3-phenylpropan In tetrahydrofuran; hexane at -43 - 20℃; Inert atmosphere;

Reference： [1]Murphy, John A.; Schoenebeck, Franziska; Findlay, Neil J.; Thomson, Douglas W.; Zhou, Sheng-ze; Garnier, Jean [Journal of the American Chemical Society, 2009, vol. 131, p. 6475 - 6479]

38
[ 122-97-4 ]
[ 1229444-44-3 ]
[ 4119-41-9 ]
[ 1229444-42-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With 1H-imidazole; iodine; potassium iodide In 1,2-dichloro-ethane at 40℃; for 2h;

Reference： [1]Location in patent: scheme or table Imura, Yumi; Shimojuh, Naoya; Kawano, Yuhta; Togo, Hideo [Tetrahedron, 2010, vol. 66, # 19, p. 3421 - 3426]

39
[ 1132803-89-4 ]
[ 4119-41-9 ]
[ 1242640-64-7 ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: 2-mercapto-N-(thiophen-2-ylmethyl)nicotinamide With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1-iodo-3-phenylpropan In N,N-dimethyl-formamide at 20℃; for 72h;	227 mg (1.65 mmol) of K2CO3 were added to a solution of 375 mg (1.5 mmol) of 2-mercapto-N-(thiophen-2-ylmethyl)nicotinamide in DMF (3.5 ml), and stirring was carried out for 30 min at RT. 369 mg (1.5 mmol) of 1-iodo-3-phenylpropane were then added and stirring was carried out for a further 3 d at RT. The mixture was then concentrated in vacuo and the residue was taken up in an EA/water mixture. The organic phase was separated off and the aqueous phase was extracted again with EA. The combined organic phases were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by means of CC (EA/hex 1:1), yielding 382 mg (1.0 mmol, 69%) of 2-(3-phenyl-propylsulfanyl)-N-(thiophen-2-yl-methyl)-pyridine-3-carboxylic acid amide. MS: m/z 369.1 [M+H]+.

Reference： [1]Current Patent Assignee: Gruenenthal Pharma GmbH & Co. Kommanditgesellschaft - US2010/234429, 2010, A1 Location in patent: Page/Page column 21

40
[ 13329-40-3 ]
[ 4119-41-9 ]
[ 113138-08-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: 1-iodo-3-phenylpropan With indium; copper(ll) sulfate pentahydrate In tetrahydrofuran; water at 60℃; for 12h; Stage #2: 4-Iodoacetophenone With tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride In N,N-dimethyl acetamide; water at 80℃; for 24h;	General procedure for the synthesis of alkylindium compounds from alkyl iodidesand palladium-catalyzed cross-coupling reactions with aryl halides in aqueous media (Tables 3-4) General procedure: The insertion step 1: Alkyl iodide (1 mmol), indium (172.2 mg, 1.5 mmol), copper sulfate pentahydrate (25.0 mg, 0.1 mmol), and analytical grade THF (1.5 mL) and H2O (0.5 mL) were added in a flask equipped with a septum and a magnetic stir bar. The reaction mixture was vigorously stirred at 60 oC for 12 hrs. Then the upper clear solution was carefully separated from the bottom black precipitate by centrifugal. The remaining black precipitate was additionally stirred with THF(3 mL), and the THF layer was carefully separated from bottom precipitate by pipette. The combined organic layers were concentrated under vacuum. The crude mixture was directly used in the next step without further purification. The cross-coupling step 2: To the above residue was added aryl halide (0.7 mmol), LiCl (84.8 mg,2 mmol), Pd(PPh3)4 (57.8 mg, 0.05 mmol), DMA (1.5 mL), H2O (0.5 mL), and the reaction mixture was stirred at 80 oC for 24 hrs. Upon completion of the reaction, the reaction mixture was directly purified by flash silica gel column chromatography using petroleum ether/ethyl acetate as eluent toafford the pure products.
79%	Stage #1: 1-iodo-3-phenylpropan With indium In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; Stage #2: 4-Iodoacetophenone With tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride In N,N-dimethyl acetamide at 100℃;	5.1; 5.2 Example 5 Step 1: The alkyl iodide 1b-e (1 mmol),Indium powder (172.2mg, 1.5mmol),(25.4 mg, 0.1 mmol) and analytical grade THF (2 mL) were added to the reaction flask.Under argon protection,Heat to 60 ° C and stir for 24 hours.Filtered, added with tetrahydrofuran, filtered,Concentrated to obtain an alkyl indium metal complex.The crude mixture was used in the next step without further purification.Step 2: adding compound 2a to the above residue,P-acetyl iodobenzene (0.7 mmol), LiCl (84.8 mg,2mmol), Pd(PPh3)4 (57.8mg, 0.05mmol) and DMA (2mL), heated to 100 ° C to stir the reaction, TLC detection reactionAfter completion, the target product was purified by silica gel column chromatography, and the yields were calculated separately. The specific data are as follows.
76%	Stage #1: 1-iodo-3-phenylpropan With indium; copper(l) chloride In tetrahydrofuran at 20℃; for 24h; Stage #2: 4-Iodoacetophenone With bis-triphenylphosphine-palladium(II) chloride; lithium chloride In N,N-dimethyl acetamide at 100℃; for 24h;

Stage #1: 1-iodo-3-phenylpropan With indium; cobalt(II) bromide In tetrahydrofuran at 60℃; for 12h; Stage #2: 4-Iodoacetophenone With tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride In N,N-dimethyl acetamide at 100℃; for 24h;

Reference： [1]Wang, Peng; Chen, Bing-Zhi; Guo, Yi-Cong; Rao, Weidong; Shen, Zhi-Liang [Tetrahedron Letters, 2019, vol. 60, # 49]
[2]Current Patent Assignee: JINMING PHARMACEUTICAL; YANCHENG TEACHERS UNIVERSITY - CN109824495, 2019, A Location in patent: Paragraph 0089-0093
[3]Shen, Zhi-Liang; Goh, Kelvin Kau Kiat; Yang, Yong-Sheng; Lai, Yin-Chang; Wong, Colin Hong An; Cheong, Hao-Lun; Loh, Teck-Peng [Angewandte Chemie - International Edition, 2011, vol. 50, # 2, p. 511 - 514]
[4]Wang, Peng; Song, Xuan-Di; Chen, Bing-Zhi; Rao, Weidong; Shen, Zhi-Liang [Catalysis Communications, 2019, vol. 132]

41
[ 4119-41-9 ]
[ 1201598-11-9 ]
[ 1309198-93-3 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: C₅₉H₇₇N₃O₈ With sodium hydride In N,N-dimethyl-formamide for 0.5h; Stage #2: 1-iodo-3-phenylpropan In N,N-dimethyl-formamide	5.6.1. 4-O-Phenylpropyl-2,3,6-tri-O-benzyl-α-d-galactopyranosyl-(1,1)-(2S,3S,4R)-2-azido-3,4-di-O-benzyl-octadecan-1,3,4-triol (9) As shown in Scheme 5, a solution of alcohol 6 (126 mg, 0.13 mmol) in dry DMF (2 mL) was treated with 60% NaH (8 mg, 0.30 mmol) for 30 min. 3-Iodopropylbenzene (30 μL, 0.18 mmol) was added via syringe. The resulting mixture was stirred overnight. After diluted with ethyl acetate (10 mL), the mixture was washed twice with water and then brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography with hexane/ethyl acetate (15:1) to give 111 mg of product in 79% yield. 1H NMR (500 MHz, CDCl3) δ 7.39-7.17 (m, 30H), 4.94 (d, J = 3.3 Hz, 1H), 4.48 (d, J = 12.1 Hz, 1H), 4.81 (d, J = 12.1 Hz, 1H), 4.74-4.69 (m, 3H), 4.66 (d, J = 11.4 Hz, 1H), 4.61 (d, J = 11.5 Hz, 1H), 4.54 (d, J = 8.8 Hz, 1H), 4.51 (d, J = 8.5 Hz, 1H), 4.46 (d, J = 11.8 Hz, 1H), 4.06-4.02 (m, 2H), 4.01-3.92 (m, 3H), 3.83 (m, 1H), 3.78-3.75 (m, 3H), 3.70-3.64 (m, 2H), 3.56-3.50 (m, 2H), 2.67 (t, J = 7.7 Hz, 2H), 1.90 (m, 2H), 1.70 (m, 1H), 1.58 (m, 1H), 1.44 (m, 1H), 1.36-1.26 (m, 23H), 0.93 (t, J = 6.9 Hz, 3H); 13C NMR (125 MHz, CDCl3) δ 142.2, 138.83, 138.80, 138.5, 138.2, 138.0, 128.5, 128.41, 128.36, 128.30, 128.28, 128.25, 127.9, 127.8, 127.71, 127.68, 127.59, 127.50, 127.45, 127.41, 125.68, 98.8, 79.4, 79.0, 78.7, 76.3, 75.8, 73.7, 73.5, 73.3, 72.9, 72.7, 72.1, 69.7, 68.8, 68.5, 62.0, 32.4, 32.0, 31.9, 30.0, 29.8, 29.74, 29.69, 29.67, 29.65, 29.4, 25.5, 22.7, 14.1; HRMS calcd for C68H87N3O8Na ([M+Na]+) 1096.6385, found 1096.6369.

Reference： [1]Location in patent: experimental part Zhang, Wenpeng; Xia, Chengfeng; Nadas, Janos; Chen, Wenlan; Gu, Li; Wang, Peng George [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 8, p. 2767 - 2776]

42
[ 4119-41-9 ]
[ 73183-34-3 ]
[ 329685-40-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	With pyridine; C₅₀H₄₄CuN₄OP₂⁽¹⁺⁾*F₆P^(1-); N-ethyl-N,N-diisopropylamine In water monomer; acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;
73%	Stage #1: 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane With potassium ethanolate In i-Pr₂O at 20℃; for 1h; Inert atmosphere; Stage #2: 1-iodo-3-phenylpropan With 2,6-bis[(4R)-(+)-isopropyl-2-oxazolin-2-yl]pyridine; nickel(II) bromide 2-methoxyethyl ether complex In i-Pr₂O; Aminol at 20℃; for 3h; Inert atmosphere;
72%	With NiBr₂*diglyme; (R,R)-C₅H₃N(C₃H₃NO(CH(CH₃)2))2; KOCH₂CH₃ In di-isopropyl ether; N,N-dimethyl acetamide reaction of alkyl iodide with 1.4 equiv. of diboron compd. in presence of 5% bnickel compd., 6.6% pyridine deriv. and 1.3 equiv. of potassium ethylate in diisopropyl ether/dimethylacetamide at room temp.;

63%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tripotassium phosphate monohydrate; bis(1,1-dimethylethyl)methylphosphine tetrafluoroborate In water monomer; <i>tert</i>-butyl alcohol at 60℃; Inert atmosphere;
61%	With lithium tert-butylate In methanol; water monomer at 50℃; for 48h; Glovebox;	8 Example 8 In a glove box, t-BuOLi (1 mmol, 2 equivalents, 80.1 mg), B2pin2 (2 mmol, 4 equivalents, 507.9 mg), 0.85 mL of methanol solvent, 10 μL of H 2 O were added to the vial containing the stirrer in turn.3-iodopropylbenzene (0.5 mmol). The capped vial was removed from the glove box and the reaction mixture was stirred at 50 ° C for 48 hours. After cooling to room temperature, the reaction mixture was transferred to a 100 mL flask by methanol, and then a small amount of silica gel was added thereto. After removing the solvent in vacuo, the residue was poured onto a silica gel column.And purified by column chromatography,The developing solvent was a mixed solution of petroleum ether/ethyl acetate in a volume ratio of 30:1 to 20:1 to obtain a desired product, phenylpropylboronic acid pinacol ester, in a yield of 61%. When 3 equivalents of B2pin2 and 1.5 equivalents of t-BuOLi were used, the yield was 53%.
61%	With lithium tert-butylate In methanol; water monomer at 50℃; for 48h; Glovebox;
61%	With lithium tert-butylate In methanol; water monomer at 50℃;
35%	With 2,2':6,2''-terpyridine; bis[chlorido(η2,η2-cycloocta-1,5-diene)rhodium(I)]; sodium tertiary butoxide at 80℃; for 24h; Inert atmosphere;	2.1 General procedure for alkylboronic esters General procedure: In air, [Rh(COD)Cl]2 (2.5 mg, 0.005 mmol), terpyridine (2.73 mg, 0.01 mmol), t-BuONa (48 mg, 0.5 mmol), and bis(pinacolato)-diboron (95 mg, 0.375 mmol) were added to a Schlenk tube equipped with a stir bar. The vessel was evacuated and filled with argon (three cycles). t-AmylOH (1.0 mL) and alkyl chloride (0.25 mmol) were added sequentially under an argon atmosphere. The resulting reaction mixture was stirred vigorously at 80 °C for 24 h. Then water was added to the mixture at room temperature. The resulting mixture was extracted with ethyl acetate three times, and the combined organic phase was washed with water and brine and then dried over MgSO4. After filtration and evaporation of the solvent, the crude mixture was purified by column chromatography on silica gel with petroleum ether/ethyl acetate to give the target product.

Reference： [1]Nitelet, Antoine; Thevenet, Damien; Schiavi, Bruno; Hardouin, Christophe; Fournier, Jean; Tamion, Rodolphe; Pannecoucke, Xavier; Jubault, Philippe; Poisson, Thomas [Chemistry - A European Journal, 2019, vol. 25, # 13, p. 3262 - 3266]
[2]Dudnik, Alexander S.; Fu, Gregory C. [Journal of the American Chemical Society, 2012, vol. 134, # 25, p. 10693 - 10697]
[3]Dudnik, Alexander S.; Fu, Gregory C. [Journal of the American Chemical Society, 2012, vol. 134, # 25, p. 10693 - 10697]
[4]Location in patent: experimental part Joshi-Pangu, Amruta; Ma, Xinghua; Diane, Mohamed; Iqbal, Sidra; Kribs, Robert J.; Huang, Richard; Wang, Chao-Yuan; Biscoe, Mark R. [Journal of Organic Chemistry, 2012, vol. 77, # 15, p. 6629 - 6633]
[5]Current Patent Assignee: PEKING UNIVERSITY - CN109575063, 2019, A Location in patent: Paragraph 0047; 0048
[6]Liu, Qianyi; Hong, Junting; Sun, Beiqi; Bai, Guangcan; Li, Feng; Liu, Guoquan; Yang, Yang; Mo, Fanyang [Organic Letters, 2019]
[7]Liang, Hao; Liu, Qianyi; Mo, Fanyang; Qiu, Di; Yang, Jianxin; Yang, Yang; Yin, Yunxing; Zhang, Lei; Zhou, Shangyong [Organic Syntheses, 2022, vol. 99, p. 15 - 28]
[8]Gong, Tian-Jun; Jiang, Yuan-Ye; Fu, Yao [Chinese Chemical Letters, 2014, vol. 25, # 3, p. 397 - 400]

43
[ 41532-84-7 ]
[ 4119-41-9 ]
[ 1388714-11-1 ]

Yield	Reaction Conditions	Operation in experiment
81%	In acetonitrile for 24h; Reflux;	4.8. General synthesis of indolium and benz[e]indolium salts 16-21 General procedure: A mixture of indolenine 14 or 15 (31.4 mmol) and alkyl halide (94.2 mmol) were refluxed in acetonitrile (25 mL) for 24 h. The solvent was concentrated and removed in vacuo to afford an oil residue. The reaction mixture was cooled in an ice bath and solid was obtained upon addition of ether and acetone. The resulting crystals were filtered and dried to yield red to light pink solid which was used without further purification in subsequent reactions.
	In acetonitrile Reflux;
	In acetonitrile at 85℃;

Reference： [1]Location in patent: experimental part Sinha, Sarmistha Halder; Owens, Eric A.; Feng, You; Yang, Yutao; Xie, Yan; Tu, Yaping; Henary, Maged; Zheng, Yujun George [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 647 - 659]
[2]Owens, Eric A.; Hyun, Hoon; Tawney, Joseph G.; Choi, Hak Soo; Henary, Maged [Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4348 - 4356]
[3]St. Lorenz, Anna; Buabeng, Emmanuel Ramsey; Taratula, Oleh; Taratula, Olena; Henary, Maged [Journal of Medicinal Chemistry, 2021, vol. 64, # 12, p. 8798 - 8805]

44
[ 4119-41-9 ]
5-(benzo[c,d]indol-2(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione [ No CAS ]
[ 1320334-80-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 18h; Inert atmosphere;	4.5. General procedures of the synthesis of compounds 5-7 General procedure: A mixture of compound 4 (10.2 mmol), alkyl iodide (30.6 mmol) and K2CO3 (30.6 mmol) were heated in DMF (40 mL) at 90 °C for 18 h under a nitrogen atmosphere. The mixture was cooled to room temperature and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified on silica gel (flash column chromatography, using EtOAc-hexanes, 1:2 as an eluent).
80%	With potassium carbonate In N,N-dimethyl-formamide

Reference： [1]Location in patent: experimental part Sinha, Sarmistha Halder; Owens, Eric A.; Feng, You; Yang, Yutao; Xie, Yan; Tu, Yaping; Henary, Maged; Zheng, Yujun George [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 647 - 659]
[2]Current Patent Assignee: UNIVERSITY SYSTEM OF GEORGIA - WO2016/25620, 2016, A1 Location in patent: Page/Page column 28

45
[ 27126-20-1 ]
[ 4119-41-9 ]

Yield	Reaction Conditions	Operation in experiment
56%	With tert-Butyl iodide In dichloromethane at 20℃; for 18h; Inert atmosphere;	4.3 General procedure for the conversion of azides into iodides General procedure: To a solution of alkyl azide (1 equiv) 0.2 M in dichloromethane were added at room temperature 2-4 equiv of tert-BuI under an argon atmosphere. After stirring for 18 h at room temperature, the reaction mixture was washed with saturated Na2S2O4 and the layers were separated. The organic phase was dried (MgSO4), filtered, and concentrated in vacuo. Flash column chromatography on silica gel using pentane as the eluent afforded the corresponding iodide.

Reference： [1]Maury, Julien; Feray, Laurence; Bertrand, Michele P.; Kapat, Ajoy; Renaud, Philippe [Tetrahedron, 2012, vol. 68, # 47, p. 9606 - 9611,6]

46
[ 4119-41-9 ]
[ 929626-16-4 ]
[ 1442416-10-5 ]

Yield	Reaction Conditions	Operation in experiment
216 mg	With nickel(II) bromide dimethoxyethane; potassium <i>tert</i>-butylate; trans-N,N'-dimethylcyclohexane-1,2-diamine; iso-butanol In 1,4-dioxane at 60℃; for 15h; Inert atmosphere; Glovebox;

Reference： [1]Robbins, Daniel W.; Hartwig, John F. [Angewandte Chemie - International Edition, 2013, vol. 52, # 3, p. 933 - 937][Angew. Chem., 2012, vol. 125, # 3, p. 967 - 971,5]

47
[ 4119-41-9 ]
[ 479411-93-3 ]
[ 1442416-12-7 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 933 - 937
Angew. Chem.,2012,vol. 125,p. 967 - 971,5

48
[ 4119-41-9 ]
[ 401797-04-4 ]
[ 1442416-11-6 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 933 - 937
Angew. Chem.,2012,vol. 125,p. 967 - 971,5

49
[ 214360-67-5 ]
[ 4119-41-9 ]
[ 175465-12-0 ]

Yield	Reaction Conditions	Operation in experiment
143 mg	With nickel(II) bromide dimethoxyethane; potassium <i>tert</i>-butylate; trans-N,N'-dimethylcyclohexane-1,2-diamine; iso-butanol In 1,4-dioxane at 60℃; for 15h; Inert atmosphere; Glovebox;

Reference： [1]Robbins, Daniel W.; Hartwig, John F. [Angewandte Chemie - International Edition, 2013, vol. 52, # 3, p. 933 - 937][Angew. Chem., 2012, vol. 125, # 3, p. 967 - 971,5]

50
[ 4119-41-9 ]
[ 1212021-11-8 ]
[ 1442416-13-8 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 933 - 937
Angew. Chem.,2012,vol. 125,p. 967 - 971,5

51
[ 4119-41-9 ]
[ 402503-13-3 ]
[ 1034519-10-2 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 933 - 937
Angew. Chem.,2012,vol. 125,p. 967 - 971,5

52
[ 4119-41-9 ]
[ 1451061-31-6 ]
[ 1451061-24-7 ]

Yield	Reaction Conditions	Operation in experiment
32%	Stage #1: (S)-1-(4-fluorophenyl)-4-(trifluoromethyl)azetidin-2-one With lithium hexamethyldisilazane In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #3: 1-iodo-3-phenylpropan In tetrahydrofuran; hexane at -78℃; for 4h; Inert atmosphere;	General procedure: A dry three-necked flask chargedwith 7a (70 mg,0.3 mmol) was dissolved in anhydrous tetrahydrofuran (2 ml) under an nitrogen atmosphereand cooled to -78 . LHMDS(0.39 mmol.,1M in hexane) dissolved in anhydrous tetrahydrofuran (2 ml) was then addeddropwise, and stirred at -78 for 30min. The solution of lithium enolate was treated with distilledhexamethylphosphoramide (0.33 ml, 2.16 mmol), which was further stirred at -78 for 30 min. Then, electrophile 8a(1.2 mmol, 295mg) was added dropwise to the reaction mixture. After stirring at-78 for 4 h. The reaction mixture wasquenched with sat. NH4Cl solution, extracted with EtOAc (3 × 8 mL).The combined organic phases were washed with brine (20 mL), drying overanhydrous MgSO4, filtration, and concentration in vacuo. The crudeproduct protected by TBDMS was purified by Column chromatography on silica gel and dissolved in anhydrous THF (4.0mL), anhydrous pyridine (0.8 mL) followed by HF.pyridine complex (0.8 mL) wereadded and the solution was stirred for 16 h. To the reaction mixture was addedethyl ether (10 mL). Sat. aq. NaHCO3 (5 mL) was added and the extractedwith EtOAc (3 × 8 mL). The combined organic phases were washed with brine (10mL), drying over anhydrous MgSO4, filtration, and concentration invacuo. The crude product was further purified by Column chromatography (petroleum ether : ethyl acetate = 16:1) on silica gel togive a pure product 1a.

Reference： [1]Liu, Yingle; Chen, Jun-Ling; Wang, Gai-Hong; Sun, Peng; Huang, Heyao; Qing, Feng-Ling [Tetrahedron Letters, 2013, vol. 54, # 40, p. 5541 - 5543]

53
[ 4119-41-9 ]
[ 1453252-01-1 ]
[ 1451061-23-6 ]

Yield	Reaction Conditions	Operation in experiment
32%	Stage #1: (S)-1-(4-methoxyphenyl)-4-(trifluoromethyl)azetidin-2-one With lithium hexamethyldisilazane In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #3: 1-iodo-3-phenylpropan In tetrahydrofuran; hexane at -78℃; for 4h; Inert atmosphere;	General procedure: A dry three-necked flask chargedwith 7a (70 mg,0.3 mmol) was dissolved in anhydrous tetrahydrofuran (2 ml) under an nitrogen atmosphereand cooled to -78 . LHMDS(0.39 mmol.,1M in hexane) dissolved in anhydrous tetrahydrofuran (2 ml) was then addeddropwise, and stirred at -78 for 30min. The solution of lithium enolate was treated with distilledhexamethylphosphoramide (0.33 ml, 2.16 mmol), which was further stirred at -78 for 30 min. Then, electrophile 8a(1.2 mmol, 295mg) was added dropwise to the reaction mixture. After stirring at-78 for 4 h. The reaction mixture wasquenched with sat. NH4Cl solution, extracted with EtOAc (3 × 8 mL).The combined organic phases were washed with brine (20 mL), drying overanhydrous MgSO4, filtration, and concentration in vacuo. The crudeproduct protected by TBDMS was purified by Column chromatography on silica gel and dissolved in anhydrous THF (4.0mL), anhydrous pyridine (0.8 mL) followed by HF.pyridine complex (0.8 mL) wereadded and the solution was stirred for 16 h. To the reaction mixture was addedethyl ether (10 mL). Sat. aq. NaHCO3 (5 mL) was added and the extractedwith EtOAc (3 × 8 mL). The combined organic phases were washed with brine (10mL), drying over anhydrous MgSO4, filtration, and concentration invacuo. The crude product was further purified by Column chromatography (petroleum ether : ethyl acetate = 16:1) on silica gel togive a pure product 1a.

Reference： [1]Liu, Yingle; Chen, Jun-Ling; Wang, Gai-Hong; Sun, Peng; Huang, Heyao; Qing, Feng-Ling [Tetrahedron Letters, 2013, vol. 54, # 40, p. 5541 - 5543]

54
[ 2038-62-2 ]
[ 4119-41-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	With YbI₃ In dichloromethane at 20℃; for 15h;
95 %Chromat.	With trimethylsilyl iodide; YbI₃(tetrahydrofuran)3 In dichloromethane at 20℃; for 8h; Glovebox;
	With trimethylsilyl iodide; tris(pentafluorophenyl)borate In 1,2-dichloro-ethane at 20℃; for 12h; Glovebox; Schlenk technique;

Reference： [1]Traeff, Annika M.; Janjetovic, Mario; Ta, Linda; Hilmersson, Goeran [Angewandte Chemie - International Edition, 2013, vol. 52, # 46, p. 12073 - 12076][Angew. Chem., 2013, vol. 52-125, # 46, p. 12295 - 12298]
[2]Janjetovic, Mario; Ekebergh, Andreas; Träff, Annika M.; Hilmersson, Göran [Organic Letters, 2016, vol. 18, # 12, p. 2804 - 2807]
[3]Jaiswal, Amit K.; Prasad, Pragati K.; Young, Rowan D. [Chemistry - A European Journal, 2019, vol. 25, # 25, p. 6290 - 6294]

55
[ 4119-41-9 ]
[ 104-52-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	With 1,10-Phenanthroline; iron(II) chloride; In acetonitrile; at 60℃; for 0.5h;	General procedure: To a solution of iodoalkane (1a) (0.12 mmol,1.0 equiv) in CH3CN (1.2 mL) was added FeCl2 (0.12 mmol,1.0 equiv) and 1,10-phenanthroline monohydrate (0.36 mmol,3.0 equiv). After being stirred at 60 C for 0.5 h, solvent evaporation and silica gel column chromatography afforded N-(2-chloroethyl)-4-methylbenze-nesulfonamide (2a).

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 10642 - 10650
[2]Bulletin of the Korean Chemical Society,2018,vol. 39,p. 695 - 698

56
[ 4119-41-9 ]
[ 104863-67-4 ]
[ 85674-68-6 ]

Reference： [1]ChemMedChem,2014,vol. 9,p. 614 - 626

57
[ 4119-41-9 ]
[ 100-58-3 ]
[ 1081-75-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With copper(l) iodide; lithium chloride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	Representative Procedure for the CuI-Catalyzed Cross-Coupling Reaction General procedure: A flask charged with LiCl (67 mg, 1.60 mmol) was heated in vacuo and flushed with argon. To the flask were added PhMgBr (2a, 1.28 mL, 0.94 M in THF, 1.20 mmol), 1a (0.12 mL, 0.80 mmol), and CuI (45 mg, 0.24 mmol) sequentially. The mixture was stirred at room temperature for 2 h and diluted with saturated NH4Cl. The resulting mixture was extracted with EtOAc four times. The combined extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (hexane) to afford 3a (130 mg, 83%).

Reference： [1]Nakata, Kenya; Feng, Chao; Tojo, Toshifumi; Kobayashi, Yuichi [Tetrahedron Letters, 2014, vol. 55, # 42, p. 5774 - 5777]

58
[ 4119-41-9 ]
2,2'-(ethane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) [ No CAS ]
[ 1357000-41-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: 2,2'-(ethane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) With copper(l) iodide; lithium tert-butoxide In N,N-dimethyl-formamide at 20 - 60℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: 1-iodo-3-phenylpropan In N,N-dimethyl-formamide at 60℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Zhang, Zhen-Qi; Yang, Chu-Ting; Liang, Lu-Jun; Xiao, Bin; Lu, Xi; Liu, Jing-Hui; Sun, Yan-Yan; Marder, Todd B.; Fu, Yao [Organic Letters, 2014, vol. 16, # 24, p. 6342 - 6345]

59
[ 4119-41-9 ]
[ 121-69-7 ]
N,N-dimethyl-N-(3-phenylpropyl)anilinium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	In acetonitrile at 70℃; for 28.5h;	General procedure: The new cholinesterase inhibitors (1-19; Figs. 2 and 3)were prepared via developed synthetic strategy [17-19]. Thesolution of amine/pyridine (5 mmol) and corresponding alkylatingagent (8 mmol) in MeCN (10 ml) was stirred at 70°C. The reaction mixture was cooled to the room temperatureand it was portioned with acetone (50 ml) and cooled in refrigerator(5°C) overnight. The crystalline or amorphouscrude product was collected by filtration, washed with acetone(320 ml) and crystalized from acetone. NMR, ESI-MSand elemental analysis determined the entity and purity of allprepared compounds

Reference： [1]Benek, Ondrej; Musilek, Kamil; Horova, Anna; Dohnal, Vlastimil; Dolezal, Rafael; Kuca, Kamil [Medicinal Chemistry, 2015, vol. 11, # 1, p. 21 - 29]

60
[ 103-83-3 ]
[ 4119-41-9 ]
N-benzyl-N,N-dimethyl-3-phenylpropyl-1-ammonium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In acetonitrile at 70℃; for 8h;	General procedure: The new cholinesterase inhibitors (1-19; Figs. 2 and 3)were prepared via developed synthetic strategy [17-19]. Thesolution of amine/pyridine (5 mmol) and corresponding alkylatingagent (8 mmol) in MeCN (10 ml) was stirred at 70°C. The reaction mixture was cooled to the room temperatureand it was portioned with acetone (50 ml) and cooled in refrigerator(5°C) overnight. The crystalline or amorphouscrude product was collected by filtration, washed with acetone(320 ml) and crystalized from acetone. NMR, ESI-MSand elemental analysis determined the entity and purity of allprepared compounds

Reference： [1]Benek, Ondrej; Musilek, Kamil; Horova, Anna; Dohnal, Vlastimil; Dolezal, Rafael; Kuca, Kamil [Medicinal Chemistry, 2015, vol. 11, # 1, p. 21 - 29]

61
[ 4119-41-9 ]
[ 655-48-1 ]
(±)-(4RS,5RS)-4,5-diphenyl-3-phenpropyl-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-iodo-3-phenylpropan With iodine; magnesium In tetrahydrofuran for 3h; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran; diethyl ether at -78 - -40℃; for 4h; Inert atmosphere; Stage #3: DL-1,2-diphenylethane-1,2-diol In tetrahydrofuran; diethyl ether at -40 - 20℃; for 16h; Inert atmosphere;	(±)-(4R,5R)-4,5-Diphenyl-2-phenethyl-1,3,2-dioxaborolane (13a) General procedure: (I) Preparation ofphenylethylmagnesium bromide: A stirred mixture of magnesium metal (9.90 g, 413 mmol,mechanically activated under Ar before hand) and iodine (22 mg, 0.09 mmol) in anhydrous THF(100 mL) at rt under Ar was treated with neat 2-phenethyl bromide (27.3 mL, d = 1.355, 37.0 g, 200mmol) at such a rate that an exotherm was initiated and sustained to maintain a gentle reflux. Themixture turned black and returned to rt as the alkyl halide was consumed and the Grignard reagentwas formed. The titer for the solution of Grignard reagent generated was determined to be 2.03 M(by measuring the amount of BnOH required to quench the charge-transfer complex formed fromtrace 1,10-phenanthroline and a known volume of Grignard reagent solution) and a total volume of89 mL was recovered (181 mmol, 91%). (II) Generation of boronate: A stirred solution of a portionof the Grignard reagent prepared above (4.00 mL, 2.03 M in THF, 8.12 mmol) in anhydrous Et2O(20 mL) at -78 °C under Ar was treated dropwise with triisopropyl borate (1.87 mL, d = 0.818, 1.53g, 8.14 mmol). The resulting mixture was allowed to warm to -40 °C during 4 h and then treatedwith (±)-syn-1,2-diphenylethan-1,2-diol (23, 0.871 g, 4.07 mmol) in one portion. The mixture wasallowed to warm slowly to rt and stirred for a total of 16 h before being quenched with sat. aq.NH4Cl (20 mL). EtOAc (20 mL) was added and the layers shaken and separated. The aqueous phasewas extracted with EtOAc (3x15 mL) and the combined organic phases were washed with H2O (20mL), brine (20 mL), dried (Na2SO4) and concentrated in vacuo. The residue was purified by columnchromatography (SiO2, eluting with 30% EtOAc in hexanes) to afford the racemic boronate (±)-13a(1.01 g, 3.08 mmol, 76%) as a pale yellow oil: IR (neat) 3429, 2095, 1638, 1384, 1020, 756, 697cm-1; 1H NMR (400 MHz, CDCl3) δ 7.38-7.30 (11H, m), 7.22-7.18 (4H, m), 5.12 (2H, s), 2.93 (2H,t, J = 8.0 Hz), 1.46 (2H, dd, J = 8.6, 7.5 Hz) ppm; 13C NMR (100 MHz, CDCl3) δ 144.3 (0), 140.5(2C, 0), x15 C cluster within [129.0 (1), 128.6 (1), 128.5 (1), 128.3 (1), 125.91 (1), 128.9 (1)], 86.6(2C, 1), 30.2 (2) ppm [BnCH2B(OR)2 not observed]; MS (EI+) m/z 328 (M+•, 60%), 237 (20), 210(50), 180 (100); HRMS (EI+) m/z = 328.1621 (calcd. for C22H21BO2: 328.1635

Reference： [1]Hoyt, Amanda L.; Blakemore, Paul R. [Tetrahedron Letters, 2015, vol. 56, # 23, p. 2980 - 2982]

62
[ 4119-41-9 ]
[ 72824-04-5 ]
[ 1588-44-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With copper(l) iodide; lithium tert-butoxide In N,N-dimethyl-formamide at 60℃; for 24h; Inert atmosphere;

Reference： [1]Wang, Guang-Zu; Jiang, Jian; Bu, Xiao-Song; Dai, Jian-Jun; Xu, Jun; Fu, Yao; Xu, Hua-Jian [Organic Letters, 2015, vol. 17, # 15, p. 3682 - 3685]

63
[ 4119-41-9 ]
[ 38841-98-4 ]
[ 6742-54-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	With [(TMEDA)Ni(Br)(2-(1-pyrrolidinyl)phenol)] In tetrahydrofuran at 20℃; for 2h;	3.7. Typical Procedure for the Kumada Cross-Coupling Reactions in Table 1 General procedure: A vial was charged with alkyl halide substrate (0.2 mmol) and nickel catalyst (3 mol %), and theinternal standard undecane (0.2 mmol) in THF (3 mL). OctylMgCl (0.24 mmol, 2 M in THF) was thenadded dropwise at room temperature. The resulting solution was stirred at room temperature for 2 h.The reaction mixture was then filtered through a plug of silica gel and analyzed by gaschromatography. The response factor of ethyl undecanoate calibrated to the internal standard was usedto calculate product yields.

Reference： [1]Yu, Siqi; Wang, Huan; Sledziewski, Jill E.; Madhira, Venkata N.; Takahashi, Cyrus G.; Leon, Michelle K.; Dudkina, Yulia B.; Budnikova, Yulia H.; Vicic, David A. [Molecules, 2014, vol. 19, # 9, p. 13603 - 13613]

64
[ 4119-41-9 ]
t-butyl 3-oxo-4-(phenylsulfonyl)-2-(triphenyl-λ⁵-phosphanylidene)butanoate [ No CAS ]
C₄₁H₄₁O₅PS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: t-butyl 3-oxo-4-(phenylsulfonyl)-2-(triphenyl-λ⁵-phosphanylidene)butanoate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.666667h; Inert atmosphere; Stage #2: 1-iodo-3-phenylpropan In tetrahydrofuran; mineral oil at 0 - 20℃; for 13h; Inert atmosphere;	Typical procedures for the alkylation of 4 to 5a General procedure: NaH (10.4 mg, 1.3 eq) was added to a stirred solution of 4 (111.7mg, 0.20 mmol) in dry THF (10 mL), and the resulting slurrywas stirred at rt for 40 min under Ar. To this was addedbenzyl bromide (30.9 mL, 1.3 eq) by syringe, and the resultingmixture was stirred at rt for 24 h under Ar. The reactionmixture was quenched with CH2Cl2 (20 mL) and water (10 mL),and the organic layer was separated. The aqueous layer wasextracted with CH2Cl2 (10 mL × 2), and the combined organiclayers were dried over MgSO4, filtered, and concentrated.The residue was purified by flash chromatography (SiO2,CH2Cl2/EtOAc = 10/1) to furnish 5a (121.3 mg, 94%) as awhite solid.

Reference： [1]Lee, Kieseung [Journal of the Korean Chemical Society, 2015, vol. 59, # 6, p. 537 - 540]

65
[ 4119-41-9 ]
[ 184906-29-4 ]
5-methoxy-3,3-dimethyl-2-(3-phenylpropyl)isoindolin-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
850 mg	Stage #1: 5-methoxy-3,3-dimethylisoindolin-1-one With sodium hydride In N,N-dimethyl-formamide at 80℃; for 1h; Stage #2: 1-iodo-3-phenylpropan With sodium hydride In N,N-dimethyl-formamide	330B Preparation 33 OB: 5 -methoxy-3 ,3 -dimethyl-2-(3 -phenylpropyl)isoindolin- 1-one To a mixture of 5 -methoxy-3 ,3 -dimethylisoindolin- 1-one (1 .8 g, 9.41 mmol) inDMF (50 mL) was added sodium hydride (0.565 g, 14.12 mmol) portionwise. Afteraddition, the reaction mixture was heated to 80 °C for 1 hour followed by the addition of3-iodopropyl)benzene (3.03 mL, 18.83 mmol). Reaction was incomplete after 2 hours.Additional sodium hydride (0.5 65 g, 14.12 mmol) was added and the reaction mixturewas heated overnight. Reaction was still incomplete. Additional sodium hydride (0.565 g, 14.12 mmol) was added and heating was continued for 4 more hours. The reaction mixture was diluted with ethyl acetate and washed twice with saturated NaC1. The organic layer was dried with MgSO4, filtered and concentrated. The crude material was purified on a silica gel cartridge (40 g) using an EtOAc/Hex gradient (0-100% EtOAc over 13 CV) to afford 850 mg of 5 -methoxy-3 ,3 -dimethyl-2-(3 -phenylpropyl)isoindolin1-one. HPLC retention time = 1.00 mm (condition G); LC/MS M’ = 310; ‘H NMR (400MHz, CHLOROFORM-d) ö 7.75 (d, J=8.4 Hz, 1H), 7.46-7.14 (m, 5H), 6.96 (dd, J8.4, 2.2 Hz, 1H), 6.86 (d, J2.0 Hz, 1H), 3.90 (s, 3H), 2.75 (td, J=7.8, 5.4 Hz, 2H), 2.16-2.02 (m, 2H), 2.00-1.86 (m, 2H), 1.60 (s, 3H), 1.46 (s, 3H). MS (m+1) = 310.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2016/28959, 2016, A1 Location in patent: Page/Page column 170; 172

66
[ 1821-12-1 ]
[ 4119-41-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With N-iodo-succinimide; iodine In 1,2-dichloro-ethane at 100℃; for 8h; Sealed tube; Darkness;
90%	With N-iodo-succinimide; iodine In 1,2-dichloro-ethane at 100℃; for 8h; Darkness;
	Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C 2: 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; sodium iodide; 2,4,6-trimethyl-pyridine / acetone / 45 °C / Irradiation; Inert atmosphere

Reference： [1]Nakai, Yuhta; Moriyama, Katsuhiko; Togo, Hideo [European Journal of Organic Chemistry, 2016, vol. 2016, # 4, p. 768 - 772]
[2]Lv, Honggui; Xiao, Li-Jun; Zhao, Dongbing; Zhou, Qi-Lin [Chemical Science, 2018, vol. 9, # 33, p. 6839 - 6843]
[3]Chen, Kun-Quan; Wang, Zhi-Xiang; Chen, Xiang-Yu [Organic Letters, 2020, vol. 22, # 20, p. 8059 - 8064]

67
[ 4119-41-9 ]
[ 111-64-8 ]
p-octanoyl iodopropylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With aluminum (III) chloride at -5℃;	3 Preparation of octanoyl iodopropylbenzene (Compound III) Aluminum chloride (5.3 g, 0.04 mol, 2 q) was added to a 50 ml three-necked flask, and the pre-mixed 3-iodophenyl propane (5 g) was added dropwise while maintaining the temperature of the reaction solution at a temperature not higher than -15 ° C , 0.02 mol, 1 eq) and n-octanoyl chloride (3.9 g, 0.024 mol, 1.2 eq). After completion of the dropwise addition, the reaction was complete at -5 ° C until the reaction was complete [reaction takes about 2-4 hours, HPLC detection: 0.5% raw material 3-iodophenylpropane]. The reaction mixture was slowly poured into 50 ml of 5% hydrochloric acid and extracted with ethyl acetate (20 ml x 3 times). The organic layers were combined and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate ( 3g) was dried and filtered, and the filtrate was concentrated at about no more than 40 ° C to give octanoyliodopropylbenzene (6.8 g, HPLC 96.26% yield 92%)

Reference： [1]Current Patent Assignee: CHENGDU HONGDA PHARMACEUTICAL CO LTD - CN103804123, 2016, B Location in patent: Paragraph 0071-0072

68
[ 4119-41-9 ]
[ 106-95-6 ]
[ 1588-44-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With palladium diacetate; copper(II) acetate monohydrate; ammonium bromide; lithium chloride In water; N,N-dimethyl-formamide at 0℃; for 12h; Electrochemical reaction;

Reference： [1]Lai, Yin-Long; Huang, Jing-Mei [Organic Letters, 2017, vol. 19, # 8, p. 2022 - 2025]

69
[ 4119-41-9 ]
[ 1266570-74-4 ]
C₃₃H₃₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With 1,3-bis(tert-butyl)ylimidazolinium chloride; palladium diacetate; caesium carbonate In acetonitrile at 90℃; Inert atmosphere; Sealed tube;	Synthesis of C-H alkylation products (2) To a 10 ml oven-dried microwave vial that contained a magnetic stirring bar was added anhydrous Cs2CO3 (488.7 mg, 1.5 mmol), and the vial was then dried under vacuum with a heating gun for about two minutes. After cooling to room temperature, Pd(OAc)2 (6.7 mg, 0.03 mmol), L7 (6.6 mg, 0.03 mmol) and 1 (if solid) (0.3 mmol) were added to the vial sequentially. The vial was then sealed with a resealable silicone/PTFE crimp cap, followed by three evacuation/Ar backfill cycles. After that, CH3CN or iPrCN (3 ml) and alkylating reagent 5 were added sequentially to the vial via the cap using a syringe under argon (if substrate 1 was a liquid, it was dissolved in the solvent and added to the vial using a syringe). The vial was degassed through three freeze-pump-thaw cycles before placing in a preheated oil bath at 90 °C. After the reaction was complete, as monitored by TLC, the reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate and filtered through a short pad of Celite by eluting with ethyl acetate. After evaporation, the residue was purified by chromatography on silica gel to afford the desired product 2.

Reference： [1]Ye, Juntao; Shi, Zhihao; Sperger, Theresa; Yasukawa, Yoshifumi; Kingston, Cian; Schoenebeck, Franziska; Lautens, Mark [Nature Chemistry, 2017, vol. 9, # 4, p. 361 - 368]

70
[ 4119-41-9 ]
[ 171800-72-9 ]
[ 1208109-81-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: (2RS)-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride With sodium hydride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1-iodo-3-phenylpropan In N,N-dimethyl-formamide at 120℃; for 5h; Stage #3: With hydrogenchloride In diethyl ether; water; ethyl acetate Cooling with ice;	26 5.1.26. 6-Methoxy-1'-(3-phenylpropyl)-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride (3f) A mixture of 8d hydrochloride (0.30 g, 1.06 mmol), N-ethyldiisopropylamine(0.68 g, 5.3 mmol) and sodium hydride (0.15 g,3.7 mmol) in DMF (10 mL) was stirred for 0.5 h at rt. To the mixturewas added 1-iodo-3-phenylpropane (0.86 g, 3.5 mmol) in anice-bath, and the mixture was stirred for 5 h at 120 C. The mixturewas partitioned between ethyl acetate and water, and the aqueouslayer was extracted with ethyl acetate. The combined organic layerwas washed with brine, dried (Na2SO4) and concentrated in vacuo.The residue was purified by column chromatography on basic silicagel (n-hexane/EtOAc = 10/1-5/1) to produce pale brown oils, to asolution of which in ether (5 mL) was added 4 N HCl/EtOAc(0.30 mL, 1.2 mmol) dropwise in an ice-bath, and the precipitationwas filtered off to obtain 3f (0.32 g, 76%) as white crystals: 1H NMR(DMSO-d6) d 1.40-2.75 (12H, m), 2.80-3.60 (6H, m), 3.87 (3H, s),6.98-7.02 (2H, m), 7.16-7.37 (5H, m), 7.95 (1H, d, J = 8.4 Hz),9.59 (1H, brs); Anal. Calcd for C24H29NOHCl0.5H2O: C, 70.49; H,7.64; N, 3.42. Found: C, 70.53; H, 7.86; N, 3.32; LC/MS (ESI) m/z364 (M+H)+.

Reference： [1]Imaeda, Toshihiro; Ono, Koji; Nakai, Kazuo; Hori, Yasunobu; Matsukawa, Jun; Takagi, Terufumi; Fujioka, Yasushi; Tarui, Naoki; Kondo, Mitsuyo; Imanishi, Akio; Inatomi, Nobuhiro; Kajino, Masahiro; Itoh, Fumio; Nishida, Haruyuki [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 14, p. 3719 - 3735]

71
[ 2832-16-8 ]
[ 4119-41-9 ]
C₁₅H₂₁NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With (2,9-dimethyl-4,7-diphenyl-1,10-phenantroline)NiBr₂; potassium <i>tert</i>-butylate; diethylzinc In 1,4-dioxane; tert-butyl methyl ether at 40℃; for 22h; Inert atmosphere; Sealed tube; Glovebox;

Reference： [1]Rezazadeh, Sina; Devannah, Vijayarajan; Watson, Donald A. [Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8110 - 8113]

72
[ 4119-41-9 ]
[ 34226-11-4 ]
(E)-1,1-dimethyl-2-(1,1,1-trifluoro-6-phenylhexan-2-ylidene)hydrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: (E)-1,1-dimethyl-2-(1,1,1-trifluoropropan-2-ylidene)hydrazine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Stage #2: 1-iodo-3-phenylpropan In tetrahydrofuran; hexane at -78 - 0℃; for 1h; diastereoselective reaction;	General procedure for the alkylation/addition reactions with 1 (E)-1,1-Dimethyl-2-(1,1,1-trifluoro-6-phenylhexan-2-ylidene)hydrazine (7b). A solution of (E)-1,1-dimethyl-2-(1,1,1-trifluoropropan-2-ylidene)hydrazine 1 (0.4 g, 2.60 mmol) in THF (6 mL) was cooled in a dryice/acetone bath for 15 minutes. Next, n-butyl lithium, as a solution in hexanes (1.6 M), (1.62 mL, 2.60 mmol) was added slowly and the solution was stirred 45 minutes at -78 °C before (3-iodopropyl)benzene 6b (0.209 mL,1.30 mmol) was added. After stirring 5 minutes, the reaction was transferred to an ice water bath. After 1 hour,the reaction was quenched with a saturated ammonium chloride aqueous solution and diluted with water andEtOAc. The layers were separated and the aqueous layer extracted twice with EtOAc. The combined organics arewashed with 50% saturated ammonium chloride aqueous solution, brine, dried over sodium sulfate, filtered and concentrated. Silica chromatography (gradient 0% to 50% DCM in Heptane) gave 7b (0.308 g, 87 % yield) as clear oil.

Reference： [1]Judd, Ted C.; Brown, Derek B. [Tetrahedron Letters, 2017, vol. 58, # 47, p. 4455 - 4458]

73
[ 4119-41-9 ]
bis-(4-methoxyphenyl)manganese [ No CAS ]
[ 40715-68-2 ]

Yield	Reaction Conditions	Operation in experiment
46%	With iron(II) chloride In tetrahydrofuran at -20 - 25℃; for 16h; Inert atmosphere; Schlenk technique;	Typical Procedure 4 (TP4): Iron-catalyzed cross-coupling of di(hetero)arylmanganese reagents withalkyl halides General procedure: A dry and argon-flushed 20 mL Schlenk tube, equipped with a stirring bar and a septum, was charged withanhydrous FeCl2 (25 mg, 0.20 mmol, 20 mol%). The alkyl halide (1 mmol, 1.0 equiv) and THF (1 mL) were addedand the mixture was cooled to -20 °C. The di(hetero)arylmanganese reagent (0.7 mmol, 0.7 equiv) was addeddropwise and the mixture was allowed to warm to room temperature overnight. A sat. aq. solution of NH4Cl(5 mL) and EtOAc (5 mL) were added, the phases were separated and the aqueous phase was extracted withEtOAc (3 x 20 mL). The combined organic phases were washed with brine, dried over Na2SO4 and the solventswere evaporated. The residue was subjected to column chromatography purification (SiO2; i-hexane/EtOAc)yielding the corresponding title compound.

Reference： [1]Hofmayer, Maximilian S.; Hammann, Jeffrey M.; Cahiez, Gérard; Knochel, Paul [Synlett, 2018, vol. 29, # 1, p. 65 - 70]

74
[ 519054-55-8 ]
[ 4119-41-9 ]
[ 917-57-7 ]
(S)-2-(1-(benzofuran-5-yl)-5-phenylpentyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]