[ CAS No. 25309-64-2 ] {[proInfo.proName]}

Name: 25309-64-2|1-Ethyl-4-iodobenzene|96%
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Quality Control of [ 25309-64-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 25309-64-2 ]

Product Details of [ 25309-64-2 ]

CAS No. :	25309-64-2	MDL No. :	MFCD00060663
Formula :	C₈H₉I	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OOLSRHZMXAYDFB-UHFFFAOYSA-N
M.W :	232.06	Pubchem ID :	141189
Synonyms :

Calculated chemistry of [ 25309-64-2 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.93
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.93 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.45
Log Po/w (XLOGP3) :	3.92
Log Po/w (WLOGP) :	2.85
Log Po/w (MLOGP) :	3.83
Log Po/w (SILICOS-IT) :	3.61
Consensus Log Po/w :	3.33

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.18
Solubility :	0.0155 mg/ml ; 0.0000667 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.62
Solubility :	0.0558 mg/ml ; 0.00024 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.15
Solubility :	0.0166 mg/ml ; 0.0000714 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.6

Safety of [ 25309-64-2 ]

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

Application In Synthesis of [ 25309-64-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 25309-64-2 ]
Downstream synthetic route of [ 25309-64-2 ]

[ 25309-64-2 ] Synthesis Path-Upstream 1~21

1
[ 64-18-6 ]
[ 25309-64-2 ]
[ 4748-78-1 ]

Reference： [1] Chemistry - A European Journal, 2016, vol. 22, # 17, p. 5835 - 5838
[2] ChemCatChem, 2017, vol. 9, # 16, p. 3121 - 3124

2
[ 25309-64-2 ]
[ 937-30-4 ]

Reference： [1] Organic Letters, 2014, vol. 16, # 3, p. 948 - 951

3
[ 25309-64-2 ]
[ 5467-74-3 ]
[ 58743-79-6 ]

Reference： [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 26, p. 7530 - 7533[2] Angew. Chem., 2016, vol. 128, # 26, p. 7656 - 7659,4

4
[ 100-41-4 ]
[ 25309-64-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With iodine In acetonitrile at 40℃; for 1.5 h;	General procedure: Typical procedure. To a solution of 1,2-dimethylbenzene (0.106 g, 1 mmol) in acetonitrile (10 mL), iodine (1 mmol. 0.126 g) and polymer-supported periodic acid (0.6 g, 1.05 mmol) were added and the mixture was stirred for 1 hour at 40 °C. The reaction progress was monitored by thin layer chromatography (TLC) using a mixture of ethyl acetate and n-hexane (1:9 v/v) as solvent. After completion of the reaction, the mixture was cooled to room temperature and filtered. The excess of iodine was removed from the filtrate by drop wise addition of sodium bisulfite solution (1 M). The organic layers were separated, dried over magnesium sulfate, filtered, and the solvent was removed by evaporation. The residue was purified by column chromatography on silica gel using n-hexane and ethyl acetate. The related product was obtained with 95percent isolated yield, b.p.: 235 °C (lit. [18] b.p.: 234 °C).

Reference： [1] Bulletin of the Chemical Society of Ethiopia, 2014, vol. 28, # 2, p. 305 - 308
[2] Journal of applied chemistry of the USSR, 1984, vol. 57, # 1 pt 2, p. 121 - 123
[3] Journal fuer Praktische Chemie (Leipzig), 1902, vol. <2> 65, p. 568
[4] Journal of the Indian Chemical Society, 1936, vol. 13, p. 187
[5] Journal of the Indian Chemical Society, 1937, vol. 14, p. 157
[6] Justus Liebigs Annalen der Chemie, 1968, vol. 714, p. 91 - 111

5
[ 13329-40-3 ]
[ 25309-64-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With triethylsilane; indium(III) bromide In chloroform at 60℃; for 1 h; Inert atmosphere	General procedure: To a freshly distilled CHCl₃ solution (0.6 mL) in a screw-capped vial under N₂ atmosphere, InBr₃ (10.6 mg, 0.0300 mmol), aromatic ketone 4 (0.6 mmol) and Et₃SiH (383 μL, 2.40 mmol) was successively added. The resulting mixture was stirred at 60 °C (bath temperature) or room temperature, and monitored by TLC or GC analysis until consumption of the starting ketone. The reaction was quenched with H₂O. The aqueous layer was extracted with CH₂Cl₂ (5 mL .x. 3), the organic phases were dried over anhydrous Na₂SO₄, filtered, and evaporated under reduced pressure. The crude product was purified by a silica gel column chromatography (hexane/AcOEt = 19/1) to give the corresponding alkylbenzene 5. 1-Cyano-4-[1-(triethylsiloxy)ethyl]benzene (5k): 85percent yield; colorless oil; ¹H NMR (500 MHz, CDCl₃) δ 0.54-0.62 (m, 6H), 0.90-0.93 (m, 9H), 1.41 (d, 3H, J = 6 Hz), 4.90 (q, 1H, J = 6 Hz), 7.45 (d, 2H, J = 8 Hz), 7.61 (d, 2H, J = 8 Hz); ¹³C NMR (125 MHz, CDCl₃) δ 4.7, 6.7, 27.0, 69.9, 110.5, 119.0, 125.8, 132.0, 152.3; MS (ESI): m/z 284 (M⁺+Na); HRMS (ESI): Calcd for C₁₅H₂₃NNaOSi: 284.1447, Found: 284.1407.

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 24, p. 3133 - 3136
[2] Chemistry Letters, 1983, p. 909 - 910

6
[ 589-16-2 ]
[ 25309-64-2 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 11, p. 2175 - 2178

7
[ 96227-75-7 ]
[ 25309-64-2 ]

Reference： [1] Tetrahedron Letters, 2001, vol. 42, # 21, p. 3553 - 3554

8
[ 110-00-9 ]
[ 573-57-9 ]
[ 25309-64-2 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 11, p. 2175 - 2178

9
[ 98-69-1 ]
[ 25309-64-2 ]

Reference： [1] Tetrahedron Letters, 2010, vol. 51, # 45, p. 5950 - 5953

10
[ 2351-50-0 ]
[ 25309-64-2 ]

Reference： [1] Organometallics, 2010, vol. 29, # 9, p. 2098 - 2103

11
[ 100-41-4 ]
[ 25309-64-2 ]
[ 18282-40-1 ]

Reference： [1] Russian Journal of Organic Chemistry, 2000, vol. 36, # 5, p. 666 - 670
[2] Organic Process Research and Development, 2008, vol. 12, # 6, p. 1130 - 1136

12
[ 63139-21-9 ]
[ 25309-64-2 ]

Reference： [1] RSC Advances, 2015, vol. 5, # 103, p. 84910 - 84919

13
[ 96979-73-6 ]
[ 7553-56-2 ]
[ 25309-64-2 ]
[ 13121-86-3 ]

Reference： [1] Journal of the Chemical Society, [2] Journal of the Chemical Society, 1963, p. 681 - 689
[3] Poc. Chem. Soc., 1963, p. 51 - 51
[4] , Gmelin Handbook: Sn: Org.Verb.2, 1.1.2.11, page 339 - 345,

14
[ 100-63-0 ]
[ 25309-64-2 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1903, vol. 327, p. 286

15
[ 7803-49-8 ]
[ 25309-64-2 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1903, vol. 327, p. 286

16
[ 100-41-4 ]
[ 7664-93-9 ]
[ 7553-56-2 ]
[ 7697-37-2 ]
[ 64-19-7 ]
[ 25309-64-2 ]
[ 18282-40-1 ]

Reference： [1] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1957, p. 840,841, 846; engl. Ausg. S. 861, 862, 865

17
[ 25309-64-2 ]
[ 40307-11-7 ]

Reference： [1] Organic Letters, 2014, vol. 16, # 3, p. 948 - 951
[2] Angewandte Chemie, International Edition, 2015, vol. 54, # 19, p. 5697 - 5701[3] Angewandte Chemie, 2015, vol. 127, # 19, p. 5789 - 5793,5
[4] Organic and Biomolecular Chemistry, 2015, vol. 13, # 33, p. 8886 - 8892

18
[ 25309-64-2 ]
[ 7681-65-4 ]
[ 1066-54-2 ]
[ 40307-11-7 ]

Reference： [1] Patent: US2004/87789, 2004, A1,

19
[ 25309-64-2 ]
[ 5467-53-8 ]

Reference： [1] Patent: WO2008/112368, 2008, A2,

20
[ 25309-64-2 ]
[ 249647-25-4 ]

Reference： [1] Journal of the Indian Chemical Society, 1937, vol. 14, p. 157

21
[ 25309-64-2 ]
[ 53661-18-0 ]

Reference： [1] Chinese Journal of Chemistry, 2018, vol. 36, # 11, p. 1003 - 1006

[ 25309-64-2 ] Synthesis Path-Downstream 1~82

1
[ 100-41-4 ]
[ 25309-64-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With iodine; In acetonitrile; at 40℃; for 1.5h;	General procedure: Typical procedure. To a solution of 1,2-dimethylbenzene (0.106 g, 1 mmol) in acetonitrile (10 mL), iodine (1 mmol. 0.126 g) and polymer-supported periodic acid (0.6 g, 1.05 mmol) were added and the mixture was stirred for 1 hour at 40 C. The reaction progress was monitored by thin layer chromatography (TLC) using a mixture of ethyl acetate and n-hexane (1:9 v/v) as solvent. After completion of the reaction, the mixture was cooled to room temperature and filtered. The excess of iodine was removed from the filtrate by drop wise addition of sodium bisulfite solution (1 M). The organic layers were separated, dried over magnesium sulfate, filtered, and the solvent was removed by evaporation. The residue was purified by column chromatography on silica gel using n-hexane and ethyl acetate. The related product was obtained with 95% isolated yield, b.p.: 235 C (lit. [18] b.p.: 234 C).

Reference： [1]Bulletin of the Chemical Society of Ethiopia,2014,vol. 28,p. 305 - 308
[2]Journal of applied chemistry of the USSR,1984,vol. 57,p. 121 - 123
[3]Journal fur praktische Chemie (Leipzig 1954),1902,vol. <2> 65,p. 568
[4]Journal of the Indian Chemical Society,1936,vol. 13,p. 187
[5]Justus Liebigs Annalen der Chemie,1968,vol. 714,p. 91 - 111

2
[ 13329-40-3 ]
[ 25309-64-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With triethylsilane; indium(III) bromide; In chloroform; at 60℃; for 1h;Inert atmosphere;	General procedure: To a freshly distilled CHCl3 solution (0.6 mL) in a screw-capped vial under N2 atmosphere, InBr3 (10.6 mg, 0.0300 mmol), aromatic ketone 4 (0.6 mmol) and Et3SiH (383 muL, 2.40 mmol) was successively added. The resulting mixture was stirred at 60 C (bath temperature) or room temperature, and monitored by TLC or GC analysis until consumption of the starting ketone. The reaction was quenched with H2O. The aqueous layer was extracted with CH2Cl2 (5 mL × 3), the organic phases were dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The crude product was purified by a silica gel column chromatography (hexane/AcOEt = 19/1) to give the corresponding alkylbenzene 5. 1-Cyano-4-[1-(triethylsiloxy)ethyl]benzene (5k): 85% yield; colorless oil; 1H NMR (500 MHz, CDCl3) delta 0.54-0.62 (m, 6H), 0.90-0.93 (m, 9H), 1.41 (d, 3H, J = 6 Hz), 4.90 (q, 1H, J = 6 Hz), 7.45 (d, 2H, J = 8 Hz), 7.61 (d, 2H, J = 8 Hz); 13C NMR (125 MHz, CDCl3) delta 4.7, 6.7, 27.0, 69.9, 110.5, 119.0, 125.8, 132.0, 152.3; MS (ESI): m/z 284 (M++Na); HRMS (ESI): Calcd for C15H23NNaOSi: 284.1447, Found: 284.1407.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 3133 - 3136
[2]Chemistry Letters,1983,p. 909 - 910

3
[ 25309-64-2 ]
[ 536-74-3 ]
[ 29778-20-9 ]

Yield	Reaction Conditions	Operation in experiment
93.3%	With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 12h;Schlenk technique;	General procedure: A 100 mL Schlenk flask was charged with 2-bromopyridine (1.1 mmol), phenylacetylene (0.92 mmol), Cs2CO3 (1.84 mmol), 1-Pd (0.003 mmol based on Pd), DMF (6 mL) and the reaction mixture was stirred at 100 C under air atmosphere for 12 h. The mixture was cooled to the room temperature; the solid was removed by filtration and washed twice with DMF (3 mL). The filtrate was collected, dried and the residue was extracted with ethyl acetate (3 x 3 mL) followed by purification with silica gel chromatography (petroleum ether) to give a corresponding product.
68%	With 1,4-diaza-bicyclo[2.2.2]octane; manganese(III) triacetate dihydrate; at 70℃;Green chemistry;	General procedure: In a 25 mL reaction tube, Mn(OAc)3.2H2O(10 mol%), DABCO (2.5 equiv.) and a stirring bar were added. Then iodobenzene(1 mmol), phenyl acetylene (1 mmol) and PEG-400 were injected by syringe. The reaction tube was closed and transferred to a 70 C oil bath for 19-24 hours. After the reaction completed, cool down the reaction mixture to room temperature. Water (2 mL) was added and the reaction mixture was extracted with ethyl acetate and then concentrated and purified by column chromatography.

Reference： [1]Catalysis science and technology,2016,vol. 6,p. 2050 - 2054
[2]Journal of Catalysis,2016,vol. 344,p. 445 - 454
[3]RSC Advances,2016,vol. 6,p. 109296 - 109300
[4]Tetrahedron Letters,2016,vol. 57,p. 1706 - 1710
[5]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 308 - 311
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 355 - 359
[6]Synlett,2005,p. 487 - 488
[7]Chemical Science,2018,vol. 9,p. 4650 - 4661

4
[ 25309-64-2 ]
[ 74-86-2 ]
[ 79135-69-6 ]

Yield	Reaction Conditions	Operation in experiment
44%	With copper(l) iodide; diethylamine; triphenylphosphine; palladium dichloride at 54 - 55℃; for 8h;

Reference： [1]Merkushev, E. B.; Skorokhodova, T. S. [Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 308 - 311][Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 2, p. 355 - 359]

5
[ 153-78-6 ]
[ 25309-64-2 ]
Bis-(4-ethyl-phenyl)-(9H-fluoren-2-yl)-amine [ No CAS ]

Reference： [1]Journal of Physical Chemistry A,1997,vol. 101,p. 8157 - 8165

6
[ 25309-64-2 ]
[ 1066-54-2 ]
(2-(4-ethylphenyl)ethynyl)trimethylsilane [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 7091 - 7094
[2]Organic Letters,2014,vol. 16,p. 948 - 951
[3]Angewandte Chemie - International Edition,2015,vol. 54,p. 5697 - 5701
Angew. Chem.,2015,vol. 127,p. 5789 - 5793,5
Angewandte Chemie,2015,vol. 127,p. 5789 - 5793,5
[4]Organic Letters,2009,vol. 11,p. 3210 - 3213
[5]Canadian Journal of Chemistry,2008,vol. 86,p. 410 - 415
[6]Organic and Biomolecular Chemistry,2015,vol. 13,p. 8886 - 8892

7
[ 141-32-2 ]
[ 25309-64-2 ]
4-ethyl-trans-cinnamic acid n-butyl ester [ No CAS ]

Reference： [1]Organic Letters,2003,vol. 5,p. 3209 - 3212

8
[ 292638-84-7 ]
[ 25309-64-2 ]
[ 24942-80-1 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 225 - 228

9
[ 25309-64-2 ]
[ 107-19-7 ]
[ 918625-92-0 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; triphenylphosphine;tris(dibenzylideneacetone)dipalladium(0) chloroform complex; copper(l) iodide; In tetrahydrofuran; at 20℃; for 12h;	(39-1) Synthesis of 3-(4-ethylphenyl)-2-propyne-l-ol (compound 39-1) [Show Image] A mixture of 4-ethyliodobenzene (5.00 g), copper(I) iodide (82.1 mg), triphenylphosphine (283 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (446 mg), propargyl alcohol (1.40 ml), diisopropylethylamine (15.0 ml) and tetrahydrofuran (100 ml) was stirred at room temperature for 12 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=98:2 - 80:20) to give the object product (2.10 g) as a brown oil. 1H-NMR(CDCl3) delta (ppm): 1.23(3H, t, J=7.6Hz), 1.65(1H, t, J=6.0Hz), 2.64(2H, q, J=7.6Hz), 4.49(2H, d, J=5.9Hz), 7.15(2H, d, J=7.6Hz), 7.36(2H, d, J=7.6Hz).

Reference： [1]Advanced Synthesis and Catalysis,2006,vol. 348,p. 545 - 550
[2]Patent: EP2168944,2010,A1 .Location in patent: Page/Page column 90
[3]Chemistry - A European Journal,2014,vol. 20,p. 5910 - 5913
[4]Angewandte Chemie - International Edition,2018,vol. 57,p. 8734 - 8738
Angew. Chem.,2018,vol. 130,p. 8870 - 8874,5
[5]Organic Letters,2019,vol. 21,p. 8308 - 8311
[6]Organic and Biomolecular Chemistry,2019,vol. 17,p. 8737 - 8744

10
[ 25309-64-2 ]
[ 249647-25-4 ]

Reference： [1]Journal of the Indian Chemical Society,1937,vol. 14,p. 157

11
[ 624-38-4 ]
[ 25309-64-2 ]
[ 17078-76-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: para-diiodobenzene With tetramethylurea; zinc at 130℃; for 72h; Stage #2: 4-ethyl-1-iodobenzene With tri-tert-butyl phosphine; tetramethylurea In tetrahydrofuran at 20℃; for 1h; Stage #3: With iodine In tetrahydrofuran at 20℃; for 3h; Further stages.;

Reference： [1]Kawamoto, Takahiro; Ejiri, Shogo; Kobayashi, Kana; Odo, Shunsuke; Nishihara, Yasushi; Takagi, Kentaro [Journal of Organic Chemistry, 2008, vol. 73, # 4, p. 1601 - 1604]

12
[ 14660-52-7 ]
[ 25309-64-2 ]
C₁₅H₂₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A 250 mL 3-neck round bottom flask equipped with a thermometer and a magnetic stirring bar was charged with 4.01 g (61.3 mmol) of zinc dust and 35 mL of dimethylformamide (DMF) under a nitrogen atmosphere. The slurry was treated with 0.56 g (2.2 mmol) of iodine. The red disappeared in 90 seconds. The reaction mixture was treated with 6.00 mL (8.18 g, 42.0 mmol) of ethyl 4-bromopentanoate and heated to 800C for 4 hour. The reaction mixture was cooled to 300C and treated with 4.98 g (21.5 mmol) of 4-iodoethylbenzene and 0.48 g (0.9 mmol) of dichlorobis(triphenylphosphine)nickel(II). The reaction mixture was heated to 45C for 80 hours. The cooled reaction mixture was treated with aqueous 4% hydrochloric acid to quench the excess zinc. The mixture was extracted with methyl t-butyl ether (MTBE) (1 X 60 mL). The organic phase was washed with brine (1 X 30 mL), dried over sodium sulfate and concentrated. The crude ethyl 4-(4-ethylphenyl)pentanoate was taken up in ethanol, treated with 20 mL of 2N aqueous sodium hydroxide, and heated to reflux. After 4 hours the reaction mixture was cooled to 25C and washed with MTBE (2 X 30 mL). The aqueous phase was acidified with aqueous 4% hydrochloric acid. A solid was isolated by filtration to give 1.99 g of 4-(4-ethylphenyl)pentanoic acid. IH NMR (d6- DMSO): delta 11.9, bs, IH (COOH); delta 6.98, d, 2H, (arylH's); delta 6.95, d, 2H (arylH's); delta 2.42, <n="41"/>m, 4H, (CH2's alpha to aryl); delta 2.09, t, 2H (CH2 alpha to COOH); delta 1.4, m, 2H (CH2's beta to aryl aanndd CCOOOOHH));; deltadelta 11..0033,, tt,, 33HH ((CCHH33)).. 1133CC NNMMRR ((dd66--EDMS0): 174.38, 140.90, 139.11, 128.15,127.57, 34.39, 33.49, 30.45, 27.73, 24.09, 15.66.

Reference： [1]Patent: WO2008/112368,2008,A2 .Location in patent: Page/Page column 39-40

13
[ 2969-81-5 ]
[ 25309-64-2 ]
[ 412321-18-7 ]

Yield	Reaction Conditions	Operation in experiment
		A 250 mL 3 -neck round bottom flask equipped with a thermometer and a magnetic stirring bar was charged with 4.01 g (61.3 mmol) of zinc dust and 35 mL of dimethylformamide (DMF) under a nitrogen atmosphere. The slurry was treated with 0.56 g (2.2 mmol) of iodine. The red disappeared in 90 seconds. The reaction mixture was treated with 6.00 mL (8.18 g, 42.0 mmol) of ethyl 4-bromobutyrate and heated to 800C for 4 hour. The reaction mixture was cooled to 300C and treated with 4.98 g (21.5 mmol) of 4-iodoethylbenzene and 0.48 g (0.9 mmol) of dichlorobis(triphenylphosphine)nickel(II). The reaction mixture was heated to 45C for 80 hours. The cooled reaction mixture was treated with aqueous 4% hydrochloric acid to quench the excess zinc. The mixture was extracted with methyl t-butyl ether (MTBE) (1 X 60 mL). The organic phase was washed with brine (1 X 30 mL), dried over sodium sulfate and concentrated. The crude ethyl 4-(4-ethylphenyl)butyrate was taken up in ethanol, treated with 20 mL of 2N aqueous sodium hydroxide, and heated to reflux. After 4 hours the reaction mixture was cooled to 25C and washed with MTBE (2 X 30 mL). The aqueous phase was acidified with aqueous 4% hydrochloric acid. A solid was isolated by filtration to give 1.99 g of 4-(4-ethylphenyl)butanoic acid. IH NMR (d6- DMSO): delta 11.9, bs, IH (COOH); delta 6.98, d, 2H, (arylH's); delta 6.95, d, 2H (arylH's); delta 2.41, m, 4H, (CH2's alpha to aryl); delta 2.07, t, 2H (CH2 alpha to COOH); delta 1.64, m, 2H (CH2 beta to both aryl and COOH); delta 1.03, t, 3H (CH3). 13C NMR (d6-DMSO): 174.23, 141.08, 138.67, 128.20, 127.65, 33.97, 33.03, 27.73, 26.35, 15.65.

Reference： [1]Patent: WO2008/112368,2008,A2 .Location in patent: Page/Page column 38

14
[ 3054-95-3 ]
[ 25309-64-2 ]
[ 119200-32-7 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 3363 - 3366
[2]Angewandte Chemie - International Edition,2013,vol. 52,p. 12619 - 12623
Angew. Chem.,2013,p. 12851 - 12855,5

15
[ 201230-82-2 ]
[ 25309-64-2 ]
[ 536-74-3 ]
[ 742699-27-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With triethylamine; In water; at 130℃; under 22502.3 Torr; for 6h;Autoclave;	In a typical experiment, known quantities of iodobenzene (1.0 mmol), phenylacetylene (1.2 mmol), P(DVB-IL)-Pd (20 mg, Pd 0.5 mol %), Et3N (0.4 mL, 2.4 mmol), and distilled water (5.0 mL) were charged into the reactor. The autoclave was closed, purged three times with CO, pressurized to 3.0 MPa with CO, and then stirred at 130 C for 6 h. After cooling down to room temperature, the reaction mixture was analyzed by GC-MS and then worked up by removing water under vacuum and the residue was purified by chromatography on silica gel (eluting solvent hexane:ethyl acetate).

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1587 - 1591
[2]RSC Advances,2017,vol. 7,p. 31850 - 31857
[3]Organic Letters,2008,vol. 10,p. 3933 - 3936

16
[ 110-91-8 ]
[ 201230-82-2 ]
[ 25309-64-2 ]
[ 1127405-04-2 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 1321 - 1324

17
[ 288-32-4 ]
[ 25309-64-2 ]
[ 59066-78-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With Pd(tris[2-(diphenylphosphino)ethyl]phosphine tetrasulfide)(dibenzylideneacetone); caesium carbonate; In isopropyl alcohol; at 80℃; for 2.5h;	General procedure: To a stirred solution of aryl halide (1.2mmol) and [Pd(pp3S4)(dba)] (1mol %) in isopropanol (2.5ml) was added nitrogen/oxygen nucleophile (1mmol) followed by Cs2CO3 (2mol %) in the atmosphere of air. The mixture was heated to 80C and the progress of the reaction was monitored by TLC. After completion, the solvent was evaporated through rotavapour and the crude mixture was washed with dichloromethane-H2O and the organic phase was separated and dried over Na2SO4. The dichloromethane was evaporated followed by flash column purification on silica gel of the crude to obtain the pure products. The products were characterized using 1H, 13C NMR spectroscopy and GC-MS spectroscopy. The characterization data were in good agreement with those described in the literature.

Reference： [1]Journal of Organometallic Chemistry,2015,vol. 781,p. 23 - 34
[2]Journal of Organic Chemistry,2009,vol. 74,p. 7514 - 7517
[3]Advanced Synthesis and Catalysis,2010,vol. 352,p. 3241 - 3245

18
[ 25309-64-2 ]
[ 107-18-6 ]
[ 119200-32-7 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 415 - 417

19
[ 25309-64-2 ]
[ 98-80-6 ]
[ 5707-44-8 ]

Reference： [1]Chinese Journal of Chemistry,2011,vol. 29,p. 525 - 530
[2]Advanced synthesis and catalysis,2012,vol. 354,p. 2911 - 2915,5
[3]ChemCatChem,2013,vol. 5,p. 142 - 145
[4]Chemical Communications,2010,vol. 46,p. 6524 - 6526
[5]Applied Organometallic Chemistry,2013,vol. 27,p. 519 - 522

20
[ 25309-64-2 ]
[ 25015-63-8 ]
[ 1075719-87-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With magnesium; triethylamine; In tetrahydrofuran; for 15h;Reflux;	Example 1Preparation of pinacol ester of 4-ethylphenylboronic acid In a 2 necks Schlenk type flask, provided with a magnetic stirring bar and topped by a coolant, 4-ethylbenzene iodide (0.232 g, 1 mmol), pinacolborane (0.128 g, 1 mmol) and triethylamine (59 mg, 1 mmol) are added to 10 ml of a distilled THF solution containing magnesium turnings (24 mg, 1 mmol). The reactive mixture is stirred for approximately 15 hours at THF reflux.At the end of the reaction, the crude reaction product is hydrolyzed by 20 ml of neutral water and extracted by diethyl ether (3×40 ml). The joined organic phases are washed by 2×50 ml of neutral water then dried on MgSO4. After solvent evaporation, the obtained yield is of 96% with a total conversion of the starting iodide (yield/conversion of 96%). The resulting boronic ester is analyzed by GC, NMR 1H and 13C and GC/MS.Characterizations:NMR 1H, 7.74 (2H, D, 3 Hz); 7.22 (2H, D, 3 Hz); 2.66 (2H, Q, 3 Hz); 1.34 (12H, s); 1.24 (3H, T, 3 Hz).NMR 13C, 146.68; 133.87; 127.23; 126.31; 82.58; 28.08; 23.82; 14.42.Mass spectrometry: 232-231 (M+, 6-2%); 217-216 (8-2%); 147 (19%); 146-145 (71-15%); 134 (17%); 133 (100%); 132-131 (63-21%); 118 (18%); 117 (51%); 116-115 (17-4%); 105 (18%); 104 (10%); 91 (11%); 85 (14%); 77-76 (9-2%).Ultimate Analyses:calculated %: C: 72.44%; H: 9.12%; B: 4.66%.obtained %: C: 70.22%; H: 9.25%; b: 4.39%.

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 11825 - 11827
[2]Patent: US2011/282090,2011,A1 .Location in patent: Page/Page column 5-6

21
[ 25309-64-2 ]
[ 536-74-3 ]
[ 571168-92-8 ]
[ 1092976-38-9 ]

Yield	Reaction Conditions	Operation in experiment
44.1%		13.20 g (31.64 mmol) of 1-benzyl-4-(benzyloxy)-3-iodopyridin-2(1H)-one are, together with 26.4 ml of triethylamine, initially charged in 224 ml of acetonitrile. 1.11 g (1.58 mmol) of bis(triphenylphosphine)palladium(II) chloride, 301 mg (1.58 mmol) of copper(I) iodide and 4.20 g (41.13 mmol) of ethynylbenzene are added, and the mixture is, under argon and with stirring, heated at 60 C. for 22 h. The mixture is then allowed to cool to room temperature, 11.01 g (47.45 mmol) of 4-ethyliodobenzene are added and the mixture is once more, under argon and with stirring, heated at 60 C. for 24 h. The mixture is then concentrated and filtered through silica gel (mobile phase: cyclohexane/ethyl acetate 1:1, then dichloromethane/methanol 95:5). The product-containing fractions are combined and concentrated. The product obtained in this manner is once more purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol 100:3). The product-containing fractions are once more combined and concentrated. The residue is dissolved in warm ethyl acetate, a little activated carbon is added, the mixture is briefly heated to the boil and the activated carbon is filtered off again. After cooling to room temperature, the precipitated crystals are filtered off with suction, and more crystals are obtained from the mother liquor. In this manner, a total of 6.00 g (44.1% of theory) of the target compound are obtained.LC-MS (method 1): Rt=2.86 min; m/z=406 (M+H)+ 1H-NMR (400 MHz, CDCl3): delta=7.85 (d, 1H), 7.49-7.23 (m, 11H), 7.22 (d, 2H), 6.05 (d, 1H), 5.45 (s, 2H), 2.69-2.61 (q, 2H), 1.26-1.21 (t, 3H).

Reference： [1]Patent: US2010/261736,2010,A1 .Location in patent: Page/Page column 32

22
[ 25309-64-2 ]
[ 51-35-4 ]
[ 383137-78-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With copper(II) ferrite; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 20h;Inert atmosphere;	General procedure: To astirred solution of: Aryl iodide (1.0 mmol), trans-4-Hydroxy-L-proline (1.5 mmol), nano CuFe2O4 (0.01 mmol), base (2 equiv), solvent (3.0 mL), 20h, 100 oC. The progress of the reaction was monitored by TLC. After the reaction was complete CuFe2O4 nano were placed on the bottom of the flask by a neodymium magnet, and the supernatant solution was removed. The crude residue was extracted with ethyl acetate (3 x 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4.The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography to give the corresponding N-substituted pyrrole in excellent yields. The identity and purity of the product were confirmed by 1H,13C NMR, and mass spectra.
89%	With copper(l) iodide; caesium carbonate; In dimethyl sulfoxide; at 110℃; for 24h;	General procedure: to a stirred solution of iodo benzene (1.0 mmol) and trans-4-hydroxy-L-proline (2.0 equiv) in dry DMSO (3.0 mL) at rt was added CuI (20 mol %) followed by Cs2CO3 (2.5 equiv) and heated at 110 C for 24 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (20 mL) was added. The combined organic extracts were dried with anhydrous Na2SO4. The solvent and volatiles were completely removed under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 9:1) to afford the corresponding coupling product.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 2596 - 2599
[2]Tetrahedron Letters,2011,vol. 52,p. 777 - 780

23
[ 591-50-4 ]
[ 25309-64-2 ]
[ 139-66-2 ]
[ 19164-74-0 ]
[ 132260-92-5 ]

Yield	Reaction Conditions	Operation in experiment
55%; 31%; 48%	With caesium carbonate; thiourea; copper(II) oxide; In dimethyl sulfoxide; at 20 - 110℃;Inert atmosphere;	General procedure: To a stirred solution of aryl halides (2.0 mmol) and thiourea (1.2 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 110 C for 15 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (20 mL) was added. The combined organic extracts were dried with anhydrous Na2SO4. The solvent and volatiles were completely removed under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 9:1) to afford the corresponding coupling product in excellent yields.Recycling of the catalyst:after the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (2.0 mL) was added and CuO was removed by centrifugation. After each cycle, the catalyst was recovered by simple centrifugation, washing with deionized water and ethyl acetate and then drying in vacuo. The recovered nano CuO was used directly in the next cycle.Data of representative examples:Dip-tolylsulfane (Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Bis(4-ethylphenyl)sulfane (Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Bis(3-nitrophenyl)sulfane (Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.4,4'-Thiodianiline (Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Dithiophen-3-ylsulfane (Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Dipyrimidin-5-ylsulfane (Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; found: C, 50.45; H, 3.13; N, 29.41; S, 16.81.Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; f...

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2679 - 2682

24
[ 25309-64-2 ]
[ 132260-92-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With caesium carbonate; thiourea; copper(II) oxide; In dimethyl sulfoxide; at 20 - 110℃;Inert atmosphere;	General procedure: To a stirred solution of aryl halides (2.0 mmol) and thiourea (1.2 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 110 C for 15 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (20 mL) was added. The combined organic extracts were dried with anhydrous Na2SO4. The solvent and volatiles were completely removed under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 9:1) to afford the corresponding coupling product in excellent yields.Recycling of the catalyst:after the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (2.0 mL) was added and CuO was removed by centrifugation. After each cycle, the catalyst was recovered by simple centrifugation, washing with deionized water and ethyl acetate and then drying in vacuo. The recovered nano CuO was used directly in the next cycle.Data of representative examples:Dip-tolylsulfane (Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Bis(4-ethylphenyl)sulfane (Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Bis(3-nitrophenyl)sulfane (Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.4,4'-Thiodianiline (Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Dithiophen-3-ylsulfane (Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Dipyrimidin-5-ylsulfane (Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; found: C, 50.45; H, 3.13; N, 29.41; S, 16.81.Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; f...

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 2297 - 2307
[2]Tetrahedron Letters,2011,vol. 52,p. 2679 - 2682
[3]Beilstein Journal of Organic Chemistry,2011,vol. 7,p. 886 - 891

25
[ 25309-64-2 ]
bis(4-ethylphenyl)selane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With copper(l) iodide; (1R,2R)-1,2-diaminocyclohexane; water; potassium selenocyanate; caesium carbonate; at 100℃; for 24h;Air atmosphere;	General procedure: Aryl halide (1.0 mmol), CuI (10 mol %), L4 (10 mol %), Cs2CO3 (2.0 equiv) and potassium selenocyanate (1.2 mmol) were charged in a 10 ml round bottom flask with a condenser under air, followed by the addition of water (3.0 mL). The reaction mixture was heated in an oil bath at 100 C and stirred at this temperature for 24 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was allowed to cool, and treated with ethyl acetate. The combined organic extracts were dried with anhydrous Na2SO4. The solvent and volatiles were completely removed under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 9:1) to afford the corresponding coupling product in excellent yields. All the products were characterized by 1H and 13C NMR, MS and compared with the literature values.

Reference： [1]Synlett,2011,p. 1268 - 1272
[2]Tetrahedron Letters,2011,vol. 52,p. 3978 - 3981

26
[ 1146968-99-1 ]
[ 25309-64-2 ]
[ 1146969-10-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	With [ruthenium(II)(eta6-1-methyl-4-isopropyl-benzene)(chloride)(mu-chloride)]2; potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 120℃; for 18h;	General procedure: To the mixture of [RuCl2(p-cymene)]2 (0.05 equiv), K2CO3 (2 equiv), 1a (1 equiv), 2a (1.5 equiv) and 3 mL NMP were added successively. The mixture was stirred at 120 C for 18 h. The solution was extracted with ethyl acetate (3 x 15 mL), and the combined extract was dried with anhydrous MgSO4. Solvent was removed, and the residue was separated by column chromatography to give the pure sample 3a.

Reference： [1]Synlett,2011,p. 1472 - 1476
[2]Journal of Organometallic Chemistry,2011,vol. 696,p. 3086 - 3090

27
[ 25309-64-2 ]
[ 1335105-21-9 ]
[ 1335105-26-4 ]

Yield	Reaction Conditions	Operation in experiment
79%	With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; potassium phosphate; copper(l) iodide; In 1,4-dioxane; at 110℃;Inert atmosphere;	General procedure: After standard evacuation and back-fill cycles with argon, a Schlenk tube fitted with a magnetic stirrer bar was charged with pyrazole derivative (1.29 mmol), aryl iodide (1.1 eq), K3PO4 (2 eq) and copper iodide (0.1 eq). N,N'-dimethyl-cyclohexane-1,2-diamine (0.2 eq) and anhydrous dioxane (3 mL) were then added under a stream of argon by syringe at room temperature. The sealed tube is stirred at 110 C for 24-48 h. A 28% solution of ammonia and water are added at room temperature to the reaction mixture. The resulting aqueous layer is extracted with DCM. The combined organic layers are dried on MgSO4, filtered and evaporated under reduced pressure. The residue is triturated in an appropriate solvent or purified on silica gel.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3867 - 3876

28
[ 934-37-2 ]
[ 25309-64-2 ]
[ 1366591-44-7 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 1688 - 1691

29
[ 25309-64-2 ]
[ 1398501-45-5 ]
[ 1377891-59-2 ]

Yield	Reaction Conditions	Operation in experiment
90%		To a cold (-78 C) solution of 32 (440 mg, 0.639 mmol) in CH2Cl2 (30 mL) was added diisobutylalminiumhydride (1.0 M in hexane; 0.96 mL, 0.96 mmol) and the mixture was stirred at 0 C for 3 h. To the reaction mixture was added saturated aqueous ammonium chloride solution then the resulting insoluble portion was filtered through celite. The filtrate was extracted with CHCl3 and the organic layer was dried over MgSO4, filtered and evaporated in vacuo. The resulting residue was purified by column chromatography on silica gel (EtOAc-hexane) to give aldehyde (250 mg, 62%) as a colorless oil. To a cold (-30 C) solution of <strong>[25309-64-2]1-ethyl-4-iodobenzene</strong> (0.29 mL, 1.98 mmol) in THF (10 mL) was added iPrMgCl (2.0 M in THF; 0.95 mL, 1.90 mmol) and the mixture was stirred at -30 C for 2 h. To the reaction mixture was added a solution of aldehyde obtained above (250 mg, 0.40 mmol) in THF (10 mL) and the mixture was stirred at rt for 2.5 h. To the reaction mixture was added saturated aqueous ammonium chloride solution then extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The resulting residue was purified by column chromatography on silica gel (EtOAc-hexane) to give the title compound (33) (274 mg, 90%) as a colorless oil.1H NMR (CDCl3) delta: 1.15 (3H, t, J = 6.8 Hz), 2.56 (2H, q, J = 6.8 Hz), 3.62-4.01 (7H, m), 4.37-4.68 (5H, m), 4.84-4.97 (3H, m), 5.72 (1H, br s), 6.76-6.85 (2H, m), 7.02-7.36 (24H, m), 7.57 (1H, t, J = 8.0 Hz). MS (FAB) m/z: 736 (M++H), calcd for C48H49NO6: 735.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 3263 - 3279

30
[ 496-15-1 ]
[ 25309-64-2 ]
[ 1380481-43-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With caesium carbonate; copper(II) oxide; In dimethyl sulfoxide; at 80℃; for 8h;	General procedure: To a stirred solution of aryl halides (1.0 mmol) and indoline/indoline carboxylic acid (1.0 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 80 C for 8 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was cooled to room temperature and catalyst was filtered, the crude residue was extracted with ethyl acetate (3 × 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (7:3) as eluent to give the corresponding N-substituted indoles in excellent yields. The identity and purity of the product were confirmed by 1H, 13C NMR, and mass spectra.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 3061 - 3065

31
[ 32692-19-6 ]
[ 25309-64-2 ]
[ 1380481-46-8 ]

Yield	Reaction Conditions	Operation in experiment
77%	With caesium carbonate; copper(II) oxide; In dimethyl sulfoxide; at 80℃; for 8h;	General procedure: To a stirred solution of aryl halides (1.0 mmol) and indoline/indoline carboxylic acid (1.0 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 80 C for 8 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was cooled to room temperature and catalyst was filtered, the crude residue was extracted with ethyl acetate (3 × 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (7:3) as eluent to give the corresponding N-substituted indoles in excellent yields. The identity and purity of the product were confirmed by 1H, 13C NMR, and mass spectra.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 3061 - 3065

32
[ 25309-64-2 ]
[ 16851-56-2 ]
[ 1380481-43-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With caesium carbonate; copper(II) oxide; In dimethyl sulfoxide; at 80℃; for 8h;	General procedure: To a stirred solution of aryl halides (1.0 mmol) and indoline/indoline carboxylic acid (1.0 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 80 C for 8 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was cooled to room temperature and catalyst was filtered, the crude residue was extracted with ethyl acetate (3 × 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (7:3) as eluent to give the corresponding N-substituted indoles in excellent yields. The identity and purity of the product were confirmed by 1H, 13C NMR, and mass spectra.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 3061 - 3065

33
[ 25309-64-2 ]
[ 98-80-6 ]
[ 92-52-4 ]
[ 5707-44-8 ]

Yield	Reaction Conditions	Operation in experiment
10%; 88%	With trans-1,2-Diaminocyclohexane; potassium tert-butylate; silver(I) acetate; In dimethyl sulfoxide; at 150℃; for 7.5h;Inert atmosphere;	General procedure: To a stirred solution of boronic acid (1.2 mmol) and AgOAc (16 mg, 10 mol percent) in dry DMSO (3 ml) was added aryl iodides/bromides (1 mmol) followed by trans-1,2-diaminocyclohexane (0.006 ml, 10 mol percent) and KOtBu (224 mg, 2 equiv) under a nitrogen atmosphere. The mixture was heated to 150 C and the progress was monitored by TLC. After completion, the reaction mixture was washed with EtOAc-H2O and the organic phase was separated and dried over Na2SO4. The EtOAc was evaporated followed by flash column purification on silica gel to obtain the pure products.#10;

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 7023 - 7027

34
[ 1131-16-4 ]
[ 201230-82-2 ]
[ 25309-64-2 ]
(2-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl)(4-ethylphenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With benz<b>oxazole; (η4-1,5-cyclooctadiene)dichlororuthenium(II); potassium acetate; sodium hydrogencarbonate In water at 120℃; for 20h; Autoclave; Inert atmosphere;

Reference： [1]Tlili, Anis; Schranck, Johannes; Pospech, Jola; Neumann, Helfried; Beller, Matthias [Angewandte Chemie - International Edition, 2013, vol. 52, # 24, p. 6293 - 6297][Angew. Chem., 2013, vol. 125, # 24, p. 6413 - 6417,5]

35
[ 25309-64-2 ]
[ 74299-48-2 ]
(3aS,6aR,9aR,9bS,E)-3-(4-ethylbenzylidene)-6,9-dimethylenedecahydroazuleno[4,5-b]furan-2(9bH)-one [ No CAS ]
(3aS,6aR,9aR,9bS,Z)-3-(4-ethylbenzylidene)-6,9-dimethylenedecahydroazuleno[4,5-b]furan-2(9bH)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%; 6%	With palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 80℃; for 20.0h;	General procedure: A mixture of compound 2 (500 mg, 1.38 mmol), triethylamine (0.6 mL, 4.14 mmol), and 1-chloro-4-iodobenzene (1.55 mmol) in DMF (3.45 mL) was treated with palladium(II) acetate (15.5 mg, 0.04 mmol) and then heated at 80 ºC under air. After 20 h, the resulting solution was allowed to cool to room temperature, water (7 mL) was added, and the resultant mixture was extracted with ether (7 mL × 5). The organics was dried over Na2SO4 and concentrated under reduced pressure to give a crude residue, which was purified by silica gel column chromatography to afford the product.#10;

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6087 - 6092

36
[ 25309-64-2 ]
(3aS,9R,9aS,9bS)-6,9-dimethyl-3-methylene-9-((triethylsilyl)oxy)-3,3a,4,5,7,8,9,9a-octahydroazuleno[4,5-b]furan-2(9bH)-one [ No CAS ]
(3aS,9R,9aS,9bS,E)-3-(4-ethylbenzylidene)-6,9-dimethyl-9-((triethylsilyl)oxy)-3,3a,4,5,7,8,9,9a-octahydroazuleno[4,5-b]furan-2(9bH)-one [ No CAS ]
(3aS,9R,9aS,9bS,Z)-3-(4-ethylbenzylidene)-6,9-dimethyl-9-((triethylsilyl)oxy)-3,3a,4,5,7,8,9,9a-octahydroazuleno[4,5-b]furan-2(9bH)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%; 12%	With palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 80℃; for 20h;	General procedure: A mixture of compound 2 (500 mg, 1.38 mmol), triethylamine (0.6 mL, 4.14 mmol), and 1-chloro-4-iodobenzene (1.55 mmol) in DMF (3.45 mL) was treated with palladium(II) acetate (15.5 mg, 0.04 mmol) and then heated at 80 ºC under air. After 20 h, the resulting solution was allowed to cool to room temperature, water (7 mL) was added, and the resultant mixture was extracted with ether (7 mL × 5). The organics was dried over Na2SO4 and concentrated under reduced pressure to give a crude residue, which was purified by silica gel column chromatography to afford the product.
78%; 12%	With palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 80℃; for 8h;	Compound 2 (120mg, 0.37mmol) was dissolved in DMF (0.8mL, 0.47mol / L), was added Et3N (0.14mL, 1.11mmol), 1- ethyl-4-iodo-benzene (97.2mg, 0.42mmol), stir, add Pd (OAc)2(3.71mg, 0.017mmol), gradually warmed to 80 , heated to reflux for 8h, the reaction was monitored by TLC, After completion of the reaction, the reaction solution was cooled to room temperature.Addition of distilled water (20mL), and extracted with anhydrous diethyl ether (20mL × 5), and the organic layer was washed with Na2SO4Drying, rotary evaporation, purified by silica gel column to give product 3E (78% yield) and 4E (yield 12%).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6087 - 6092
[2]Patent: CN104211669,2018,B .Location in patent: Paragraph 0073 - 0076

37
[ 25309-64-2 ]
[ 71-43-2 ]
[ 5707-44-8 ]

Reference： [1]Chemistry - An Asian Journal,2014,vol. 9,p. 439 - 442
[2]Angewandte Chemie - International Edition,2016,vol. 55,p. 3124 - 3128
Angew. Chem.,2016,vol. 128,p. 3176 - 3180,5

38
[ 25309-64-2 ]
[ 393827-07-1 ]
[ 1565872-70-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With tetrabutylammomium bromide; palladium diacetate; triethylamine; 1,3-di-tert-butyl-1H-imidazol-3-ium chloride; In ethanol; water; at 80℃; for 5h;	General procedure: Heck coupling reactions were carried out using aryl iodides (3a-j) (1 mmol), 2-Vinyl-N-Boc-piperidine (2) (1.2 mmol), and Et3N as base (2 mmol) dissolved in 10 ml of aq.ethanol (water/ethanol = 9:1). An appropriate amount of NHC precursor (i) (0.1 mmol), Pd(OAc)2 (0.05 mmol), and TBAB (0.025 mmol) were added to this mixture. The reaction mixture was heated to 80 C for 5 hrs. The coupled product was extracted with DCM (2 x 20 ml). The combined organic layers were dried (anhydrous Na2SO4) and evaporated under reduced pressure to afford a crude product which was subjected to column chromatography to afford pure E-Olefins (4a-j).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1180 - 1183

39
[ 25309-64-2 ]
[ 274-79-3 ]
[ 1606131-42-3 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 1589 - 1593
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 1589 - 1593

40
[ 25309-64-2 ]
[ 40307-11-7 ]
[ 79135-69-6 ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 4h; Inert atmosphere;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In water; benzene at 80℃;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine In tetrahydrofuran; triethylamine at 20℃; Inert atmosphere; Schlenk technique;

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In water; benzene at 80℃;

Reference： [1]Yu, Yue; Huang, Liangbin; Wu, Wanqing; Jiang, Huanfeng [Organic Letters, 2014, vol. 16, # 8, p. 2146 - 2149]
[2]Li, Tongyu; Liu, Chang; Wu, Shaonan; Chen, Chen C.; Zhu, Bolin [Organic and Biomolecular Chemistry, 2019, vol. 17, # 33, p. 7679 - 7683]
[3]Yang, Qi-Liang; Xing, Yi-Kang; Wang, Xiang-Yang; Ma, Hong-Xing; Weng, Xin-Jun; Yang, Xiang; Guo, Hai-Ming; Mei, Tian-Sheng [Journal of the American Chemical Society, 2019, vol. 141, # 48, p. 18970 - 18976]
[4]Wu, Shaonan; Wang, Zhuo; Bao, Yinwei; Chen, Chen; Liu, Kun; Zhu, Bolin [Chemical Communications, 2020, vol. 56, # 32, p. 4408 - 4411]

41
[ 25309-64-2 ]
[ 1639128-68-9 ]
[ 1616514-68-1 ]

Yield	Reaction Conditions	Operation in experiment
37%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In N,N-dimethyl-formamide; at 80℃;Inert atmosphere;	General procedure: To a round-bottom flask were charged with an N?-Boc-N-aryl hydrazine 7 or 14 (48 mmol), 4-substituent iodobenzene 8 (40 mmol), CuI (0.78 g, 4 mmol), 1,10-phenanthroline (1.44 g, 8 mmol), Cs2CO3 (15.64 g, 48 mmol) and 40 mL of dry DMF at room temperature. The reaction mixture was degassed, charged with N2 gas and heated to 80 C. After 4-5 h, the resulting mixture was cooled to room temperature, diluted with ethyl acetate (100 mL), filtered. The filtrate was then washed twice with brine (2×100 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, The residue was purified by flash chromatography with a mixture of petroleum ether and ethyl acetate as an eluent to afford the desired product, which was recrystallized from a mixture of petroleum ether and ethyl acetate to give the desired crystals 9 or 15.

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 4952 - 4963
[2]Tetrahedron,2016,vol. 72,p. 2186 - 2195

42
[ 825-56-9 ]
[ 25309-64-2 ]
[ 113583-80-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With copper(II) oxide; potassium carbonate; triphenylphosphine; In diethylene glycol dimethyl ether; for 12h;Reflux; Green chemistry;	A 50 mL round-bottomed flask was charged with 2-phenyl-1,3,4-oxadiazole (1a; 510 mg, 3.5 mmol), 4-ethylphenyl iodide (2a; 1160 mg,5.0 mmol), nanoparticulate CuO (40 mg, 10%), Ph3P (395 mg, 30mol%), K2CO3 (690 mg, 10 equiv), and diglyme (15 mL). The mixture was stirred under reflux for 12 h until the starting materials were consumed (TLC). The mixture was then allowed to cool and extracted with EtOAc (2 × 30 mL). The CuO nanoparticles were removed centrifugation, washed with H2O, and dried in an oven at 120 C for 3 h. Concentration of the extract in vacuo followed by column chromatography (silica gel) gave oxadiazole 4aa; yield: 742 mg (85%). When the recovered CuO nanoparticles were reused, the yields for the second and third cycles were 82% (715 mg) and 78% (681 mg), respectively.

Reference： [1]Synthesis,2015,vol. 47,p. 2831 - 2838

43
[ 91-21-4 ]
[ 25309-64-2 ]
[ 1057280-52-0 ]

Yield	Reaction Conditions	Operation in experiment
79%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate; CyJohnPhos In toluene at 100℃; for 12h;	General Procedure: General procedure: The substrates were prepared by following a modified reportedprocedure.5 A mixture of Pd2(dba)3 (3 mol %), ligand (2-(dicyclohexylphosphino)biphenyl) (8mol %) and 15 mL of dry toluene were placed in an oven-dried tube. The tube was sealed andthe solution was degassed with bubbling argon for 1 h. Aryl halide (1.0 equiv), 1,2,3,4-tetrahydroisoquinolines (1.2 equiv), and t-BuONa (1.4 equiv) were added sequentially. Thenthe reaction mixture was heated at 100 °C for 12 h. The reaction mixture was cooled to roomtemperature, quenched by adding water, and extracted with ethyl acetate. The organic layer wasdried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product waspurified by column chromatography on silica gel using hexanes/ethyl acetate as the eluent toafford the desired products.
35%	With potassium phosphate; copper(l) iodide; ethylene glycol In isopropyl alcohol at 85 - 90℃; for 24h; Schlenk technique; Inert atmosphere;
	With potassium phosphate; copper(l) iodide; ethylene glycol In isopropyl alcohol at 20℃; Inert atmosphere;	General procedure for the preparation of N-aryltetrahydroisoquinolines General procedure: A mixture of CuI (10 mmol%) and K3PO4 (3.0 equiv.) was taken in a two necked round bottom flask evacuated and backfilled with nitrogen and fitted on oil bath. 2-Propanol (10 mL), ethylene glycol (1.1 mL), 1,2,3,4-tetrahydroisoqunoline (15 mmol, 2.0mL) and aryl iodide (10 mmol, 1.12 mL) were added successively by microsyring at rt. The reaction mixture was heated at 80-90 oC with stirring for 24-36 h. After the completion of the reaction was allowed to cool at rt. Diethyl ether (20 mL) and water (20 mL) was added to reaction mixture. The organic layer was extracted by diethyl ether (2 × 20mL). The combined organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed by rotary evaporator and the crude product was purified by column chromatography on silica gel with a mixture of hexane/ethyl acetate as eluent to afford an analytically pure sample of substrates 1.

With potassium phosphate; copper(l) iodide In ethylene glycol; isopropyl alcohol Inert atmosphere; Schlenk technique; Reflux;

Reference： [1]Guo, Bin; Xu, Hai-Chao [Beilstein Journal of Organic Chemistry, 2021, vol. 17, p. 2650 - 2656]
[2]Chen, Zhi-Hao; Gao, Pei-Sen; Mei, Tian-Sheng; Sun, Bing; Wang, Zhen-Hua; Weng, Xin-Jun; You, Shu-Li; Zheng, Chao [Angewandte Chemie - International Edition, 2020, vol. 59, # 35, p. 15254 - 15259][Angew. Chem., 2020, vol. 132, # 35, p. 15366 - 15371,6]
[3]Yadav, Arvind K.; Yadav, Lal Dhar S. [Tetrahedron Letters, 2015, vol. 56, # 48, p. 6696 - 6699]
[4]Li, Zhuohua; Ma, Pengju; Tan, Yongzhu; Liu, Yufei; Gao, Min; Zhang, Yujun; Yang, Bo; Huang, Xuan; Gao, Yuan; Zhang, Junmin [Green Chemistry, 2020, vol. 22, # 3, p. 646 - 650]

44
[ 25309-64-2 ]
[ 3956-07-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 4-ethyl-1-iodobenzene With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); water In ethyl acetate at 60℃; for 8h; Stage #2: With ammonium hydroxide; iodine In ethyl acetate; acetonitrile at 60℃; for 12h;

Reference： [1]Shimokawa, Shohei; Kawagoe, Yuhsuke; Moriyama, Katsuhiko; Togo, Hideo [Organic Letters, 2016, vol. 18, # 4, p. 784 - 787]

45
[ 25309-64-2 ]
[ 768-60-5 ]
[ 63221-88-5 ]

Yield	Reaction Conditions	Operation in experiment
87.7%	With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 12h;Schlenk technique;	General procedure: A 100 mL Schlenk flask was charged with 2-bromopyridine (1.1 mmol), phenylacetylene (0.92 mmol), Cs2CO3 (1.84 mmol), 1-Pd (0.003 mmol based on Pd), DMF (6 mL) and the reaction mixture was stirred at 100 C under air atmosphere for 12 h. The mixture was cooled to the room temperature; the solid was removed by filtration and washed twice with DMF (3 mL). The filtrate was collected, dried and the residue was extracted with ethyl acetate (3 x 3 mL) followed by purification with silica gel chromatography (petroleum ether) to give a corresponding product.

Reference： [1]Catalysis science and technology,2016,vol. 6,p. 2050 - 2054
[2]Journal of Catalysis,2016,vol. 344,p. 445 - 454

46
[ 25309-64-2 ]
[ 772-38-3 ]
C₂₀H₂₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 12h;Schlenk technique;	General procedure: A 100 mL Schlenk flask was charged with 2-bromopyridine (1.1 mmol), phenylacetylene (0.92 mmol), Cs2CO3 (1.84 mmol), 1-Pd (0.003 mmol based on Pd), DMF (6 mL) and the reaction mixture was stirred at 100 C under air atmosphere for 12 h. The mixture was cooled to the room temperature; the solid was removed by filtration and washed twice with DMF (3 mL). The filtrate was collected, dried and the residue was extracted with ethyl acetate (3 x 3 mL) followed by purification with silica gel chromatography (petroleum ether) to give a corresponding product.

Reference： [1]Catalysis science and technology,2016,vol. 6,p. 2050 - 2054
[2]Journal of Catalysis,2016,vol. 344,p. 445 - 454

47
[ 25309-64-2 ]
[ 17078-76-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2: copper(l) iodide; sodium iodide; Trimethylenediamine / pentan-1-ol / 20 h / 130 °C / Inert atmosphere; Schlenk technique; Sealed tube

Reference： [1]Buendia, Julien; Grelier, Gwendal; Darses, Benjamin; Jarvis, Amanda G.; Taran, Frédéric; Dauban, Philippe [Angewandte Chemie - International Edition, 2016, vol. 55, # 26, p. 7530 - 7533][Angew. Chem., 2016, vol. 128, # 26, p. 7656 - 7659]

48
[ 25309-64-2 ]
[ 5467-74-3 ]
[ 58743-79-6 ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 7530 - 7533
Angew. Chem.,2016,vol. 128,p. 7656 - 7659,4

49
[ 25309-64-2 ]
2-phenyl-N-(quinolin-8-yl)acetamide [ No CAS ]
2-(4,4''-diethyl[1,1':3',1''-terphenyl]-2'-yl)-N-(quinolin-8-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With silver(I) acetate; palladium diacetate; In toluene; at 110℃; for 24h;Inert atmosphere;	General procedure: An appropriate phenylacetamide (0.12 mmol, 1 equiv), an appropriate iodo compound (0.48 mmol, 4 equiv), Pd(OAc)2 (2.7 mg, 10 mol%), and AgOAc (50 mg, 0.3 mmol, 2.5 equiv) in anhydrous toluene (3 mL) was heated at 110 C for 24 h under a nitrogen atmosphere. After the reaction period, the solvent was evaporated in vacuo to afford a crude reaction mixture. Purification of the crude reaction mixture by column chromatography furnished the corresponding arylated products 4a-q/7a-f (bis arylation products), 3o,r/6a,b/8e,f/9a,b (mono arylation products) (see corresponding Tables/Schemes for specific examples and reaction conditions).

Reference： [1]Tetrahedron,2016,vol. 72,p. 5886 - 5897

50
[ 25309-64-2 ]
2-(3,4-dimethoxyphenyl)-N-(quinolin-8-yl)acetamide [ No CAS ]
2-(4'-ethyl-4,5-dimethoxy[1,1'-biphenyl]-2-yl)-N-(quinolin-8-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With silver(I) acetate; palladium diacetate; In toluene; at 110℃; for 24h;Inert atmosphere;	General procedure: An appropriate phenylacetamide (0.12 mmol, 1 equiv), an appropriate iodo compound (0.48 mmol, 4 equiv), Pd(OAc)2 (2.7 mg, 10 mol%), and AgOAc (50 mg, 0.3 mmol, 2.5 equiv) in anhydrous toluene (3 mL) was heated at 110 C for 24 h under a nitrogen atmosphere. After the reaction period, the solvent was evaporated in vacuo to afford a crude reaction mixture. Purification of the crude reaction mixture by column chromatography furnished the corresponding arylated products 4a-q/7a-f (bis arylation products), 3o,r/6a,b/8e,f/9a,b (mono arylation products) (see corresponding Tables/Schemes for specific examples and reaction conditions).

Reference： [1]Tetrahedron,2016,vol. 72,p. 5886 - 5897

51
[ 25309-64-2 ]
[ 2488-14-4 ]
N-α-boc-1-(4-ethylphenyl)-L-histidine methyl ester [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 8937 - 8941

52
[ 10220-22-1 ]
[ 25309-64-2 ]
1-(4-ethylphenyl)pyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With copper(l) iodide; In N,N-dimethyl-formamide; at 100℃; for 24h;	The 177 mu L (1.0mmol) 4- ethyl monoiodo-benzene, 167 mu L (2.0mmol) tetrahydrofurfuroxy pyrrolizinone, 100 mg sodium base montmorillonite clay, 0.0390g (0.2mmol) cuprous iodide, 0.5317g (2.5mmol) adding potassium phosphate 5mLN, in N-dimethyl formamide, 100 C reaction 24 hours, other steps of the embodiment 1 the same, to obtain a liquid N-(4-ethyl-phenyl) pyrrolidine, its yield is 75%, of the soil sodium Kimon escapes centrifugal separation to obtain the percent recovery of copper in 65%.

Reference： [1]Patent: CN104016897,2016,B .Location in patent: Paragraph 0023

53
[ 25309-64-2 ]
tert-butyl (E)-(2-(4-(1-(4-hydroxyphenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-1-en-1-yl)phenoxy)ethyl)carbamate [ No CAS ]
tert-butyl (Z)-(2-(4-(2-(4-ethylphenyl)-1-(4-hydroxyphenyl)but-1-en-1-yl)phenoxy)ethyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide; In 2-methyltetrahydrofuran; water; at 85℃; for 3h;Inert atmosphere;	Step-1: Synthesis of tert-butyl (Z)-(2-(4-(2-(4-ethylphenyl)-l-(4-hydroxyphenyl)but-l-en-l- yl)phenoxy )ethyl)carbamate To a stirred solution of tert-butyl (E)-(2-(4-(l-(4-hydroxyphenyl)-2-(4,4,5,5-tetramethyl- l ,3,2-dioxaborolan-2-yl)but-l-en-l-yl)phenoxy)ethyl)carbamate (1.3 g, 2.55 mmol, Example- 46, Step-1) in 2-methyl THF (15 mL), l-iodo-4-ethylbenzene (0.651 mg, 2.8 mmol), 4M aqueous KOH (2 mL) and Pd(PPh3)2Cl2 (89 mg, 0.127 mmol) were added and the mixture was degassed with nitrogen for 15 min and heated at 85 C for 3 h. Upon completion, the reaction mixture was diluted with EtOAc. The organic layer was washed with water followed by brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (2:8 EtOAc in n- hexane) to give title compound (0.5 g, 40%).

Reference： [1]Patent: WO2016/196342,2016,A1 .Location in patent: Page/Page column 112

54
[ 64-18-6 ]
[ 25309-64-2 ]
[ 637-44-5 ]
[ 742699-27-0 ]

Yield	Reaction Conditions	Operation in experiment
59%	With bis-triphenylphosphine-palladium(II) chloride; acetic anhydride; triethylamine; In toluene; at 30 - 80℃;Inert atmosphere;	General procedure: Phenylpropiolic acid (1 mmol), Pd(OAc)2 (3 mol%) and DPPM (3 mol%) were transferred into an oven-dried tube which was filled with nitrogen and equipped with a string bar. Then toluene (2.0 mL), iodobenzene (1.0 mmol), and Et3N (5.0 mmol) were added via a syringe. Then a mixture of formic acid (2.0 mmol) and acetic anhydride (2.0 mmol), which was stirred at 30 C for 1.0 h, added into the reaction tube. The final mixture was stirred at 80 C for 10-14 h. After the reaction was complete, the reaction mixture was filtered and concentrated, then column chromatography on silica gel (petroleum ether/ethyl acetate 50:1) to give the pure product.

Reference： [1]Journal of Organometallic Chemistry,2017,vol. 838,p. 9 - 11

55
[ 1493-13-6 ]
[ 25309-64-2 ]
[ 108-67-8 ]
(4-ethylphenyl)(2,4,6-trimethylphenyl)iodonium triflate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0℃; for 2h;Inert atmosphere; Sealed tube;	General procedure: The reaction was generally performed with 2.0 equivalents of TfOH. m-CPBA (65%active oxidant, 2.6 mmol) and aryl iodide (2.3 mmol) were dissolved in DCM (20 mL)in a sealed tube. The arene (2.6 mmol) was added and the solution was cooled to 0 oC,followed by dropwise addition of TfOH (4.6 mmol), and resulted in a colouredsolution. The reaction mixture was stirred for about 2 h, subsequently concentratedunder vacuum. Et2O was added and the mixture was stirred at room temperature for30 mins to precipitate out an off-white solid.

Reference： [1]Tetrahedron,2017,vol. 73,p. 3591 - 3595

56
[ 25309-64-2 ]
[ 5467-53-8 ]

Reference： [1]Patent: WO2008/112368,2008,A2

57
[ 25309-64-2 ]
[ 53661-18-0 ]

Reference： [1]Chinese Journal of Chemistry,2018,vol. 36,p. 1003 - 1006

58
[ 603-76-9 ]
[ 25309-64-2 ]
benzene-1,3,5-triyl triformate [ No CAS ]
C₂₇H₂₆N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With bis-triphenylphosphine-palladium(II) chloride; formic acid; triethylamine; tris-(o-tolyl)phosphine; In dimethyl sulfoxide; at 70℃; for 24h;	General procedure: PdCl2(PPh3)2 (0.1 mmol), P(o-tolyl)3 (0.1 mmol), TFben(0.5 mmol) and indole (1.0 mmol) were transferred into an ovendriedtube (15 mL), which was evacuated and backfilled withN2(5x). DMSO (2 mL), aryl iodide (1.2 mmol), Et3N (1 mmol) andHCO2H (1.5 mmol) were added into the tube via syringe. The reactionmixture was stirred at 70 C for 24 h. After the reaction wascomplete, the mixture was filtrated and extracted with DCM. Thecombined organic layers were washed with H2O and brine, driedover anhydrous Na2SO4, and then concentrated under vacuum.The crude product was purified by column chromatography on silicagel (petroleum ether/ethyl acetate = 20/1) to afford the product.

Reference： [1]Journal of Catalysis,2018,vol. 362,p. 74 - 77

59
[ 775351-57-0 ]
[ 25309-64-2 ]
4'-ethyl-4-fluoro-[1,1'-biphenyl]-3-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 9513 - 9533

60
[ 504-29-0 ]
[ 25309-64-2 ]
[ 214958-27-7 ]

Yield	Reaction Conditions	Operation in experiment
92%		Add 3 mL of water in a 25 mL reaction flask. 30 muL Tween, 0.5 mmol <strong>[25309-64-2]1-ethyl-4-iodobenzene</strong>,1.5 mmol NBS and 0.05 mmol AIBN, After reacting at 60 C for 4 h, 2.0 mmol of sodium hydrogencarbonate and 0.5 mmol of alpha-aminopyridine were added. After reacting at 80 C for 2 h, after the reaction is completed, Add ethyl acetate and extract with saturated brine. Concentrated organic phase, Column chromatography gave 147 mg of a white solid. The yield was 92%.
84%		In a 25 mL reaction flask, 3 mL of water, 0.5 mmol of <strong>[25309-64-2]1-ethyl-4-iodobenzene</strong>, 1.0 mmol of DBH, and0.05mmol TBHP, after reacting at 60 C for 4h, add 2.0mmol sodium bicarbonate and 0.5mmol alpha-aminopyridine at 80 CAfter reacting for 2 hours, the reaction mixture was completed, ethyl acetate was added thereto, and brine was added and the organic phase was concentrated.Column chromatography gave 134 mg of a white solid.The yield was 84%.

Reference： [1]Patent: CN108822105,2018,A .Location in patent: Paragraph 0095; 0096; 0097; 0098
[2]Patent: CN108822106,2018,A .Location in patent: Paragraph 0093; 0094; 0095; 0096

61
[ 124-38-9 ]
[ 25309-64-2 ]
[ 25309-65-3 ]

Yield	Reaction Conditions	Operation in experiment
43%Chromat.	With 1,4-diaza-bicyclo[2.2.2]octane; copper(I) oxide; phenylsilane; ammonia; In 1-methyl-pyrrolidin-2-one; at 130℃; under 2280.15 Torr; for 24h;Sealed tube;	General procedure: Under nitrogen atmosphere, Cu2O (10 mol %), DABCO (25 mol %), and a stirring bar were added into a 10 mL oven-dried sealed glass tube (as shown in Figure S1). Then NMP (0.5 mL), aryl iodides (0.125 mmol, 1.0 equiv.) and PhSiH3 (0.75 mmol, 6 equiv.) were injected by syringe. The tube was then sealed and CO2 (0.67 mmol, 5.4 equiv., 15 mL) as well as NH3 (0.67 mmol, 5.4 equiv., 15 mL) were injected by syringe after N2 was removed under vacuum. Finally, the mixture was stirred for 24 hr in a pre-heated-to-130 C alloyed block. After the reaction was finished, the tube was cooled to room temperature and the pressure was carefully released. The yield of were measured by GC analysis using dodecane as the internal standard or by flash chromatography on silica gel (petroleumether/ethyl acetate).

Reference： [1]Chem,2018,vol. 4,p. 2883 - 2893

62
[ 106-31-0 ]
[ 578-66-5 ]
[ 25309-64-2 ]
3-(4-ethylphenyl)-N-(quinolin-8-yl)butanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With silver(I) acetate; palladium diacetate; In neat (no solvent); at 110℃; for 24h;Inert atmosphere;	General procedure: A mixture of anhydride (2,1 equiv), DG (8-aminoquinoline, 3a, 1 equiv), ArI (4-6 equiv), Pd(OAc)2 (10 mol%) and AgOAc (2.2 equiv) was heated at 110 C for an appropriate time (2-24 h, see the corresponding Tables/Schemes for exact time and other specific conditions). Then, reaction mixture was cooled to rt, filtered on celite (EtOAc was used as a washing solvent) and the filtrate was treated with aq. NaHCO3 solution and then, extracted using EtOAc. The combined organic layers were dried over anhydrous Na2SO4 and evaporated to afford the crude reaction mixture. Then, the crude reaction mixture was subjected to the column chromatographic purification (EtOAc:Hexane 20:80) to give the corresponding C-H arylated product (see the respective Tables/Schemes for the specific entries).

Reference： [1]Tetrahedron,2019,vol. 75,p. 1246 - 1257

63
[ 20880-92-6 ]
[ 25309-64-2 ]
C₂₀H₂₈O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With copper(l) iodide; sodium t-butanolate In N,N-dimethyl-formamide at 20℃; for 24h; Schlenk technique; Inert atmosphere; Molecular sieve;

Reference： [1]Chen, Zhixiang; Jiang, Yongwen; Zhang, Li; Guo, Yinlong; Ma, Dawei [Journal of the American Chemical Society, 2019, vol. 141, # 8, p. 3541 - 3549]

64
[ 696-63-9 ]
[ 25309-64-2 ]
(4-ethylphenyl)(4-methoxyphenyl)sulfane [ No CAS ]

Reference： [1]ACS Catalysis,2019,vol. 9,p. 1630 - 1634

65
[ 25309-64-2 ]
C₁₆H₁₅F₇N₂O [ No CAS ]
C₂₄H₂₃F₇N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%		General procedure: To a large microwave tube (Biotage, 10-20 mL) equipped with a stir bar was added Pd(OAc)2(23.4 mg, 0.10 mmol, 10 mol %), S-1 (400 mg, 1.04 mmol, 1 equiv), cesium pivalate (731 mg,3.12 mmol, 3 equiv), aryl iodide (2-3 equiv) and anhydrous tert-amyl alcohol (9.6 mL). The capwas crimped and the vessel was flushed with nitrogen. The microwave tube was heated withfollowing parameters: 1 min pre-stirring, followed by a ramp (normal) to 180 C and held attemperature for 30 to 50 min. Hydrazine (500 muL of 35% aqueous) was added to the reaction andallowed to stir at 60 C for 1 hr or at room temperature overnight. The tert-amyl alcohol wasremoved en vacuo and the remaining residue dissolved with EtOAc, filtered through a plug ofcelite, and concentrated en vacuo. The crude reaction was purified via flash columnchromatography with EtOAc/Heptanes.

Reference： [1]Synlett,2019,vol. 30,p. 417 - 422

66
[ 2550-26-7 ]
[ 25309-64-2 ]
4-(4-ethylphenyl)-4-phenylbut-3-en-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With 4,5-Diazafluoren-9-one; oxygen; cesium acetate; palladium diacetate; In dimethyl sulfoxide; at 100℃; for 16h;Sealed tube;	General procedure: A tube (30 mL) equipped with a magnetic stirring bar was charged with 1 (1.5 mmol), 2 (5.25 mmol), Pd(OAc)2 (10 mol%), L1 (10 mol%), and CsOAc (6.0 mmol) in DMSO (1.5 mL), then the tube was sealed, purged with O2, and the mixture was stirred at 100 C for 16 h. At the end of the reaction, the mixture was partitioned between EtOAc (30mL) and H2O (30 mL). The organic layer was separated, and the aqueous layer was extracted further with EtOAc (3 × 30 mL). The combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. Then, the crude mixture was purified by column chromatography (silica gel; n-hexane/EtOAc) to afford the desired product.

Reference： [1]Synthesis,2019,vol. 51,p. 1455 - 1465

67
[ 25309-64-2 ]
[ 1180819-69-5 ]
4-(1,3-dioxoisoindolin-2-yl)-3-(4-ethylphenyl)-N-(quinolin-8-yl)butanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With silver(I) acetate; palladium diacetate; In toluene; at 110℃; for 24h;Inert atmosphere;	General procedure: A mixture of an appropriate unnatural amino acid carboxamide 6 (0.15-0.2 mmol, 1 equiv), an appropriate aryl iodide (5 equiv), Pd(OAc)2 (10 mol%) and AgOAc (2.5 equiv) in anhydrous toluene (2-3 mL) was heated at 110 C for 15-24 h under a nitrogen atm or in a sealed tube. After the reaction period, the reaction mixture was concentrated under reduced pressure to afford a crude reaction mixture, which was purified by column chromatography on neutral alumina or silica gel (eluent EtOAc:hexane) to give the corresponding arylated amino acid (see the respective Schemes/Tables for the specific entries). 3.4.11. 4-(1,3-Dioxoisoindolin-2-yl)-3-(4-ethylphenyl)-N-(quinolin-8-yl)butanamide (8n). The compound 8n was obtained after purification by columnchromatography on silica gel (EtOAc:hexane 40:60) as a yellowcolor solid (68 mg, 73%); Rf (40% EtOAc/hexane) 0.75; mp:138e140 C; IR (DCM): 3348, 2965, 1713, 1326, 721 cm1; 1H NMR(400 MHz, CDCl3): dH 9.81 (1H, br. s), 8.80 (1H, dd, J1 4.2,J2 1.4 Hz), 8.47 (1H, d, J 7.4 Hz), 8.15 (1H, d, J 8.0 Hz), 7.64 (2H,dd, J1 5.4, J2 3.1 Hz), 7.53 (2H, dd, J1 5.4, J2 3.0 Hz), 7.46 (1H,dd, J1 8.2, J2 4.2 Hz), 7.42e7.38 (1H, m), 7.34 (2H, d, J 8.0 Hz),7.14 (2H, d, J 7.9 Hz), 4.08e3.95 (3H, m), 3.00 (2H, d, J 5.7 Hz),2.58 (2H, q, J 7.6 Hz), 1.16 (3H, t, J 7.6 Hz); 13C NMR (CDCl3,101 MHz): dC 169.4, 168.4, 148.0, 143.1, 138.1, 136.3, 134.2, 133.7,131.9, 128.2, 127.7, 127.7, 127.3, 123.0, 121.5, 121.3, 116.3, 43.4, 42.2,40.5, 28.4, 15.4; HRMS (ESI) calcd for C29H26N3O3 [MH] 464.1974found 464.1994.

Reference： [1]Tetrahedron,2019,vol. 75,p. 2447 - 2465

68
[ 25309-64-2 ]
11-(1,3-dioxoisoindolin-2-yl)-N-(quinolin-8-yl)undecanamide [ No CAS ]
11-(1,3-dioxoisoindolin-2-yl)-3-(4-ethylphenyl)-N-(quinolin-8-yl)undecanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With silver(I) acetate; palladium diacetate; In toluene; at 110℃; for 24h;Inert atmosphere;	General procedure: A mixture of an appropriate unnatural amino acid carboxamide 6 (0.15-0.2 mmol, 1 equiv), an appropriate aryl iodide (5 equiv), Pd(OAc)2 (10 mol%) and AgOAc (2.5 equiv) in anhydrous toluene (2-3 mL) was heated at 110 C for 15-24 h under a nitrogen atm or in a sealed tube. After the reaction period, the reaction mixture was concentrated under reduced pressure to afford a crude reaction mixture, which was purified by column chromatography on neutral alumina or silica gel (eluent EtOAc:hexane) to give the corresponding arylated amino acid (see the respective Schemes/Tables for the specific entries). 3.4.41. 11-(1,3-Dioxoisoindolin-2-yl)-3-(4-ethylphenyl)-N-(quinolin-8-yl)undecanamide (13d). The compound 13d was obtained after purification by column chromatography on silica gel (EtOAc:hexane 40:60) as a yellowcolor liquid (58 mg, 69%); Rf (40% EtOAc/hexane) 0.5; IR (DCM):2927, 1710, 1523, 1395, 719 cm1; 1H NMR (400 MHz, CDCl3) dH 9.69(1H, br. s), 8.78e8.74 (2H, m), 8.15 (1H, d, J 8.2 Hz), 7.85 (2H, dd,J1 5.3, J2 3.0 Hz), 7.71 (2H, dd, J1 5.4, J2 3.1 Hz), 7.54e7.43 (3H, m), 7.21 (2H, d, J 7.8 Hz), 7.13 (2H, d, J 7.8 Hz), 3.66 (2H, t,J 7.3 Hz), 3.29e3.25 (1H, m), 2.84 (2H, d, J 7.4 Hz), 2.60 (2H, q,J 7.6 Hz), 1.81e1.58 (4H, m), 1.32e1.17 (13H, m); 13C NMR (CDCl3,101 MHz): dC 170.6, 168.4, 148.0, 142.1, 141.6, 138.2, 136.3, 134.5,133.8, 132.2, 128.0, 127.9, 127.9, 127.4, 123.1, 121.5, 121.3, 116.4, 45.9,42.2, 38.0, 36.2, 29.5, 29.3, 29.1, 28.6, 28.4, 27.4, 26.8, 15.4; HRMS(ESI) calcd for C36H40N3O3 [MH] 562.3070 found 562.3087.

Reference： [1]Tetrahedron,2019,vol. 75,p. 2447 - 2465

69
[ 25309-64-2 ]
[ 31827-94-8 ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 2520 - 2527

70
[ 25309-64-2 ]
[ 31699-14-6 ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 2520 - 2527

71
[ 25309-64-2 ]
[ 40137-29-9 ]
2-chloro-6-ethylanthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With trifluorormethanesulfonic acid; palladium diacetate; silver trifluoroacetate; acetic acid; glycine; at 100℃; for 24h;Sealed tube;	General procedure: A sealed tube with magnetic stir bar was charged with substrate 1 (0.24 mmol), glycine (0.1 mmol, 7.5 mg), Pd(OAc)2 (0.02 mmol, 4.45 mg), AgTFA (0.24 mmol, 53.01 mg) and 2 (0.2 mmol) under air. After addition of AcOH (2 mL) as solvent, TfOH (0.1 mmol, 15.0 mg) was added. The reaction mixture was allowed to stir at 100 C for 24 hours. Upon completion, the reaction mixture was cooled to room temperature, diluted with DCM, and then extracted with saturated NaHCO3 aqueous solution. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel using PE as the eluent to afford the desired products.

Reference： [1]Tetrahedron,2019,vol. 75,p. 4031 - 4041

72
[ 201230-82-2 ]
methyl 2-(dimethyl(oxo)-λ⁶-sulfanylidene) acetate [ No CAS ]
[ 25309-64-2 ]
methyl 2-(dimethyl(oxo)-λ⁶-sulfanylidene)-3-(4-ethylphenyl)-3-oxopropanoate [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 5310 - 5314

73
[ 98-01-1 ]
[ 25309-64-2 ]
[ 121-44-8 ]
[ 57806-75-4 ]

Yield	Reaction Conditions	Operation in experiment
63%	With Wilkinson?s catalyst; 1,3-bis-(diphenylphosphino)propane; water; In tetrahydrofuran; at 140℃; for 12h;Inert atmosphere; Sealed tube;	General procedure: Rh(PPh3)3Cl (2.5 mol%) and DPPP (0.04 mmol) were transferred into an oven-dried tube(15 mL), which was evacuated and backfilled with N2 (5x). THF(2 mL), H2O (1 mmol), aryl iodides (1.2 mmol), furfural (1 mmol)and amine (1.8 mmol) were added into the tube via syringe and sealed with Teflon plug. The reaction mixture was stirred at 140 C for 12 h. After the reaction was complete, the mixture was concentrated by rotary evaporation. The crude product was purified by column chromatography (EA/PE = 1/20) on a silica gel to afford the desired product.

Reference： [1]Journal of Catalysis,2020,vol. 381,p. 215 - 221

74
[ 67-47-0 ]
[ 25309-64-2 ]
C₁₄H₁₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 1,3-bis-(diphenylphosphino)propane; sodium carbonate; In 2-methyltetrahydrofuran; at 125℃; for 24h;Molecular sieve; Inert atmosphere; Sealed tube;	General procedure: Rh(cod)2BF4(6 mol%), DPPP (0.09 mmol), Na2CO3 (1 mmol) and 4A MS (SiO2,powder, 150 mg) were transferred into an oven-dried tube (15 mL), which was evacuated and backfilled with N2 (5x). 2-Methyltetrahydrofuran (2.5 mL), alkyl or aryl iodide (1 mmol),HMF (1.2 mmol) were added into the tube via syringe and sealed with Teflon plug. The reaction mixture was stirred at 125 C for24 h. After the reaction was complete, the mixture was concentrated by rotary evaporation. The crude product was purified by column chromatography (EA/PE = 1/20) on a silica gel to afford the desired product.

Reference： [1]Journal of Catalysis,2020,vol. 381,p. 215 - 221

75
[ 25309-64-2 ]
[ 2978-58-7 ]
4-(4-ethylphenyl)-2-methylbut-3-yn-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;
90%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;

Reference： [1]Ying, Jun; Le, Zhengjie; Wu, Xiao-Feng [Organic Letters, 2020, vol. 22, # 1, p. 194 - 198]
[2]Le, Zhengjie; Zhu, Yiwen; Bao, Zhi-Peng; Ying, Jun; Wu, Xiao-Feng [Advanced Synthesis and Catalysis, 2021, vol. 363, # 7, p. 1878 - 1881]

76
[ 21573-10-4 ]
[ 25309-64-2 ]
1-cyclopropyl-2-(4-ethylphenyl)-1,3-butanedione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With copper(l) iodide; potassium carbonate; L-proline; In dimethyl sulfoxide; at 90℃; for 18h;Inert atmosphere;	To a three-necked flask was added K2CO3 (2.76 g, 20 mmol), CuI(190 mg,1 mmol), L-Proline (230 mg, 2 mmol) and DMSO, then 1-cyclopropylbutane-1,3-dione (1.17 mL, 10 mmol) and <strong>[25309-64-2]1-ethyl-4-iodobenzene</strong>(0.724 mL, 5 mmol) were added to the mixture, which werestirred at 90 C for 18 h under N2 protection. The reaction mixture wasdissolved in water, and then extracted with ethyl acetate (3*15 mL),washed with saturated NaCl, and dried over Na2SO4. Flash columnchromatography (petroleum ether : ethyl acetate = 70:1) afforded 1(320 mg, 28.0%) as pale-yellow oily liquid.1H NMR (300 MHz, CDCl3) delta(ppm): delta 17.03 (s, 1H), 7.28 - 7.19 (m, 4H), 2.71 (t, J = 7.6 Hz, 2H),1.92 (s, 3H), 1.57 (tt, J = 7.9, 4.6 Hz, 1H), 1.30 (d, J = 7.6 Hz, 3H),1.16 (dt, J = 4.4, 3.2 Hz, 2H), 0.84 - 0.77 (m, 2H). HRMS (ESI)C15H18O2, [M + H]+ calculated = 231.1307; found = 231.1393.
14%	With copper(l) iodide; potassium carbonate; L-proline; In dimethyl sulfoxide; at 90℃; for 18h;Inert atmosphere;	Anhydrous K2CO3 (2.76 g, 20 mmol), L-proline (230 mg, 2 mmol),CuI (95mg, 0.5mmol), added to a 100ml three-necked reaction flask, protected by N2,DMSO (20 ml), 1-cyclopropyl-1,3, -butanedione (0.59 ml, 5 mmol),<strong>[25309-64-2]1-ethyl-4-iodobenzene</strong> (0.724 ml, 5 mmol) was magnetically stirred, the reaction temperature was 90 C., and the reaction was performed for 18 h. TLC monitoring (PE: EA = 20: 1).Work-up: After the reaction solution was cooled to room temperature, suction filtration was performed, and the filtrate was extracted with ethyl acetate (EA) (3 × 10 ml).The organic layers were combined, washed with saturated brine (3 × 10 ml), and dried over anhydrous Na 2 SO 4.Column chromatography after concentration. The eluent is PE: EA = 70: 1, and dried under vacuum.160 mg of a yellow solid was obtained with a yield of 14%.

Reference： [1]Bioorganic and medicinal chemistry,2020,vol. 28
[2]Patent: CN110615808,2019,A .Location in patent: Paragraph 0058-0062

77
[ 25309-64-2 ]
5-(3,5-dimethylisoxazole-4-yl)-2-methylaniline [ No CAS ]
C₂₀H₂₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82.2%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; DavePhos; In acetonitrile; at 80℃;Inert atmosphere;	4-Ethyl iodobenzene (348.0 mg, 1.5 mmol), 5- (3,5-dimethylisoxazole-4-)-2-methylaniline (202.1 mg, 1 mmol), Cs2CO3 (585.0 mg, 2.5 mmol ), Pd2 (dba) 3 (46.0 mg, 0.05 mmol) and Davephos (32.0 mg, 0.08 mmol) were added to the reaction tube, and 6 ml of acetonitrile was added as a solvent. After changing N2 three times, it was heated to 80 C and stirred overnight. After cooling to room temperature, the celite was filtered and concentrated, and the crude product was purified with a silica gel column (PE: EA = 20: 1) to obtain 250 mg of a light yellow viscous substance, namely the intermediate N-pyridine-2- (5- (3, 5-Dimethylisoxazole-4-)-2-methylaniline, yield: 82.2%. After N-ethylation reaction, compound 042 was obtained, and the operation was the same as Example 043.

Reference： [1]Patent: CN110960528,2020,A .Location in patent: Paragraph 0075; 0102-0105

78
[ 4406-77-3 ]
[ 25309-64-2 ]
[ 106-49-0 ]
[ 100-41-4 ]
4-ethyl-N-(p-tolyl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 75% 2: 20%	With nickel(II) iodide; potassium phosphate; 2,6-di-tert-butyl-4-methyl-phenol In 1,4-dioxane at 115℃; for 12h; Inert atmosphere; chemoselective reaction;

Reference： [1]Dhital, Raghu N.; Hashizume, Daisuke; Hu, Hao; Ishii, Rikako; Sato, Takuma; Sen, Abhijit; Takaya, Hikaru; Uozumi, Yasuhiro; Yamada, Yoichi M. A. [Organic Letters, 2020]

79
[ 25309-64-2 ]
[ 1225387-53-0 ]
1-(4-ethylphenyl)-1H-pyrazol-3-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With caesium carbonate; copper(ll) bromide In N,N-dimethyl-formamide at 180℃; for 0.5h; Microwave irradiation;	1 Step 1 General procedure: Copper(ll) bromide (0.1 eq.), CS2CO3 (1 eq.), DMF (0.4 M), the proper pyrazolamine (V, 1.4 eq.) and the proper commercially available halide (XXV, 1 eq.) were added sequentially to a MW tube and the reaction mixture was heated in a MW reactor at 180 °C for 30 min. The reaction mixture was loaded onto a pad of ScX resin (Si-TsOH), washed with MeOH and eluted with 0.7 M NH3 in MeOH. The crude was purified by flash chromatography to give the intermediate compound with general formula LXXXVI.

Reference： [1]Current Patent Assignee: AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO - A.C.R.A.F. - S.P.A. ENUNCIABILE ANCHE A.C.R.A.F. S.P.A. , ACRAF S.P.A. , ANGELINI S.P.A. - WO2020/178316, 2020, A1 Location in patent: Page/Page column 130

80
[ 25309-64-2 ]
[ 471-25-0 ]
[ 79135-69-6 ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-di(diphenylphosphino)-butane In dimethyl sulfoxide at 80℃; for 3h;

Reference： [1]Yu, Wentao; Zhu, Baiyao; Shi, Fuxing; Zhou, Peiqi; Wu, Wanqing; Jiang, Huanfeng [Angewandte Chemie - International Edition, 2021, vol. 60, # 3, p. 1313 - 1322][Angew. Chem., 2021, vol. 133, # 3, p. 1333 - 1342,10]

81
[ 90560-10-4 ]
[ 25309-64-2 ]
2-(4-ethylphenyl)-6-methoxybenzo[b]thiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With palladium diacetate; silver trifluoroacetate; trifluoroacetic acid In water at 20℃; for 48h; Inert atmosphere;	5.1.2. General procedure a for the synthesis of compounds 7a-o General procedure: To a suspension of 6-methoxybenzo[b]thiophene 6 (164 mg, 1mmol), CF3COOAg (331 mg, 1.5 mmol), trifluoroacetic acid (228 mg,0.15 mL, 2 mmol), the appropriate iodobenzene derivative (2.0 mmol)and Tween-80/H2O (2 mL, 2 wt%) was degassed under a stream of argonover 10 min. Pd(OAc)2 (11.2 mg, 0.05 mmol, 5 mol %) was added andthe mixture degassed again for 10 min, then stirred at room temperature for 48 h. After this time, the reaction mixture was diluted with EtOAc(10 mL), filtered on a pad of celite and the filtrate washed sequentiallywith water (5 mL) and brine (5 mL), dried over Na2SO4 and evaporatedunder reduced pressure. The crude residue was purified by flash columnchromatography on silica gel using a mixture of ethyl ether and petroleumether to afford the title compound.

Reference： [1]Romagnoli, Romeo; Preti, Delia; Hamel, Ernest; Bortolozzi, Roberta; Viola, Giampietro; Brancale, Andrea; Ferla, Salvatore; Morciano, Giampaolo; Pinton, Paolo [Bioorganic Chemistry, 2021, vol. 112]

82
[ 480-91-1 ]
[ 25309-64-2 ]
2-(4-ethylphenyl)isoindolin-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With copper (I) iodide; Cs₂CO₃; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 120℃; for 3h; Inert atmosphere;
	With tripotassium phosphate tribasic; copper (I) iodide

Reference： [1]Gao, Yuhan; Huang, Zhiliang; Lei, Aiwen; Yi, Hong; Yu, Mingming; Zhang, Lin; Zhang, Yingjie; Zhang, Yiyan [Green Chemistry, 2022, vol. 24, # 4, p. 1445 - 1450]
[2]Lai, Huifang; Xu, Jiexin; Lin, Jin; Zha, Daijun [Organic and Biomolecular Chemistry, 2021, vol. 19, # 35, p. 7621 - 7626]

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Precautionary Statements-General
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P321
P322
P330	Rinse mouth.
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P342	If experiencing respiratory symptoms:
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P378
P380	Evacuate area.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
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H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
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H280	Contains gas under pressure; may explode if heated
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H290	May be corrosive to metals
Health hazards
Code	Phrase
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H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
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H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 25309-64-2 ] {[proInfo.proName]}

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[ 25309-64-2 ] Synthesis Path-Upstream 1~21

[ 25309-64-2 ] Synthesis Path-Downstream 1~82

Related Functional Groups of [ 25309-64-2 ]

Aryls

Precautionary Statements-General

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[ 25309-64-2 ]