[ CAS No. 66107-32-2 ] {[proInfo.proName]}

Name: 66107-32-2|4-Cyanophenyl trifluoromethanesulfonate|98%
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Quality Control of [ 66107-32-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 66107-32-2 ]

Product Details of [ 66107-32-2 ]

CAS No. :	66107-32-2	MDL No. :	MFCD00973310
Formula :	C₈H₄F₃NO₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KKETVWGQXANCHL-UHFFFAOYSA-N
M.W :	251.18	Pubchem ID :	550182
Synonyms :

Safety of [ 66107-32-2 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P501-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405	UN#:	3265
Hazard Statements:	H314-H290	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 66107-32-2 ]

* 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 [ 66107-32-2 ]
Downstream synthetic route of [ 66107-32-2 ]

[ 66107-32-2 ] Synthesis Path-Upstream 1~4

1
[ 109-01-3 ]
[ 66107-32-2 ]
[ 34334-28-6 ]

Reference： [1] Synlett, 1999, # 10, p. 1559 - 1562

2
[ 15226-74-1 ]
[ 64-17-5 ]
[ 66107-32-2 ]
[ 7153-22-2 ]

Reference： [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 3, p. 419 - 425

3
[ 66107-32-2 ]
[ 3032-92-6 ]

Reference： [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 21, p. 4036 - 4052

4
[ 66107-32-2 ]
[ 126747-14-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; diisopropopylaminoborane; triethylamine; triphenylphosphine In tetrahydrofuran at 65℃; for 12 h; Inert atmosphere Stage #2: With methanol In tetrahydrofuran at 0℃; Inert atmosphere	General procedure: Triphenylphosphene (0.131 g, 0.5 mmol, 20 mol percent), p-iodoanisol (0.585 g, 2.5 mmol), and triethylamine (1.78 mL, 12.5 mmol) were added to a 50 mL round-bottomed flask equipped with a sidearm, condenser, and stir bar. This solution was then degassed by alternating vacuum and argon three times. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol percent) was then added under positive argon pressure. After stirring at room temperature for 15 min, diisopropylaminoborane (5 mL, 1 M solution in THF, 5 mmol) was added and the reaction mixture was degassed again by alternating vacuum and argon three times. The reaction solution was then heated to reflux. After 12 h of reflux the reaction was cooled to 0 °C and 6 mL of methanol was added through the condenser slowly (Caution: exothermic reaction with evolution of hydrogen). After 15 min of stirring all the solvent was removed under reduced pressure to yield a black solid. This solid was dissolved with sodium hydroxide (3 M, 8 mL) and subsequently washed with hexanes (3.x.10 mL). The aqueous layer was then cooled to 0 °C (ice bath) and acidified to pH <=1 with concentrated HCl, with the boronic acid usually precipitating out as a white solid. The aqueous fraction was then extracted with diethyl ether (3.x.10 mL). The organic fractions were combined, dried with magnesium sulfate and filtered. The solvent was then removed under reduced pressure yielding a white solid.

Reference： [1] Tetrahedron, 2011, vol. 67, # 3, p. 576 - 583

[ 66107-32-2 ] Synthesis Path-Downstream 1~88

1
[ 110-91-8 ]
[ 66107-32-2 ]
[ 10282-31-2 ]

Yield	Reaction Conditions	Operation in experiment
82%		EXAMPLE 17 N-(4-Cyanophenyl)morpholine STR18 General procedure A with 50.0 mg (0.199 mmol) of 4-cyanophenyltriflate and 26.0 μl (0.299 mmol) of morpholine gave N-(4-cyanophenyl)morpholine as a white solid (31 mg, 82% yield).

Reference： [1]Synthesis,1990,p. 1145 - 1147
[2]Tetrahedron Letters,1997,vol. 38,p. 6363 - 6366
[3]Organic Syntheses,2002,vol. 78,p. 23 - 23
[4]Patent: US5817877,1998,A
[5]Synlett,1999,p. 1559 - 1562
[6]Journal of Organic Chemistry,1997,vol. 62,p. 1268 - 1273
[7]Journal of Organic Chemistry,1997,vol. 62,p. 1264 - 1267

2
[ 111-34-2 ]
[ 66107-32-2 ]
[ 1443-80-7 ]
[ 127087-67-6 ]
[ 127087-66-5 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 3654 - 3655

3
[ 111-34-2 ]
[ 66107-32-2 ]
[ 453537-17-2 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triethylphosphite)nickel(0); N-Methyldicyclohexylamine; 1,2-bis-(diphenylphosphino)ethane; In toluene; at 100℃; for 18h;Sealed tube;	General procedure: A flame-dried Schlenk tube was charged sequentially with the corresponding aryl triflate, nickel catalyst (Ni[P(OPh)3]4 or Ni[P(OEt)3]4), diphosphine ligand (dppf or dppe), and Cy2NMe. The mixture was dissolved in toluene or 1,4-dioxane (~6mL mmol-1), followed by the addition of butyl vinyl ether. The reaction vessel was sealed, and stirred at 100 C for 18 h in a preheated oil bath. For the hydrolysis step, the reaction mixture was allowed to cool to room temperature (RT), and then treated with 6M HCl (~6mL mmol-1). The mixture was stirred vigorously at RT for 1 h. After dilution with Et2O (10 mL), the organic layer was separated and fused onto silica gel. Purification by flash column chromatography on silica gave the desired ketone products.

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 1481 - 1486
[2]Journal of the American Chemical Society,2012,vol. 134,p. 443 - 452
[3]Australian Journal of Chemistry,2015,vol. 68,p. 1842 - 1853
[4]Angewandte Chemie - International Edition,2017,vol. 56,p. 15441 - 15445
Angew. Chem.,2017,vol. 129,p. 15643 - 15647,5

4
[ 3195-78-6 ]
[ 66107-32-2 ]
[ 141172-00-1 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3558 - 3563

5
[ 114067-35-5 ]
[ 66107-32-2 ]
[ 97780-99-9 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 6511 - 6514

6
[ 66107-32-2 ]
[ 151-50-8 ]
[ 623-26-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 1118 - 1121

7
[ 66107-32-2 ]
[ 100-47-0 ]

Reference： [1]Chemistry Letters,1991,p. 2017 - 2018
[2]Organic Letters,2021,vol. 23,p. 9387 - 9392
[3]Tetrahedron Letters,1987,vol. 28,p. 1381 - 1384

8
[ 358-23-6 ]
[ 767-00-0 ]
[ 66107-32-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With pyridine; In dichloromethane; at 20℃;Inert atmosphere; Cooling with ice;	General procedure: To a flame-dried 25 mL round-bottom flask fitted with a rubber septum and equipped with a magnetic stir bar was added phenol (1.0 equiv). The contents were evacuated and backfilled three times with nitrogen. Anhydrous DCM (0.7 M) and distilled pyridine (4.2 equiv) were added via syringe and the stirred solution was cooled in an ice bath for 10 min. Triflic anhydride (1.4 equiv) was added dropwise over 5 min. The reaction was slowly warmed to room temperature. After 10-14 h, the reaction was diluted with Et2O (30 mL) and quenched with 1 M aqueous HCl (30 mL). The organic layer was extracted. The organic layer washed with water (2 x 25mL), then brine (25 mL), dried over MgSO4, filtered, and concentrated via rotary evaporation. The aryl triflate was purified by flash chromatography (gradient 2-20% EtOAc/hexanes over 45 column volumes.
	With pyridine; In dichloromethane; at 0 - 25℃; for 12h;Inert atmosphere;	General procedure: After phenols and pyridine were dissolved in dry DCM, triflic anhydridewas added slowly by syringe over 5 min at 0 C. Then the reaction mixture was allowed to bewarmed up to 25 C and further stirred at 25 C for 12 h. After the reaction mixture was quenche dwith water, the aqueous layer was extracted with CH2Cl2 and the combined organic layer was dried over Na2SO4 and then filtrated. The products were purified by regular flash chromatography (petroleumether/EtOAc mixtures) [10].
	With pyridine; In dichloromethane; at 0 - 25℃; for 12h;Inert atmosphere;	General procedure: Under N2 atmosphere, phenols and pyridine were dissolved in dry CH2Cl2, then, triflic anhydride was added slowly by syringe over 5 min at 0C. Then the reaction mixture was allowed to be warmed up to 25C and further stirred at 25C for 12 h. After the reaction mixture was quenched with water, the aqueous layer was extracted with CH2Cl2 and the combined organic layer was dried over Na2SO4 and then filtrated. The products were purified by regular flash chromatography (petroleum ether/EtOAc mixtures).1

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 472 - 480
[2]Tetrahedron,2003,vol. 59,p. 10295 - 10305
[3]Organic Letters,2005,vol. 7,p. 1169 - 1172
[4]Journal of Organic Chemistry,2018,vol. 83,p. 11178 - 11190
[5]European Journal of Organic Chemistry,2021,vol. 2021,p. 309 - 313
[6]Journal of Organic Chemistry,2004,vol. 69,p. 1137 - 1143
[7]Tetrahedron,2018,vol. 74,p. 3314 - 3317
[8]Journal of Medicinal Chemistry,1998,vol. 41,p. 4036 - 4052
[9]Synlett,1999,p. 1559 - 1562
[10]Organic and Biomolecular Chemistry,2012,vol. 10,p. 2289 - 2299
[11]Synthesis,1990,p. 1145 - 1147
[12]Journal of the Chemical Society. Chemical communications,1987,p. 904 - 905
[13]Journal of Organic Chemistry,1997,vol. 62,p. 261 - 274
[14]Tetrahedron Letters,2004,vol. 45,p. 9277 - 9280
[15]Synlett,2006,p. 881 - 884
[16]Chemistry - A European Journal,2007,vol. 13,p. 5937 - 5943
[17]Tetrahedron,2009,vol. 65,p. 1951 - 1956
[18]Journal of Organometallic Chemistry,2016,vol. 820,p. 120 - 124
[19]Angewandte Chemie - International Edition,2017,vol. 56,p. 15441 - 15445
Angew. Chem.,2017,vol. 129,p. 15643 - 15647,5
[20]Organic Letters,2019,vol. 21,p. 36 - 39
[21]Organic and Biomolecular Chemistry,2019,vol. 17,p. 5916 - 5919
[22]Organic Letters,2019,vol. 21,p. 5912 - 5916
[23]Journal of the American Chemical Society,2001,vol. 123,p. 8864 - 8865
[24]Tetrahedron Letters,2020,vol. 61
[25]Organometallics,2020,vol. 39,p. 2189 - 2196

9
[ 66107-32-2 ]
[ 98-80-6 ]
[ 2920-38-9 ]

Yield	Reaction Conditions	Operation in experiment
21%		Method A 4-Trifluoromethanesulfonylbenzonitrile 21 (126 mg, 0.500 mmol), phenylboronic acid 22 (106.8 mg, 0.6 mmol), (dppf)Ni[P(OPh)3]2 (30.6 mg, 0.0250 mmol), DPPF (13.9 mg, 0.0250 mmol), and potassium phosphate (424 mg, 2.00 mmol) were dissolved in 1,4-dioxane (3 mL) and stirred in a sealed vessel at 100 C under nitrogen for 16 h. The reaction was cooled to RT and water was added (3 mL). The aqueous layer was extracted with dichloromethane (35 mL) and the combined organic layers were washed with water (25 mL) and dried with MgSO4. After filtration, the solvent was removed unde rreduced pressure to give a yellow-brown oil, which was subjected to column chromatography (hexanes/EtOAc 100 : 0 - 97 : 3) to afford a yellow solid, which was then stirred with H2O2 (3mL of a 30% w/w aqueous solution) for 30 min. The mixture was extracted with ethyl acetate (23 mL), dried over MgSO4, and filtered through a plug of silica to afford 4-phenyl benzonitrile 23 as a white solid (18.4 mg, 21 %). The spectral data were in accordance with those reported in the literature.[66] δH (CDCl3, 500 MHz) 7.68 (2H, d, J 8.5, Ar-H), 7.72 (2H, d, J 8.0, Ar-H), 7.59 (2H, d, J 7.5, Ar-H), 7.48 (2H, dd, J 7.5,7, Ar-H), 7.42 (1H, d, J 7.5,7, Ar-H). δC (CDCl3, 125 MHz): 145.7, 139.2, 132.6, 128.7, 127.8, 127.3, 119.0, 110.9.

Reference： [1]Organic Letters,2015,vol. 17,p. 1942 - 1945
[2]Chemistry - A European Journal,2007,vol. 13,p. 5937 - 5943
[3]Tetrahedron Letters,1994,vol. 35,p. 3277 - 3280
[4]Australian Journal of Chemistry,2015,vol. 68,p. 1842 - 1853

10
[ 66107-32-2 ]
[ 109-73-9 ]
[ 4714-65-2 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 1268 - 1273

11
[ 66107-32-2 ]
[ 171364-79-7 ]
[ 58743-77-4 ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 3447 - 3450
[2]Journal of Organic Chemistry,2019,vol. 84,p. 12686 - 12691

12
[ 66107-32-2 ]
[ 171364-81-1 ]
[ 59211-64-2 ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 3447 - 3450

13
[ 66107-32-2 ]
[ 71478-47-2 ]
[ 2920-38-9 ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 4397 - 4400
[2]Journal of Organometallic Chemistry,2001,vol. 624,p. 376 - 379

14
[ 66107-32-2 ]
[ 1591-30-6 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 261 - 274

15
[ 66107-32-2 ]
[ 103-67-3 ]
4-cyano-N-methyl-N-benzylaniline [ No CAS ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 6363 - 6366

16
[ 66107-32-2 ]
[ 3989-14-8 ]
[ 56982-37-7 ]

Reference： [1]Chemistry Letters,1997,p. 1233 - 1234
[2]Journal of Organic Chemistry,2000,vol. 65,p. 1780 - 1787

17
[ 66107-32-2 ]
[ 40231-03-6 ]
4-[2-(2-thienyl)ethynyl]benzonitrile [ No CAS ]

Reference： [1]Chemistry Letters,1997,p. 1233 - 1234
[2]Journal of Organic Chemistry,2000,vol. 65,p. 1780 - 1787

18
[ 66107-32-2 ]
[ 36602-05-8 ]
[ 873-74-5 ]

Reference： [1]Journal of the American Chemical Society,1998,vol. 120,p. 7651 - 7652

19
[ 66107-32-2 ]
[ 762-72-1 ]
4-(1-trimethylsilanylmethyl-vinyl)benzonitrile [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 5076 - 5079

20
[ 201230-82-2 ]
[ 66107-32-2 ]
[ 98-80-6 ]
[ 1503-49-7 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 86502 - 86509
[2]Journal of Organic Chemistry,1998,vol. 63,p. 4726 - 4731

21
[ 66107-32-2 ]
[ 1066-54-2 ]
[ 75867-40-2 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 4036 - 4052
[2]Journal of Organic Chemistry,2001,vol. 66,p. 4165 - 4169

22
[ 109-79-5 ]
[ 66107-32-2 ]
[ 219915-65-8 ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 9606 - 9607
[2]Organic Syntheses,2002,vol. 79,p. 43 - 43

23
[ 109-01-3 ]
[ 66107-32-2 ]
[ 34334-28-6 ]

Reference： [1]Synlett,1999,p. 1559 - 1562

24
[ 1191-99-7 ]
[ 66107-32-2 ]
[ 131516-07-9 ]

Reference： [1]Chemical Communications,1999,p. 1811 - 1812

25
[ 66107-32-2 ]
[ 90-04-0 ]
4-[(2-methoxyphenyl)amino]benzonitrile [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 1158 - 1174

26
[ 66107-32-2 ]
potassim 4-fluorophenyltrifluoroborate [ No CAS ]
[ 10540-31-5 ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 6887 - 6889

27
[ 66107-32-2 ]
potassium (4-methylphenyl)trifluoroborate [ No CAS ]
[ 50670-50-3 ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 6887 - 6889

28
[ 66107-32-2 ]
[ 140-88-5 ]
[ 116460-89-0 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 6130 - 6134

29
[ 998-30-1 ]
[ 66107-32-2 ]
[ 18053-03-7 ]
[ 100-47-0 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 4087 - 4094

30
[ 66107-32-2 ]
potassium (2-phenylethynyl)trifluoroborate [ No CAS ]
[ 29822-79-5 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 7091 - 7093

31
[ 66107-32-2 ]
potassium (5-chloro-1-pentyn-1-yl)trifluoroborate [ No CAS ]
4-(5-chloro-1-pentyn-1-yl)benzonitrile [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 7091 - 7093

32
[ 66107-32-2 ]
potassium (1-hexyn-1-yl)trifluoroborate [ No CAS ]
[ 175203-91-5 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 7091 - 7093

33
[ 66107-32-2 ]
potassium vinyltrifluoroborate [ No CAS ]
[ 3435-51-6 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 7091 - 7093

34
[ 109-01-3 ]
bis(triphenylphosphine)palladium(II) dichloride [ No CAS ]
[ 167858-40-4 ]
[ 66107-32-2 ]
[ 167858-20-0 ]

Yield	Reaction Conditions	Operation in experiment
83%	With copper(I) iodide; triethylamine; triphenylphosphine; In water;	EXAMPLE 7 In a four necked flask equipped with a thermometer and a stirrer, <strong>[66107-32-2]4-cyano-1-trifluoromethanesulfonyloxybenzene</strong> (6.4 g, 0.026 mol), 4-(1-trans-pentenyl)phenylacetylene (3.4 g, 0.02 mol), bis(triphenylphosphine)palladium chloride (0.15 g), cuprous iodide (0.15 g), triphenylphosphine (0.6 g), triethylamine (20 ml) and N-methylpiperazine (30 ml) were charged and refluxed under nitrogen atmosphere for 6 hours. After the completion of the reaction, the reaction mixture was poured in water (100 ml) and extracted with toluene (100 ml). The toluene layer was washed with 3% hydrochloric acid and then water, followed by concentration under reduced pressure to obtain a pale yellow residue. Then, the residue was purified by silica gel column chromatography (eluent: toluene-hexane) to obtain 1-(4-cyanophenyl)-2-[4-(1-trans-pentenyl)phenyl]acetylene (4.5 g). Yield: 83%. Optical anisotropy value Δn of 1-(4-cyanophenyl)-2-[4-(1-trans-pentenyl)phenyl]acetylene: 0.523.

Reference： [1]Patent: US5658489,1997,A

35
[ 66107-32-2 ]
N-butyl-4-aminobenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-butylamine;	EXAMPLE 18 N-Butyl-4-aminobenzonitrile STR19 General procedure B using 62.4 mg (0.248 mmol) of 4-cyanophenyltriflate and 36.8 μl (0.373 mmol) of n-butylamine gave 95% yield of N-butyl-4-aminobenzonitrile after silica gel chromatography using a gradient of 5 to 15% ethyl acetate in hexanes.

Reference： [1]Patent: US5817877,1998,A

36
[ 5570-77-4 ]
[ 66107-32-2 ]
[ 1003194-34-0 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 5529 - 5532

37
[ 591-87-7 ]
[ 66107-32-2 ]
[ 51980-05-3 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 1165 - 1168

38
[ 925430-09-7 ]
[ 66107-32-2 ]
[ 1126-27-8 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 3604 - 3607

39
[ 66107-32-2 ]
[ 603-33-8 ]
[ 92-52-4 ]
[ 2920-38-9 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 5762 - 5772

40
[ 66107-32-2 ]
[ 5142-75-6 ]
[ 613-33-2 ]
[ 50670-50-3 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 5762 - 5772

41
[ 66107-32-2 ]
[ 33397-21-6 ]
[ 2132-80-1 ]
[ 58743-77-4 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 5762 - 5772

42
[ 1590-08-5 ]
[ 66107-32-2 ]
(R)-2-methyl-2-(4-cyanophenyl)-1-tetralone [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 195 - 200

43
[ 17496-14-9 ]
[ 66107-32-2 ]
(R)-4-(2-methyl-1-oxo-2,3-dihydro-1H-inden-2-yl)benzonitrile [ No CAS ]
4-(2-methyl-1-oxo-2,3-dihydro-1H-inden-2-yl)benzonitrile [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 195 - 200

44
[ 5471-63-6 ]
[ 66107-32-2 ]
[ 642493-25-2 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 472 - 480

45
[ 66107-32-2 ]
[ 51934-41-9 ]
[ 89409-89-2 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7380 - 7382

46
[ 1086974-99-3 ]
[ 66107-32-2 ]
[ 1086975-06-5 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 15792 - 15793
[2]Journal of the American Chemical Society,2008,vol. 130,p. 15792 - 15793

47
[ 166328-14-9 ]
[ 66107-32-2 ]
[ 64468-77-5 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 973 - 980

48
[ 66107-32-2 ]
[ 619-72-7 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 12898 - 12899

49
[ 66107-32-2 ]
[ 126747-14-6 ]

Yield	Reaction Conditions	Operation in experiment
70%		General procedure: Triphenylphosphene (0.131 g, 0.5 mmol, 20 mol %), p-iodoanisol (0.585 g, 2.5 mmol), and triethylamine (1.78 mL, 12.5 mmol) were added to a 50 mL round-bottomed flask equipped with a sidearm, condenser, and stir bar. This solution was then degassed by alternating vacuum and argon three times. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol %) was then added under positive argon pressure. After stirring at room temperature for 15 min, diisopropylaminoborane (5 mL, 1 M solution in THF, 5 mmol) was added and the reaction mixture was degassed again by alternating vacuum and argon three times. The reaction solution was then heated to reflux. After 12 h of reflux the reaction was cooled to 0 C and 6 mL of methanol was added through the condenser slowly (Caution: exothermic reaction with evolution of hydrogen). After 15 min of stirring all the solvent was removed under reduced pressure to yield a black solid. This solid was dissolved with sodium hydroxide (3 M, 8 mL) and subsequently washed with hexanes (3×10 mL). The aqueous layer was then cooled to 0 C (ice bath) and acidified to pH ≤1 with concentrated HCl, with the boronic acid usually precipitating out as a white solid. The aqueous fraction was then extracted with diethyl ether (3×10 mL). The organic fractions were combined, dried with magnesium sulfate and filtered. The solvent was then removed under reduced pressure yielding a white solid.

Reference： [1]Tetrahedron,2011,vol. 67,p. 576 - 583

50
[ 363-72-4 ]
[ 66107-32-2 ]
2’,3’,4’,5’,6’-pentafluoro-[1,1’-biphenyl]-4-carbonitrile [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 2289 - 2299

51
[ 74370-93-7 ]
[ 66107-32-2 ]
[ 1275988-03-8 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 1432 - 1435

52
[ 2446-83-5 ]
[ 66107-32-2 ]
[ 1334500-66-1 ]

Yield	Reaction Conditions	Operation in experiment
84%		General procedure: To a stirred solution of DIAD (1.2 mmol) in DMF (2 mL) at 0 C,NaH (0.05 g, 1.2 mmol) was added in portions over 20 min.Then, the aryl O-triflate (1.0 mmol), LiI (134 mg, 1mmol), andCu2O (15 mg, 0.1 mmol) were added to the reaction mixture,which was stirred at 80 C for 8 h under N2. The reaction wascooled and quenched by adding CH2Cl2 (2 mL) and sat. aq NH4Cl(3 mL). The mixture was stirred for an additional 30 min, andtwo layers were separated. The aqueous layer was extractedwith CH2Cl2 (3 × 2 mL), the combined organic layers were driedover MgSO4, filtered, and concentrated in vacuo. The residuewas purified by chromatography (silica gel; hexane-EtOAc, 3:1)to give the product.

Reference： [1]Synlett,2015,vol. 26,p. 942 - 944

53
[ 98437-24-2 ]
[ 66107-32-2 ]
[ 41013-94-9 ]

Reference： [1]RSC Advances,2015,vol. 5,p. 69776 - 69781

54
[ 66107-32-2 ]
[ 5720-07-0 ]
[ 58743-77-4 ]

Reference： [1]RSC Advances,2015,vol. 5,p. 69776 - 69781

55
[ 66107-32-2 ]
[ 4559-70-0 ]
[ 5032-54-2 ]