* 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.
With (1,3-bis(2,6-di-iso-propylphenyl)-4,5-dihydroimidazol-2-ylidene) copper chloride; tris-tert-butylphosphinimide, lithium salt In benzene at 20℃; for 13 h; Glovebox; Inert atmosphere
General procedure: In an N2 charged glove box with oxygen and water levels ≤0.1 ppm, to an oven-dried screwed vial were added SIPrCuCl (c8) (4.9 mg, 5 molpercent, 0.01 mmol), tri(t-Butyl)phosphoranimide (1b) (2.2 mg, 5 molpercent, 0.01 mmol), Pinacolborane (1c) (28 mg, 0.22 mmol, 1.1 eq.), terminal alkyne (1) (0.2 mmol, 1 eq.) and benzene (2 mL, 0.1 M). The formed reaction mixture was kept stirring for 13-15 hours in glove box. Then the dark brown reaction mixture was taken out from glove box the solvent was removed by rotary evaporator. The solvent mixture (Hexane:Ethyl acetate) was added into the reaction residue as eluent then kept stirring for about 30 mins under room temperature until the precipitate was formed. The mixture was further filtered through a short pad of silica gel to get colorless filtrate. Organic solvents were removed under reduced pressure and desired product was obtained after dryness under vacuum without further purification.
Reference：
[1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 19, p. 3649 - 3654
[2] Organic Letters, 2017, vol. 19, # 16, p. 4323 - 4326
[3] Tetrahedron Letters, 2017, vol. 58, # 15, p. 1523 - 1527
[4] Chemistry - An Asian Journal, 2013, vol. 8, # 1, p. 50 - 54
[5] Chemistry Letters, 2013, vol. 42, # 10, p. 1128 - 1130
[6] Chemical Communications, 2016, vol. 52, # 72, p. 10830 - 10833
2
[ 3792-88-9 ]
[ 73183-34-3 ]
[ 1242770-50-8 ]
Yield
Reaction Conditions
Operation in experiment
68%
With copper(l) iodide; lithium methanolate; bis[2-(diphenylphosphino)phenyl] ether In dimethyl sulfoxide at 50℃; for 16 h;
General procedure: Phenylpropiolic acid (439 mg, 3.0 mmol), B2pin2 (763 mg, 3.0 mmol), lithium methoxide (23 mg, 0.6 mmol), copper iodide (57 mg, 0.3 mmol), and Dpe-Phos (324 mg, 0.6 mmol) were added to a vial containing DMSO (5 mL). The suspension was stirred for 16 h at 50 °C. The reaction was monitored by TLC, and after the completion of the reaction, the reaction mass was cooled to 25–28 °C and quenched into a mixture of 50 mL of water and 50 mL of ethyl acetate. The ethyl acetate layer was washed with water (2 × 25 mL), brine (2 × 25 mL), and then dried over Na2SO4. Evaporation of the solvent under reduced pressure provided the crude product, which was purified by column chromatography (hexane:EtOAc = 9.5:0.5).
57%
With copper(II) trifluoroacetate; sodium carbonate In 1,4-dioxane at 80℃; for 18 h; Inert atmosphere
General procedure: A Schlenk tube with a magnetic stirring bar was charged with 3-phenylpropiolic acid (1a, 68 mg, 0.5 mmol), bis(pinacolato)diboron (2a, 152 mg, 0.6 mmol), Cu(TFA)2 (29 mg, 10 molpercent), Na2CO3 (127 mg, 1.2 mmol), and 1,4-dioxane (2 mL) under N2. The reaction mixture was stirred at 80 °C for 18 h (monitored by TLC and GC). Upon completion of the reaction, the reaction mixture was then cooled to ambient temperature, diluted with ethyl acetate (20 mL), filtered through a plug of silica gel, and washed with ethyl acetate (20 mL). The organic layer was washed with saturated brine (20 mL×2) and dried over anhydrous Na2SO4. The solvents were removed via rotary evaporator and the residue was purified by flash chromatography (silica gel, ethyl acetate: petroleum ether=1:30) to give 89.7 mg of desired product 3a in 78 percent yield as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.48–7.50 (m, 2H), 7.41 (d, 1H, J=18.5Hz), 7.29–7.32 (m, 3H), 6.18 (d, 1H, J=18.4Hz), 1.32 (s, 12H). 13C NMR (100 MHz, CDCl3): δ 148.5, 136.4, 127.9, 127.5, 126.0, 82.3, 23.8
Reference：
[1] Bulletin of the Korean Chemical Society, 2016, vol. 37, # 4, p. 463 - 468
[2] Chinese Chemical Letters, 2016, vol. 27, # 4, p. 571 - 574
3
[ 705-31-7 ]
[ 73183-34-3 ]
[ 1242770-50-8 ]
Reference：
[1] Chemistry - An Asian Journal, 2017, vol. 12, # 17, p. 2318 - 2322
[2] Journal of the American Chemical Society, 2011, vol. 133, # 20, p. 7859 - 7871
4
[ 402-43-7 ]
[ 75927-49-0 ]
[ 1242770-50-8 ]
Reference：
[1] New Journal of Chemistry, 2017, vol. 41, # 8, p. 3172 - 3176
5
[ 705-31-7 ]
[ 73183-34-3 ]
[ 1242770-50-8 ]
Reference：
[1] Journal of the American Chemical Society, 2011, vol. 133, # 20, p. 7859 - 7871
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 36, p. 10821 - 10825[3] Angew. Chem., 2017, vol. 129, # 36, p. 10961 - 10965,5
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