* 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 [AlH3(triethylamine)] In hexane at 20℃; for 0.166667 h; Inert atmosphere; Schlenk technique
General procedure: Triphenylphosphine oxide or sulfide (1 mmol), dry hexane (1 mL), and Ic (1 mmol) were added to a Schlenk tube under the atmosphere of nitrogen. The reaction was carried out at room temperature for 10 min and monitored by TLC. Upon completion of the process the reaction mixture was filtered by silica gel and washed several times with ethyl acetate. Ethyl acetate was evaporated and the residue purified by flash chromatography on silica gel with pure cyclohexane toafford the desired phosphine. The yield was determined by GC without additional purification.
Reference：
[1] Journal of Organic Chemistry, 2008, vol. 73, # 4, p. 1524 - 1531
[2] Russian Journal of General Chemistry, 2015, vol. 85, # 5, p. 1156 - 1160[3] Zh. Obshch. Khim.,
[4] Advanced Synthesis and Catalysis, 2016, vol. 358, # 1, p. 26 - 29
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Reference：
[1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 18, p. 4069 - 4081
[2] Journal of Organic Chemistry, 1991, vol. 56, # 8, p. 2762 - 2769
[3] Chemische Berichte, 1984, vol. 117, # 9, p. 2791 - 2802
[4] Journal of Fluorine Chemistry, 1980, vol. 15, p. 239 - 244
[5] Chemical Communications, 2016, vol. 52, # 97, p. 14019 - 14022
[6] Organic Letters, 2017, vol. 19, # 19, p. 5434 - 5437
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Yield
Reaction Conditions
Operation in experiment
35%
With hydrogenchloride; n-butyllithium In diethyl ether; hexane; water
PREPARATION OF TRIS(4-TRIFLUOROMETHYLPHENYL)PHOSPHINE (R=4-trifluomethylphenyl) 8 grams of 4-bromobenzotrifluoride were dissolved in 45 milliliters of anhydrous diethylether at 0° C. under a nitrogen atmosphere. 14 milliliters of a 2.5 M solution of n-butyllithium in hexane were then added to the solution via syringe, with stirring, over a 10 minute period. The solution was stirred for 30 minutes at 0° C., and then a solution of 1 milliliter of phosphorous trichloride in 15 milliliters of diethylether was added to the solution dropwise over a 50 minute period. The resulting mixture was warmed to room temperature and stirred for 21/2 hours, then quenched with 50 milliliters of a 5 percent solution of hydrochloric acid. The organic phase of the mixture was washed with 50 milliliters of water, followed by 50 milliliters of aqueous sodium chloride solution. The organic phase was then dried over magnesium sulfate, filtered, and concentrated on a rotavap (rotary evaporator). The resulting product was a red-orange oil, yield 5.31 grams. The product included a triarylphosphine oxide side-product. The side-product was removed by precipitation by the addition of hexane, followed by filtration of the side product. The hexane solvent was removed on a rotavap, and the final product was an orange oil which crystallized upon standing. The triarylphosphine product was purified by recrystallization from methanol. The final yield of the triarylphosphine product was 1.95 grams (yield 35percent).
Reference：
[1] Patent: US5194652, 1993, A,
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Reference：
[1] Synlett, 2006, # 6, p. 954 - 956
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Reference：
[1] J. Gen. Chem. USSR (Engl. Transl.), 1966, vol. 36, p. 1265 - 1269[2] Zhurnal Obshchei Khimii, 1966, vol. 36, # 7, p. 1248 - 1254
With [AlH3(triethylamine)]; In hexane; at 20℃; for 0.166667h;Inert atmosphere; Schlenk technique;
General procedure: Triphenylphosphine oxide or sulfide (1 mmol), dry hexane (1 mL), and Ic (1 mmol) were added to a Schlenk tube under the atmosphere of nitrogen. The reaction was carried out at room temperature for 10 min and monitored by TLC. Upon completion of the process the reaction mixture was filtered by silica gel and washed several times with ethyl acetate. Ethyl acetate was evaporated and the residue purified by flash chromatography on silica gel with pure cyclohexane toafford the desired phosphine. The yield was determined by GC without additional purification.
With hydrogenchloride; n-butyllithium; In diethyl ether; hexane; water;
PREPARATION OF TRIS(4-TRIFLUOROMETHYLPHENYL)PHOSPHINE (R=4-trifluomethylphenyl) 8 grams of 4-bromobenzotrifluoride were dissolved in 45 milliliters of anhydrous diethylether at 0° C. under a nitrogen atmosphere. 14 milliliters of a 2.5 M solution of n-butyllithium in hexane were then added to the solution via syringe, with stirring, over a 10 minute period. The solution was stirred for 30 minutes at 0° C., and then a solution of 1 milliliter of phosphorous trichloride in 15 milliliters of diethylether was added to the solution dropwise over a 50 minute period. The resulting mixture was warmed to room temperature and stirred for 21/2 hours, then quenched with 50 milliliters of a 5 percent solution of hydrochloric acid. The organic phase of the mixture was washed with 50 milliliters of water, followed by 50 milliliters of aqueous sodium chloride solution. The organic phase was then dried over magnesium sulfate, filtered, and concentrated on a rotavap (rotary evaporator). The resulting product was a red-orange oil, yield 5.31 grams. The product included a triarylphosphine oxide side-product. The side-product was removed by precipitation by the addition of hexane, followed by filtration of the side product. The hexane solvent was removed on a rotavap, and the final product was an orange oil which crystallized upon standing. The triarylphosphine product was purified by recrystallization from methanol. The final yield of the triarylphosphine product was 1.95 grams (yield 35percent).
In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere;
General procedure: A 50-mL round-bottom flask was charged with [Ru(p-cymene)Cl2]2 (0.2029 g, 0.331 mmol) and CH2Cl2(20 mL). To the orange solution was added P(C6H4F)3 (0.2199 g, 0.695 mmol), and the mixture was leftto stir for 3 h at room temperature. The volatiles were removed in vacuo to leave a dark red oil, andhexanes were added to precipitate a solid product. The resulting orange solid was collected by vacuumfiltration and dried in vacuo (0.3529 g, 86percent yield).
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