Benzenamine, 3-(3,3,3-trifluoro-1-propyn-1-yl)- synthesis

Yield: 94%

Reaction Conditions:

with copper(l) iodide;1,10-Phenanthroline;potassium hydrogencarbonate in dichloromethane at 20; for 18 h;Inert atmosphere;

Steps:

General procedure for the Copper-Catalyzed Trifluoromethylation of Terminal Alkynes Using an Electrophilic Trifluoromethylating Reagent
General procedure: In a glovebox, CuI (0.04 mmol), Phen(0.08 mmol), base (0.40 mmol) and electrophilic trifluoromethylating reagent (0.30 mmol) were added to a Schlenk tube that was equipped with a stirring bar. Freshly distilled solvent (1.4 mL) was added into this tube. Terminal alkynes (0.20 mmol) in the same solvent (1.6 mL) was added into a small vial. Both the tube and the vial were capped with a septum and taken out. The solution of alkyne was added to the tube over 6 h by using a syringe pump under Ar atmosphere (1 atm). After addition, the reaction mixture was kept for another 18 h at room temperature. Aqueous phase was extracted with CH₂Cl₂ and the combined organic extracts were dried over anhydrous Na₂SO₄, and concentrated in vacuo. The product was purified by flash chromatography on silica gel with petroether. NMR yield was determined by ¹⁹F NMR using trifluorobenzene as an internal standard before working up the reaction.

References:

Weng, Zhiqiang;Li, Huaifeng;He, Weiming;Yao, Liang-Feng;Tan, Jianwei;Chen, Jinfa;Yuan, Yaofeng;Huang, Kuo-Wei [Tetrahedron,2012,vol. 68,# 11,p. 2527 - 2531] Location in patent:supporting information; experimental part