title: Copper-catalyzed oxidative trifluoromethylation of terminal alkynes and aryl boronic acids using (trifluoromethyl)trimethylsilane.
abstract: Trifluoromethylated acetylenes and arenes are widely applicable in the synthesis of pharmaceuticals and agrochemicals. In 2010, our group has reported the copper-mediated oxidative trifluomethylation of terminal alkynes and aryl boronic acids. This method allows a wide range of functional group tolerant trifluoromethylated acetylenes and arenes to be easily prepared. After the preliminary mechanistic studies of the oxidative trifluoromethylation of terminal alkyne, an efficient copper-catalyzed oxidative trifluoromethylation of terminal alkynes and aryl boronic acids has been developed. The catalytic protocol is successfully achieved by adding both the substrate and a portion of CF(3)TMS slowly using a syringe pump to the reaction mixture.
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
authors.forename: Xueliang
authors.initials: X
authors.lastname: Jiang
authors.forename: Lingling
authors.initials: L
authors.lastname: Chu
authors.forename: Feng-Ling
authors.initials: FL
authors.lastname: Qing
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D008745:Methylation; D010084:Oxidation-Reduction; D012821:Silanes / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001897:Boronic Acids; D006845:Hydrocarbons, Fluorinated; D012821:Silanes; D003300:Copper; C509472:trimethyl(trifluoromethyl)silane