Fluorinated Vinylsilanes from the Copper-Catalyzed Defluorosilylation of Fluoroalkene Feedstocks

Abstract

Herein, a copper-catalyzed C-F bond defluorosilylation reaction of tetrafluoroethylene and other polyfluoroalkenes is described. Mechanistic studies, based on a series of stoichiometric reactions with copper complexes, revealed that the key steps of this defluorosilylation reaction are 1) the 1,2-addition of a silylcopper intermediate to the polyfluoroalkene and 2) a subsequent selective β-fluorine elimination, which generates a Cu-F species. The β-fluorine elimination is facilitated by Lewis acidic F-Bpin, which is generated in situ during the defluorosilylation.

Keywords: copper; organofluorine compounds; organosilicon compounds; silylcupration; β-fluorine elimination.