Fluorinated Vinylsilanes from the Copper-Catalyzed Defluorosilylation of Fluoroalkene Feedstocks

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 beta-fluorine elimination, which generates a Cu-F species. The beta-fluorine elimination is facilitated by Lewis acidic F-Bpin, which is generated insitu during the defluorosilylation.