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Fluorinated Vinylsilanes from the Copper‐Catalyzed Defluorosilylation of Fluoroalkene Feedstocks

2017; Wiley; Volume: 57; Issue: 1 Linguagem: Inglês

10.1002/anie.201710866

1521-3773

Hironobu Sakaguchi, Masato Ohashi, Sensuke Ogoshi,

Inorganic Fluorides and Related Compounds

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.