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Fluorinated Vinylsilanes from the Copper‐Catalyzed Defluorosilylation of Fluoroalkene Feedstocks
Author(s) -
Sakaguchi Hironobu,
Ohashi Masato,
Ogoshi Sensuke
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201710866
Subject(s) - copper , tetrafluoroethylene , catalysis , chemistry , fluorine , stoichiometry , polymer chemistry , lewis acids and bases , organic chemistry , combinatorial chemistry , copolymer , polymer
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.