Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
4 years ago

Fluorinated Vinylsilanes from the Copper-Catalyzed Defluorosilylation of Fluoroalkene Feedstocks

Sensuke Ogoshi, Masato Ohashi, Hironobu Sakaguchi
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: i) the 1,2-addition of a silylcopper intermediate to the polyfluoroalkene, and ii) a subsequent selective β-fluorine elimination, which generates a Cu-F species. The β-fluorine elimination is facilitated by the Lewis acidic F-Bpin, which is generated in situ during the defluorosilylation.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201710866

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