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Single C−F Bond Cleavage of Trifluoromethylarenes with an ortho ‐Silyl Group
Author(s) -
Yoshida Suguru,
Shimomori Ken,
Kim Youngchan,
Hosoya Takamitsu
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201604776
Subject(s) - silylation , carboxylation , chemistry , nucleophile , surface modification , derivatization , cleavage (geology) , bond cleavage , group (periodic table) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , materials science , fracture (geology) , composite material , high performance liquid chromatography
Abstract The transformation of a single C−F bond of trifluoromethylarenes bearing a hydrosilyl group at the ortho position was achieved. The activation of the hydrosilyl group with a trityl cation in the presence of nucleophiles allowed for selective C−F bond functionalization, for example, by allylation, carboxylation, or chlorination. Further derivatization of the resulting fluorosilylarenes afforded various aromatic difluoromethylene compounds.