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Trifluoromethylation of Arylsilanes with [(phen)CuCF 3 ]
Author(s) -
Morstein Johannes,
Hou Haiyun,
Cheng Chen,
Hartwig John F.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201601163
Subject(s) - trifluoromethylation , borylation , chemistry , silylation , compatibility (geochemistry) , aryl , combinatorial chemistry , reagent , catalysis , organic chemistry , trifluoromethyl , chemical engineering , alkyl , engineering
A method for the trifluoromethylation of arylsilanes is reported. The reaction proceeds with [(phen)CuCF 3 ] as the CF 3 source under mild, oxidative conditions with high functional‐group compatibility. This transformation complements prior trifluoromethylation of arenes in several ways. Most important, this method converts arylsilanes formed by the silylation of aryl C−H bonds to trifluoromethylarenes, thereby allowing the conversion of arenes to trifluoromethylarenes. The unique capabilities of the reported method are demonstrated by the conversion of a C−H bond into a C−CF 3 bond in active pharmaceutical ingredients which do not undergo this overall transformation by alternative functionalization processes, including a combination of borylation and trifluoromethylation.