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Trifluoromethylation of Arylsilanes with [(phen)CuCF3 ].

ABSTRACT: A method for the trifluoromethylation of arylsilanes is reported. The reaction proceeds with [(phen)CuCF3 ] as the CF3 ?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-CF3 bond in active pharmaceutical ingredients which do not undergo this overall transformation by alternative functionalization processes, including a combination of borylation and trifluoromethylation.

SUBMITTER: Morstein J

PROVIDER: S-EPMC4976628 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

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Trifluoromethylation of Arylsilanes with [(phen)CuCF3 ].

Morstein Johannes J Hou Haiyun H Cheng Chen C Hartwig John F JF

Angewandte Chemie (International ed. in English) 20160523 28

A method for the trifluoromethylation of arylsilanes is reported. The reaction proceeds with [(phen)CuCF3 ] as the CF3 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 ...[more]

PMID: 27214849

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