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. 2016 Jul 4;55(28):8054-7.
doi: 10.1002/anie.201601163. Epub 2016 May 23.

Trifluoromethylation of Arylsilanes with [(phen)CuCF3 ]

Johannes Morstein  1 , Haiyun Hou  1 , Chen Cheng  1 , John F Hartwig  2
Affiliations

Trifluoromethylation of Arylsilanes with [(phen)CuCF3 ]

Johannes Morstein et al. Angew Chem Int Ed Engl. .

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.

Keywords: arenes; copper; cross-coupling; fluorine; silanes.

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Figures

Scheme 1
Scheme 1
Common reagents for the trifluoromethylation of prefunctionalized arenes.
Scheme 2
Scheme 2
Copper-mediated trifluoromethylation of arylsilanes.
See this image and copyright information in PMC

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