Practical Method for the Cu-Mediated Trifluoromethylation of Arylboronic Acids with CF₃ Radicals Derived from NaSO₂CF₃ and tert-Butyl Hydroperoxide (TBHP)

Yingda Ye, Stefan A. Künzi and Melanie S. Sanford*

*Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States, Email: mssanforumich.edu

Y. Ye, S. A. Künzi, M. S. Sanford, Org. Lett., 2012, 14, 4979-7981.

DOI: 10.1021/ol3022726

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Abstract

A mild and practical protocol for the copper-mediated trifluoromethylation of aryl and heteroaryl boronic acids using NaSO₂CF₃ (Langlois' reagent) and TBHP proceeds at room temperature under ambient conditions. The products can be readily purified by extraction or column chromatography.

see article for more examples

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Merging Visible-Light Photocatalysis and Transition-Metal Catalysis in the Copper-Catalyzed Trifluoromethylation of Boronic Acids with CF₃I

Y. Ye, M. S. Sanford, J. Am. Chem. Soc., 2012, 134, 9034-9037.

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Key Words

trifluoromethylation, TBHP

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ID: J54-Y2012-3140