Nickel(IV)-Catalyzed C–H Trifluoromethylation of (Hetero)arenes

This Article describes the development of a stable NiIV complex that mediates C­(sp2)–H trifluoro­methylation reactions. This reactivity is first demonstrated stoichiometrically and then successfully translated to a NiIV-catalyzed C–H trifluoro­methylation of electron-rich arene and heteroarene subs...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2019-08, Vol.141 (32), p.12872-12879
Main Authors: Meucci, Elizabeth A, Nguyen, Shay N, Camasso, Nicole M, Chong, Eugene, Ariafard, Alireza, Canty, Allan J, Sanford, Melanie S
Format: Article
Language:English
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Summary:This Article describes the development of a stable NiIV complex that mediates C­(sp2)–H trifluoro­methylation reactions. This reactivity is first demonstrated stoichiometrically and then successfully translated to a NiIV-catalyzed C–H trifluoro­methylation of electron-rich arene and heteroarene substrates. Both experimental and computational mechanistic studies support a radical chain pathway involving NiIV, NiIII, and NiII intermediates.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b06383