Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 8, Pages 2934-2938Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201508622
Keywords
C-H functionalization; fluorine; gold catalysis; photocatalysis
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The first gold-catalyzed photoredox C(sp(2))-H difluoroalkylation and perfluoroalkylation of hydrazones with readily available R-F-Br reagents is reported. The resulting gem-difluoromethylated and perfluoroalkylated hydrazones are highly functionalized, versatile molecules. A mild reduction of the coupling products can efficiently produce gem-difluoromethylated beta-amino phosphonic acids and beta-amino acid derivatives. In mechanistic studies, a difluoroalkyl radical intermediate was detected by an EPR spin-trapping experiment, indicating that a gold-catalyzed radical pathway is operating.
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