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Issue 8, 2013
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Catalytic hydrotrifluoromethylation of styrenes and unactivated aliphatic alkenesvia an organic photoredox system

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Abstract

Herein is presented a direct method for the metal-free hydrotrifluoromethylation of alkenes. The method relies on the single electron oxidation of a commercially available sodium trifluoromethanesulfinate salt (CF3SO2Na, Langlois reagent) by N-Me-9-mesityl acridinium as a photoredox catalyst. Methyl thiosalicylate is used as a substoichiometric H-atom donor for aliphatic alkenes, and thiophenol is used as a stoichiometric H-atom donor for styrenyl substrates. The substrate scope for the transformation is broad, including mono-, di- and trisubstituted aliphatic and styrenyl alkenes, with high regioselectivity in nearly all cases examined.

Graphical abstract: Catalytic hydrotrifluoromethylation of styrenes and unactivated aliphatic alkenes via an organic photoredox system

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Article information


Submitted
02 May 2013
Accepted
21 May 2013
First published
21 May 2013

Chem. Sci., 2013,4, 3160-3165
Article type
Edge Article

Catalytic hydrotrifluoromethylation of styrenes and unactivated aliphatic alkenes via an organic photoredox system

D. J. Wilger, N. J. Gesmundo and D. A. Nicewicz, Chem. Sci., 2013, 4, 3160
DOI: 10.1039/C3SC51209F

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