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Issue 8, 2013
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Catalytic hydrotrifluoromethylation of styrenes and unactivated aliphatic alkenes via 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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Publication details

The article was received on 02 May 2013, accepted on 21 May 2013 and first published on 21 May 2013


Article type: Edge Article
DOI: 10.1039/C3SC51209F
Citation: Chem. Sci., 2013,4, 3160-3165
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    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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