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Issue 9, 2017
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Metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis

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Abstract

Regioselective amino-difluoromethylation of aromatic alkenes via C(sp3)–CF2H and C(sp3)–N bond formation with the C[double bond, length as m-dash]C moiety has been achieved in a single operation by visible-light photoredox catalysis. The combination of a shelf-stable and easy-to-handle sulfonium salt, S-difluoromethyl-S-di(p-xylyl)sulfonium tetrafluoroborate, and perylene catalysis is the key to the successful transformation. Furthermore, this noble metal-free protocol allows for the photocatalytic trifluoromethylation of alkenes.

Graphical abstract: Metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis

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Publication details

The article was received on 17 Apr 2017, accepted on 08 Jul 2017 and first published on 10 Jul 2017


Article type: Edge Article
DOI: 10.1039/C7SC01703K
Citation: Chem. Sci., 2017,8, 6375-6379
  • Open access: Creative Commons BY-NC license
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    Metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis

    N. Noto, T. Koike and M. Akita, Chem. Sci., 2017, 8, 6375
    DOI: 10.1039/C7SC01703K

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