Issue 9, 2017

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
17 Apr 2017
Accepted
08 Jul 2017
First published
10 Jul 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2017,8, 6375-6379

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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