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Issue 53, 2019
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Metal-free defluorinative arylation of trifluoromethyl alkenes via photoredox catalysis

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Abstract

Literature methods to access gem-difluoroalkenes are largely limited to harsh, organometallic-based methods, and known photoredox-mediated processes are not amenable to aryl radical addition to trifluoromethyl alkenes. A metal-free, functional group-tolerant method for the preparation of benzylic gem-difluoroalkenes is described. Halogen atom abstraction from (hetero)aryl halides generates aryl radicals that undergo a defluorinative arylation of α-trifluoromethyl alkenes, tolerating electronically disparate aryl radicals and α-trifluoromethyl alkenes.

Graphical abstract: Metal-free defluorinative arylation of trifluoromethyl alkenes via photoredox catalysis

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Supplementary files

Article information


Submitted
03 Jun 2019
Accepted
07 Jun 2019
First published
07 Jun 2019

Chem. Commun., 2019,55, 7599-7602
Article type
Communication

Metal-free defluorinative arylation of trifluoromethyl alkenes via photoredox catalysis

R. J. Wiles, J. P. Phelan and G. A. Molander, Chem. Commun., 2019, 55, 7599
DOI: 10.1039/C9CC04265B

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