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Metallaphotoredox Difluoromethylation of Aryl Bromides
Author(s) -
Bacauanu Vlad,
Cardinal Sébastien,
Yamauchi Motoshi,
Kondo Masaru,
Fernández David F.,
Remy Richard,
MacMillan David W. C.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201807629
Subject(s) - aryl , electrophile , chemistry , silylation , halogen , combinatorial chemistry , catalysis , alkyl , halide , aryl radical , photoredox catalysis , organic chemistry , photocatalysis
Herein, we report a convenient and broadly applicable strategy for the difluoromethylation of aryl bromides by metallaphotoredox catalysis. Bromodifluoromethane, a simple and commercially available alkyl halide, is harnessed as an effective source of difluoromethyl radical by silyl‐radical‐mediated halogen abstraction. The merger of this fluoroalkyl electrophile activation pathway with a dual nickel/photoredox catalytic platform enables the difluoromethylation of a diverse array of aryl and heteroaryl bromides under mild conditions. The utility of this procedure is showcased in the late‐stage functionalization of several drug analogues.