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Metallaphotoredox Difluoromethylation of Aryl Bromides
Authors:Vlad Bacauanu  Sébastien Cardinal  Motoshi Yamauchi  Masaru Kondo  David F. Fernández  Richard Remy  Prof. Dr. David W. C. MacMillan
Affiliation:1. http://www.princeton.edu/chemistry/macmillan/ 0000-0003-3089-0692 Merck Center for Catalysis at Princeton University, Princeton, NJ, USA;2. Merck Center for Catalysis at Princeton University, Princeton, NJ, USA
Abstract: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.
Keywords:difluoromethylation  fluorine  heterocycles  nickel  photoredox catalysis
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