Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 38, Pages 12543-12548Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201807629
Keywords
difluoromethylation; fluorine; heterocycles; nickel; photoredox catalysis
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Funding
- NIHGMS [R01 GM103558-05]
- Fonds de Recherche du Quebec - Nature et Technologies (FRQNT) [198859]
- Daiichi Sankyo Co., Ltd.
- MINECO [BES-2014-068776, EEBB-I-17-11925]
- Swiss National Science Foundation [P2FRP2-178091]
- Swiss National Science Foundation (SNF) [P2FRP2_178091] Funding Source: Swiss National Science Foundation (SNF)
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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 show cased in the late-stage functionalization of several drug analogues.
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