Metallaphotoredox Difluoromethylation of Aryl Bromides

Vlad Bacauanu, Sébastien Cardinal, Motoshi Yamauchi, Masaru Kondo, David F. Fernández, Richard Remy, David W.C. MacMillan

Research output: Contribution to journalArticle

43 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)12543-12548
Number of pages6
JournalAngewandte Chemie - International Edition
Volume57
Issue number38
DOIs
StatePublished - Sep 17 2018

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • difluoromethylation
  • fluorine
  • heterocycles
  • nickel
  • photoredox catalysis

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  • Cite this

    Bacauanu, V., Cardinal, S., Yamauchi, M., Kondo, M., Fernández, D. F., Remy, R., & MacMillan, D. W. C. (2018). Metallaphotoredox Difluoromethylation of Aryl Bromides. Angewandte Chemie - International Edition, 57(38), 12543-12548. https://doi.org/10.1002/anie.201807629