Copper-Catalyzed Trifluoromethylation of Alkyl Bromides

David J.P. Kornfilt, David W.C. Macmillan

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Abstract

Copper oxidative addition into organohalides is a challenging two-electron process. In contrast, formal oxidative addition of copper to C sp2 carbon-bromine bonds can be accomplished by employing latent silyl radicals under photoredox conditions. This novel paradigm for copper oxidative addition has now been applied to a Cu-catalyzed cross-coupling of C sp3-bromides. Specifically, a copper/photoredox dual catalytic system for the coupling of alkyl bromides with trifluoromethyl groups is presented. This operationally simple and robust protocol successfully converts a variety of alkyl, allyl, benzyl, and heterobenzyl bromides into the corresponding alkyl trifluoromethanes. ©

Original languageEnglish (US)
Pages (from-to)6853-6858
Number of pages6
JournalJournal of the American Chemical Society
Volume141
Issue number17
DOIs
StatePublished - May 1 2019

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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