Copper-Catalyzed Trifluoromethylation of Alkyl Bromides

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

Research output: Contribution to journalArticle

8 Citations (Scopus)

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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Bromides
Copper
Bromine
Carbon
Electrons

All Science Journal Classification (ASJC) codes

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

Cite this

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Copper-Catalyzed Trifluoromethylation of Alkyl Bromides. / Kornfilt, David J.P.; MacMillan, David W.C.

In: Journal of the American Chemical Society, Vol. 141, No. 17, 01.05.2019, p. 6853-6858.

Research output: Contribution to journalArticle

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