Metallaphotoredox Perfluoroalkylation of Organobromides

Xiangbo Zhao, David W.C. MacMillan

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Ruppert-Prakash type reagents (TMSCF3, TMSC2F5, and TMSC3F7) are readily available, air-stable, and easy-to-handle fluoroalkyl sources. Herein, we describe a mild, copper-catalyzed cross-coupling of these fluoroalkyl nucleophiles with aryl and alkyl bromides to produce a diverse array of trifluoromethyl, pentafluoroethyl, and heptafluoropropyl adducts. This light-mediated transformation proceeds via a silyl-radical-mediated halogen atom abstraction pathway, which enables perfluoroalkylation of a broad range of organobromides of variable steric and electronic demand. The utility of the method is demonstrated through the late-stage functionalization of several drug analogues.

Original languageEnglish (US)
Pages (from-to)19480-19486
Number of pages7
JournalJournal of the American Chemical Society
Volume142
Issue number46
DOIs
StatePublished - Nov 18 2020

All Science Journal Classification (ASJC) codes

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

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