Rhodium-Catalyzed Enantioselective Radical Addition of CX4 Reagents to Olefins

Bo Chen, Cheng Fang, Peng Liu, Joseph M. Ready

Research output: Contribution to journalArticle

26 Scopus citations

Abstract

We describe the synthetically useful enantioselective addition of Br−CX3 (X=Cl or Br) to terminal olefins to introduce a trihalomethyl group and generate optically active secondary bromides. Computational and experimental evidence supports an asymmetric atom-transfer radical addition (ATRA) mechanism in which the stereodetermining step involves outer-sphere bromine abstraction from a [(bisphosphine)RhIIBrCl] complex by a benzylic radical intermediate. This mechanism appears unprecedented in asymmetric catalysis.

Original languageEnglish (US)
Pages (from-to)8780-8784
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number30
DOIs
StatePublished - Jul 17 2017

Keywords

  • alkenes
  • asymmetric catalysis
  • enantioselectivity
  • radical reactions
  • rhodium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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