Organobismuth Compounds as Aryl Radical Precursors via Light-Driven Single-Electron Transfer

Nicholas D. Chiappini, Eric P. Geunes, Ethan T. Bodak, Robert R. Knowles

Research output: Contribution to journalArticlepeer-review

Abstract

A light-driven method for the generation of aryl radicals from triarylbismuth(III) and (V) reagents is described. Aryl radical generation is proposed to occur through the ligand-assisted mesolytic cleavage of an organobismuth(IV) intermediate generated from either oxidation of BiIII or reduction of BiV. This mode of aryl radical generation is demonstrated to be compatible with a range of bimolecular radical arylations, including hydroarylation of electron-deficient olefins and arylation of diboronates, disulfides, sulfonyl cyanides, phosphites, and isocyanides. The intermediacy of an aryl radical is supported by radical trapping and radical clock experiments, and BiIV-aryl mesolysis is supported computationally.

Original languageEnglish (US)
Pages (from-to)2664-2670
Number of pages7
JournalACS Catalysis
Volume14
Issue number4
DOIs
StatePublished - Feb 16 2024

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry

Keywords

  • aryl radical
  • arylbismuth
  • organobismuth
  • photochemical
  • radical generation

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