Photocatalytic acyl azolium-promoted alkoxycarbonylation of trifluoroborates

Joshua L. Zhu, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Despite recent advancements in the selective generation and coupling of organic radical species, the alkoxycarbonyl radical remains underexplored relative to other carbon-containing radical species. Drawing inspiration from new strategies for generating acyl radical equivalents utilizing dual N-heterocyclic carbene catalysis and photocatalysis, we have prepared dimethylimidazolium esters that can function as an alkoxycarbonyl radical surrogate under photocatalytic conditions. We demonstrate the synthetic utility of these azolium-based partners through the preparation of esters arising from the coupling of this radical surrogate with an oxidatively generated alkyl radical.

Original languageEnglish (US)
Article number132288
JournalTetrahedron
Volume92
DOIs
StatePublished - Jul 16 2021

Keywords

  • Alkoxycarbonyl radical
  • Esterification
  • N-Heterocyclic carbene
  • Photocatalysis
  • Radical-radical coupling

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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