Reductive N-Heterocyclic Carbene Catalysis via Hydride Transfer: Generating Homoenolates from Unsaturated Esters

Mingyi Pan, Qingyun Wang, Pengcheng Zheng*, Yonggui Robin Chi*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

In N-heterocyclic carbene (NHC) catalysis, the reduction of NHC-bound acyl azolium species is achieved with progress limited to the generation of ketyl radical intermediates. Here, we report a novel NHC-catalyzed reductive mode for acyl azolium intermediates, which accept a hydride to generate the Breslow intermediate. Then, the reaction of the Breslow intermediate with chalcone results in the formation of cyclopentene, demonstrating a classic umpolung transformation. We expect that this catalytic reductive mode will open new avenues for synthetic transformations.

Original languageEnglish
JournalOrganic Letters
DOIs
Publication statusAccepted/In press - 2025
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2025 American Chemical Society.

ASJC Scopus Subject Areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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