Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids

Anna V. Davies, Keegan P. Fitzpatrick, Rick C. Betori, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

As a key element in the construction of complex organic scaffolds, the formation of C−C bonds remains a challenge in the field of synthetic organic chemistry. Recent advancements in single-electron chemistry have enabled new methods for the formation of various C−C bonds. Disclosed herein is the development of a novel single-electron reduction of acyl azoliums for the formation of ketones from carboxylic acids. Facile construction of the acyl azolium in situ followed by a radical–radical coupling was made possible merging N-heterocyclic carbene (NHC) and photoredox catalysis. The utility of this protocol in synthesis was showcased in the late-stage functionalization of a variety of pharmaceutical compounds. Preliminary investigations using chiral NHCs demonstrate that enantioselectivity can be achieved, showcasing the advantages of this protocol over alternative methodologies.

Original languageEnglish (US)
Pages (from-to)9143-9148
Number of pages6
JournalAngewandte Chemie - International Edition
Volume59
Issue number23
DOIs
StatePublished - Jun 2 2020

Keywords

  • N-heterocyclic carbenes
  • ketones
  • photochemistry
  • radicals
  • reaction mechanisms

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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