Light-Driven Carbene Catalysis for the Synthesis of Aliphatic and α-Amino Ketones

Anna V. Bay, Keegan P. Fitzpatrick, Gisela A. González-Montiel, Abdikani Omar Farah, Paul Ha Yeon Cheong, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Single-electron N-heterocyclic carbene (NHC) catalysis has gained attention recently for the synthesis of C−C bonds. Guided by density functional theory and mechanistic analyses, we report the light-driven synthesis of aliphatic and α-amino ketones using single-electron NHC operators. Computational and experimental results reveal that the reactivity of the key radical intermediate is substrate-dependent and can be modulated through steric and electronic parameters of the NHC. Catalyst potential is harnessed in the visible-light driven generation of an acyl azolium radical species that undergoes selective coupling with various radical partners to afford diverse ketone products. This methodology is showcased in the direct late-stage functionalization of amino acids and pharmaceutical compounds, highlighting the utility of single-electron NHC operators.

Original languageEnglish (US)
Pages (from-to)17925-17931
Number of pages7
JournalAngewandte Chemie - International Edition
Volume60
Issue number33
DOIs
StatePublished - Aug 9 2021

Keywords

  • carbene
  • catalysis
  • density functional theory
  • late-stage functionalization
  • photochemistry

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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