Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids

Lingling Chu, Jeffrey M. Lipshultz, David W.C. Macmillan

Research output: Contribution to journalArticle

188 Scopus citations

Abstract

The direct decarboxylative arylation of α-oxo acids has been achieved by synergistic visible-light-mediated photoredox and nickel catalysis. This method offers rapid entry to aryl and alkyl ketone architectures from simple α-oxo acid precursors via an acyl radical intermediate. Significant substrate scope is observed with respect to both the oxo acid and arene coupling partners. This mild decarboxylative arylation can also be utilized to efficiently access medicinal agents, as demonstrated by the rapid synthesis of fenofibrate. The direct decarboxylative arylation of α-oxo acids has been achieved by synergistic visible-light-mediated photoredox and nickel catalysis. This method offers rapid entry to aryl and alkyl ketone architectures from simple α-oxo acid precursors via an acyl radical intermediate. Significant substrate scope is observed with respect to both the oxo acid and arene coupling partners.

Original languageEnglish (US)
Pages (from-to)7929-7933
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number27
DOIs
StatePublished - Jun 1 2015

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • arylation
  • decarboxylation
  • nickel catalysis
  • photoredox catalysis
  • α-oxo acids

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