Combined Photoredox and Carbene Catalysis for the Synthesis of γ-Aryloxy Ketones

Pengzhi Wang, Keegan P. Fitzpatrick, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

N-heterocyclic carbenes (NHCs) have emerged as catalysts for the construction of C−C bonds in the synthesis of substituted ketones under single-electron processes. Despite these recent reports, there still remains a need to increase the utility and practicality of these reactions by exploring new radical coupling partners. Herein, we report the synthesis of γ-aryloxyketones via combined NHC/photoredox catalysis. In this reaction, an α-aryloxymethyl radical is generated via oxidation of an aryloxymethyl potassium trifluoroborate salt, which is then added into styrene derivatives to provide a stabilized benzylic radical. Subsequent radical-radical coupling reaction with an azolium radical affords the γ-aryloxy ketone products. (Figure presented.).

Original languageEnglish (US)
Pages (from-to)518-524
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume364
Issue number3
DOIs
StatePublished - Feb 1 2022

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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