Direct β-functionalization of cyclic ketones with aryl ketones via the merger of photoredox and organocatalysis

Filip R. Petronijević, Manuel Nappi, David W.C. MacMillan

Research output: Contribution to journalArticle

131 Scopus citations

Abstract

The direct β-coupling of cyclic ketones with aryl ketones has been achieved via the synergistic combination of photoredox catalysis and organocatalysis. Diaryl oxymethyl or aryl-alkyl oxymethyl radicals, transiently generated via single-electron reduction of ketone precursors, readily merge with β-enaminyl radical species, generated by photon-induced enamine oxidation, to produce γ-hydroxyketone adducts. Experimental evidence indicates that two discrete reaction pathways can be operable in this process depending upon the nature of the ketyl radical precursor and the photocatalyst.

Original languageEnglish (US)
Pages (from-to)18323-18326
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number49
DOIs
StatePublished - Dec 11 2013

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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