Direct β-alkylation of aldehydes via photoredox organocatalysis

Jack A. Terrett, Michael D. Clift, David W.C. MaCmillan

Research output: Contribution to journalArticle

120 Scopus citations

Abstract

Direct β-alkylation of saturated aldehydes has been accomplished by synergistically combining photoredox catalysis and organocatalysis. Photon-induced enamine oxidation provides an activated β-enaminyl radical intermediate, which readily combines with a wide range of Michael acceptors to produce β-alkyl aldehydes in a highly efficient manner. Furthermore, this redox-neutral, atom-economical C-H functionalization protocol can be achieved both inter-and intramolecularly. Mechanistic studies by various spectroscopic methods suggest that a reductive quenching pathway is operable.

Original languageEnglish (US)
Pages (from-to)6858-6861
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number19
DOIs
StatePublished - May 14 2014

All Science Journal Classification (ASJC) codes

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

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