Selective Radical-Radical Cross-Couplings: Design of a Formal β-Mannich Reaction

Jenna L. Jeffrey, Filip R. Petronijević, David W.C. Macmillan

Research output: Contribution to journalArticle

133 Scopus citations

Abstract

A direct β-coupling of cyclic ketones with imines has been accomplished via the synergistic combination of photoredox catalysis and organocatalysis. Transient β-enaminyl radicals derived from ketones via enamine and oxidative photoredox catalysis readily combine with persistent α-amino radicals in a highly selective hetero radical-radical coupling. This novel pathway to γ-aminoketones is predicated upon the use of DABCO as both a base and an electron transfer agent. This protocol also formally allows for the direct synthesis of β-Mannich products via a chemoselective three-component coupling of aryl aldehydes, amines, and ketones.

Original languageEnglish (US)
Pages (from-to)8404-8407
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number26
DOIs
StatePublished - Jul 8 2015

All Science Journal Classification (ASJC) codes

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

Fingerprint Dive into the research topics of 'Selective Radical-Radical Cross-Couplings: Design of a Formal β-Mannich Reaction'. Together they form a unique fingerprint.

  • Cite this