Direct Acylation of C(sp3)-H Bonds Enabled by Nickel and Photoredox Catalysis

Candice L. Joe, Abigail G. Doyle

Research output: Contribution to journalArticle

109 Scopus citations

Abstract

Using nickel and photoredox catalysis, the direct functionalization of C(sp3)-H bonds of N-aryl amines by acyl electrophiles is described. The method affords a diverse range of α-amino ketones at room temperature and is amenable to late-stage coupling of complex and biologically relevant groups. C(sp3)-H activation occurs by photoredox-mediated oxidation to generate α-amino radicals which are intercepted by nickel in catalytic C(sp3)-C coupling. The merger of these two modes of catalysis leverages nickel's unique properties in alkyl cross-coupling while avoiding limitations commonly associated with transition-metal-mediated C(sp3)-H activation, including requirements for chelating directing groups and high reaction temperatures. Teamwork: The direct functionalization of C(sp3)-H bonds of N-aryl amines by acyl electrophiles is achieved, thus affording a diverse range of α-amino ketones at room temperature. C(sp3)-H activation occurs by photoredox-mediated oxidation to generate α-amino radicals which are intercepted by nickel in catalytic C(sp3)-C coupling.

Original languageEnglish (US)
Pages (from-to)4040-4043
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number12
DOIs
StatePublished - Mar 14 2016

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • C-H activation
  • acylation
  • cross-coupling
  • nickel
  • photochemistry

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