PCET-Enabled Olefin Hydroamidation Reactions with N-Alkyl Amides

Suong T. Nguyen, Qilei Zhu, Robert R. Knowles

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

Olefin aminations are important synthetic technologies for the construction of aliphatic C-N bonds. Here we report a catalytic protocol for olefin hydroamidation that proceeds through transient amidyl radical intermediates that are formed via proton-coupled electron transfer (PCET) activation of the strong N-H bonds in N-alkyl amides by an excited-state iridium photocatalyst and a dialkyl phosphate base. This method exhibits a broad substrate scope, high functional group tolerance, and amenability to use in cascade polycyclization reactions. The feasibility of this PCET protocol in enabling the intermolecular anti-Markovnikov hydroamidation reactions of unactivated olefins is also demonstrated.

Original languageEnglish (US)
Pages (from-to)4502-4507
Number of pages6
JournalACS Catalysis
Volume9
Issue number5
DOIs
StatePublished - May 3 2019

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • amidyl radicals
  • hydroamidation
  • hydrogen atom transfer
  • photoredox catalysis
  • proton-coupled electron transfer

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