Synthesis of 3-acylindoles by visible-light induced intramolecular oxidative cyclization of o-alkynylated N,N-dialkylamines

Org Lett. 2014 Jun 20;16(12):3264-7. doi: 10.1021/ol501276j. Epub 2014 Jun 4.

Abstract

A visible-light photoredox synthesis of 3-acylindoles through intramolecular oxidative cyclization of o-alkynylated N,N-dialkylamines is developed. The reaction proceeds effectively under mild reaction conditions using air as the oxidant, and only water is generated as a side product. A plausible mechanism involving the addition of α-amino alkyl radicals to alkynes, followed by C-O bond formation, is proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Amines / chemistry*
  • Catalysis
  • Cyclization
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Light
  • Molecular Structure
  • Oxidation-Reduction
  • Water / chemistry

Substances

  • Alkynes
  • Amines
  • Indoles
  • Water