Intramolecular 1,5-H transfer reaction of aryl iodides through visible-light photoredox catalysis: a concise method for the synthesis of natural product scaffolds

Chem Commun (Camb). 2016 May 11;52(38):6455-8. doi: 10.1039/c6cc02007k. Epub 2016 Apr 21.

Abstract

The intramolecular 1,5-H transfer reaction of the aryl radicals generated from unactivated aryl iodides by photocatalysis is described. The features of this transformation are operational simplicity, excellent yields, mild reaction conditions, and good functional group tolerance. With this approach, a more concise formal synthesis of (±)-coerulescine and (±)-physovenine is accomplished.

MeSH terms

  • Aniline Compounds / chemical synthesis*
  • Aniline Compounds / chemistry
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Catalysis
  • Hydrocarbons, Iodinated / chemistry*
  • Light*
  • Molecular Structure
  • Oxidation-Reduction
  • Photochemical Processes
  • Physostigmine / analogs & derivatives*
  • Physostigmine / chemical synthesis
  • Physostigmine / chemistry

Substances

  • Aniline Compounds
  • Biological Products
  • Hydrocarbons, Iodinated
  • coerulescine
  • physovenine
  • Physostigmine