A Mild Cu(I)-Catalyzed Oxidative Aromatization of Indolines to Indoles

J Org Chem. 2016 Oct 21;81(20):10009-10015. doi: 10.1021/acs.joc.6b01854. Epub 2016 Oct 12.

Abstract

A novel method for the oxidation of indolines to indoles is described. The method uses a Cu(I) catalyst and an organic percarbonate as the stoichiometric oxidant. The procedure was successfully applied at 0.5 kg scale in the production of a key intermediate in the synthesis of Elbasvir, which is a novel therapy for the treatment of hepatitis C virus infection.

MeSH terms

  • Catalysis
  • Copper / chemistry*
  • Indoles / chemistry*
  • Oxidation-Reduction
  • Spectrum Analysis / methods

Substances

  • Indoles
  • Copper