Heterogeneous Photocatalytic C-H Functionalization of Indoles with Diazo Compounds Enabled by Carbon Nitride

J Org Chem. 2023 Jul 7;88(13):8703-8708. doi: 10.1021/acs.joc.3c00574. Epub 2023 May 29.

Abstract

Herein, we reported the heterogeneous photocatalytic C-H alkylation of indoles with diazo compounds using graphitic carbon nitride (g-C3N4) as the photocatalyst. The reaction was carried out under a simple operation and mild conditions. In addition, the catalyst was found to be stable and reusable after five reaction cycles. The photochemical reaction proceeds via an intermediary of a carbon radical, which is generated from diazo compounds through a visible-light-promoted proton-coupled electron transfer (PCET) process.

MeSH terms

  • Azo Compounds
  • Carbon
  • Coloring Agents
  • Indoles*
  • Nitriles / chemistry
  • Protons*

Substances

  • Protons
  • cyanogen
  • Indoles
  • Carbon
  • Nitriles
  • Azo Compounds
  • Coloring Agents