Organic-Dye-Catalyzed Visible-Light-Mediated Regioselective C-3 Alkoxycarbonylation of Imidazopyridines by Carbazates

J Org Chem. 2022 Nov 4;87(21):14915-14922. doi: 10.1021/acs.joc.2c01742. Epub 2022 Oct 9.

Abstract

A mild and eco-friendly visible-light-mediated regioselective C-H alkoxycarbonylation of imidazo[1,2-a]pyridine heterocycles using rose bengal as a photoredox catalyst at room temperature has been developed. Biologically important alkoxycarboxylated imidazo[1,2-a]pyridines at the C-3 position as well as coumarins and quinoxalin-2(1H)-ones have been prepared. The present approach has the advantage of having a user- and eco-friendly catalyst, a carbonyl source, as well as extremely mild conditions for direct and regioselective C-H alkoxycarbonylation mediated by visible light as a green energy source.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Light*
  • Molecular Structure
  • Pyridines*
  • Stereoisomerism

Substances

  • imidazopyridine
  • carbazic acid
  • Pyridines