Riboflavin as Photoredox Catalyst in the Cyclization of Thiobenzanilides: Synthesis of 2-Substituted Benzothiazoles

Org Lett. 2020 Jan 17;22(2):610-614. doi: 10.1021/acs.orglett.9b04384. Epub 2019 Dec 30.

Abstract

Benzothiazoles are synthesized from thiobenzanilides using riboflavin as a photosensitizer and potassium peroxydisulfate as a sacrificial oxidizing agent under visible light irradiation. The methodology accepts a broad range of functional groups and affords the 2-substituted benzothiazoles by transition-metal-free organic photoredox catalysis under very mild conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anilides / chemistry*
  • Benzothiazoles / chemical synthesis*
  • Benzothiazoles / chemistry
  • Catalysis
  • Cyclization
  • Molecular Structure
  • Oxidation-Reduction
  • Photochemical Processes
  • Riboflavin / chemistry*

Substances

  • Anilides
  • Benzothiazoles
  • benzanilide
  • Riboflavin