Amide Bond Formation via Aerobic Photooxidative Coupling of Aldehydes with Amines Catalyzed by a Riboflavin Derivative

Org Lett. 2021 Sep 3;23(17):6825-6830. doi: 10.1021/acs.orglett.1c02391. Epub 2021 Aug 23.

Abstract

We report an effective, operationally simple, and environmentally friendly system for the synthesis of tertiary amides by the oxidative coupling of aromatic or aliphatic aldehydes with amines mediated by riboflavin tetraacetate (RFTA), an inexpensive organic photocatalyst, and visible light using oxygen as the sole oxidant. The method is based on the oxidative power of an excited flavin catalyst and the relatively low oxidation potential of the hemiaminal formed by amine to aldehyde addition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amines / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Riboflavin / analogs & derivatives*
  • Riboflavin / chemical synthesis
  • Riboflavin / chemistry

Substances

  • Aldehydes
  • Amides
  • Amines
  • 2',3',4',5'-tetraacetylriboflavin
  • Riboflavin