An Iodide-Mediated Anodic Amide Coupling

Chemistry. 2022 Sep 27;28(54):e202201768. doi: 10.1002/chem.202201768. Epub 2022 Aug 22.

Abstract

The ubiquity of amide bonds, present in natural products and common pharmaceuticals renders this functional group one of the most prevalent in organic chemistry. Despite its importance and a wide variety of existing methods for its formation, the latter still can be a challenge for classical activating reagents such as chloridating agents or carbodiimides. As the spent reagents often cannot be recycled, the development of more sustainable methods is highly desirable. Herein, we report an operationally simple and mild indirect electrochemical protocol to effect the condensation of carboxylic acids with amines, forming a wide variety of carboxamides.

Keywords: amides; electrochemistry; iodine; peptide coupling; redox condensation.

MeSH terms

  • Amides* / chemistry
  • Amines / chemistry
  • Biological Products*
  • Carbodiimides / chemistry
  • Carboxylic Acids / chemistry
  • Indicators and Reagents
  • Iodides
  • Pharmaceutical Preparations

Substances

  • Amides
  • Amines
  • Biological Products
  • Carbodiimides
  • Carboxylic Acids
  • Indicators and Reagents
  • Iodides
  • Pharmaceutical Preparations