Aerobic oxidative amidation of aromatic and cinnamic aldehydes with secondary amines by CuI/2-pyridonate catalytic system

J Org Chem. 2012 Oct 19;77(20):9102-9. doi: 10.1021/jo301553v. Epub 2012 Sep 25.

Abstract

A simple and convenient CuI/2-pyridonate catalytic system for the oxidative amidation of aldehydes with secondary amines has been developed. With this system, a variety of useful arylamides have been synthesized in moderate to good yields in the presence of small amount of copper catalyst and the pyridonate ligand, generating only water as a coproduct. Synthesis of cinnamamides was also achieved by the reactions of cinnamaldehydes with secondary amines in moderate yields. Air was successfully employed as a green oxidant in this catalytic system, achieving a safe and atom-efficient system for the synthesis of amides.

MeSH terms

  • Aldehydes / chemistry*
  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amines / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Iodides / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Pyridones / chemistry*

Substances

  • Aldehydes
  • Amides
  • Amines
  • Iodides
  • Pyridones
  • Copper
  • cuprous iodide