CuI/Oxalic Diamide Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amines

J Am Chem Soc. 2015 Sep 23;137(37):11942-5. doi: 10.1021/jacs.5b08411. Epub 2015 Sep 11.

Abstract

A class of oxalic diamides are found to be effective ligands for promoting CuI-catalyzed aryl amination with less reactive (hetero)aryl chlorides. The reaction proceeds at 120 °C with K3PO4 as the base in DMSO to afford a wide range of (hetero)aryl amines in good to excellent yields. The bis(N-aryl) substituted oxalamides are superior ligands to N-aryl-N'-alkyl substituted or bis(N-alkyl) substituted oxalamides. Both the electronic nature and the steric property of the aromatic rings in ligands are important for their efficiency.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Catalysis
  • Chlorine / chemistry*
  • Copper / chemistry*
  • Diamide / chemistry*
  • Iodides / chemistry*
  • Oxalic Acid / chemistry*

Substances

  • Amines
  • Iodides
  • Diamide
  • Chlorine
  • Copper
  • cuprous iodide
  • Oxalic Acid