A beta-keto ester as a novel, efficient, and versatile ligand for copper(I)-catalyzed C-N, C-O, and C-S coupling reactions

J Org Chem. 2007 May 11;72(10):3863-7. doi: 10.1021/jo070443m. Epub 2007 Apr 14.

Abstract

Employing ethyl 2-oxocyclohexanecarboxylate as a novel, efficient, and versatile ligand, the copper-catalyzed coupling reactions of various N/O/S nucleophilic reagents with aryl halides could be successfully carried out under mild conditions. A variety of products including N-arylamides, N-arylimidazoles, aryl ethers, and aryl thioethers were synthesized in good to excellent yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Carbon / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Esters / chemistry*
  • Ligands
  • Molecular Structure
  • Nitrogen / chemistry*
  • Oxygen / chemistry*
  • Pyrrolidinones / chemistry
  • Sulfhydryl Compounds / chemistry
  • Sulfur / chemistry*

Substances

  • Amides
  • Esters
  • Ligands
  • Pyrrolidinones
  • Sulfhydryl Compounds
  • Sulfur
  • Carbon
  • Copper
  • 2-pyrrolidone
  • Nitrogen
  • Oxygen