Palladium-catalyzed decarboxylative cross-coupling reaction between heteroaromatic carboxylic acids and aryl halides

J Org Chem. 2010 Mar 5;75(5):1550-60. doi: 10.1021/jo9022793.

Abstract

A full overview of the decarboxylative cross-coupling reaction between heteroaromatic carboxylic acids and aryl halides is described. This transformation employs palladium catalysts with short reaction times providing facile synthesis of aryl-substituted heteroaromatics. The effect of each reaction parameter including solvent, base, and additive employed as well as the full substrate scope of this transformation are reported. Mechanistic evidence is also disclosed that sheds light on possible reaction pathways.

MeSH terms

  • Carboxylic Acids / chemistry*
  • Catalysis
  • Chlorides / chemistry*
  • Cross-Linking Reagents / chemistry*
  • Cyclization
  • Decarboxylation
  • Heterocyclic Compounds / chemistry*
  • Microwaves
  • Models, Molecular
  • Molecular Structure
  • Palladium / chemistry*
  • Stereoisomerism
  • Temperature

Substances

  • Carboxylic Acids
  • Chlorides
  • Cross-Linking Reagents
  • Heterocyclic Compounds
  • Palladium