Pyrrole-2-carboxylic acid as a ligand for the Cu-catalyzed reactions of primary anilines with aryl halides

J Org Chem. 2008 Jul 4;73(13):5167-9. doi: 10.1021/jo8008676. Epub 2008 Jun 11.

Abstract

Pyrrole 2-carboxylic acid (L5) was found to be an effective ligand for the Cu-catalyzed monoarylation of anilines with aryl iodides and bromides. Under the reported conditions (10% CuI/20% L5/DMSO/K3PO 4/80-100 degrees C/20-24 h), a variety of useful functional groups were tolerated, and moderate to good yields of the diaryl amine products were obtained.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Aniline Compounds / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Halogens / chemistry*
  • Hydrocarbons, Cyclic / chemistry*
  • Molecular Structure
  • Proline / analogs & derivatives*
  • Proline / chemistry

Substances

  • Aniline Compounds
  • Halogens
  • Hydrocarbons, Cyclic
  • 2-pyrrolecarboxylic acid
  • Copper
  • Proline