Chelation-assisted palladium-catalyzed cascade bromination/cyanation reaction of 2-arylpyridine and 1-arylpyrazole C-H bonds

J Org Chem. 2009 Dec 18;74(24):9470-4. doi: 10.1021/jo902185c.

Abstract

A chelation-assisted palladium-catalyzed cascade bromination/cyanation reaction of 2-arylpyridine and 1-arylpyrazole C-H bonds has been developed. Notably, the reaction employs K(3)[Fe(CN)(6)] as a safe and nontoxic cyanide source, providing aromatic nitriles in moderate to good yields in one-pot. The procedure tolerates methoxy, chloro, fluoro, cyano, trifluoromethyl, and carbomethoxy groups.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / chemical synthesis
  • Benzene Derivatives / chemistry*
  • Carbon / chemistry*
  • Catalysis
  • Chelating Agents / chemistry*
  • Cyanides / chemistry*
  • Ferricyanides / chemistry
  • Halogenation
  • Hydrogen / chemistry*
  • Models, Chemical
  • Nitriles / chemical synthesis
  • Nitriles / chemistry
  • Palladium / chemistry*
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry*
  • Pyridines / chemical synthesis
  • Pyridines / chemistry*

Substances

  • Benzene Derivatives
  • Chelating Agents
  • Cyanides
  • Ferricyanides
  • Nitriles
  • Pyrazoles
  • Pyridines
  • Palladium
  • Carbon
  • Hydrogen
  • potassium ferricyanide