Progress in the palladium-catalyzed cyanation of aryl chlorides

Mark Sundermeier, Alexander Zapf, Sateesh Mutyala, Wolfgang Baumann, Jürgen Sans, Stefan Weiss, Matthias Beller

Research output: Contribution to journalArticlepeer-review

184 Scopus citations

Abstract

The development of new palladium catalysts for the cyanation of various aryl and heteroaryl chlorides is described. The combination of amine co-catalysts with chelating phosphine ligands, for example, 1,4-bis(diphenylphosphino)butane (dppb) or 1,5-bis(diphenylphosphino)pentane (dpppe), allows an efficient cyanation of chloroarenes with simple potassium cyanide. General palladium-catalyzed cyanation of nonactivated and deactivated chloroarenes is possible for the first time. Studies of the oxidative addition of aryl halides to palladium triphenylphosphine complexes in the presence and absence of amines suggest that the co-catalyst is capable of preventing catalyst deactivation caused by the presence of excess cyanide ions in solution.

Original languageEnglish
Pages (from-to)1828-1836
Number of pages9
JournalChemistry - A European Journal
Volume9
Issue number8
DOIs
StatePublished - 14 Apr 2003
Externally publishedYes

Keywords

  • Aryl chlorides
  • Benzonitriles
  • Cyanation
  • Homogeneous catalysis
  • Palladium

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