Progress in the Palladium‐Catalyzed Cyanation of Aryl Chlorides
- 8 April 2003
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 9 (8), 1828-1836
- https://doi.org/10.1002/chem.200390210
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.Keywords
This publication has 84 references indexed in Scilit:
- Suzuki−Miyaura Cross-Coupling Reactions Mediated by Palladium/Imidazolium Salt SystemsOrganometallics, 2002
- Efficient Palladium-Catalyzed Alkoxycarbonylation of N-Heteroaryl Chlorides - A Practical Synthesis of Building Blocks for Pharmaceuticals and HerbicidesSynthesis, 2001
- Efficient Synthesis of Fine Chemicals and Organic Building Blocks Applying Palladium-Catalyzed Coupling ReactionsChemical Engineering & Technology, 2001
- Phenyl Backbone-Derived P,O- and P,N-Ligands for Palladium/Ligand-Catalyzed Aminations of Aryl Bromides, Iodides, and Chlorides. Syntheses and Structures of (P,O)n-Palladium(II)Aryl(Br) ComplexesOrganometallics, 1999
- Palladacyclen als effiziente Katalysatoren für ArylkupplungsreaktionenAngewandte Chemie, 1995
- The Cyanation of Aromatic Halides Catalyzed by Nickel(0) Complexes Generated In Situ. I. General Scope and LimitationsBulletin of the Chemical Society of Japan, 1988
- Einführung der Cyano-Gruppe in PyrazineSynthesis, 1981
- Alumina Assisted Aryl CyanationThe Journal of Organic Chemistry, 1979
- Nucleophilic Displacement Catalyzed by Transition Metal. III. Kinetic Investigation of the Cyanation of Iodobenzene Catalyzed by Palladium(II)Bulletin of the Chemical Society of Japan, 1976
- PALLADIUM(II) CATALYZED SYNTHESIS OF ARYL CYANIDES FROM ARYL HALIDESChemistry Letters, 1973