Get access

A Palladium-Catalyzed Multicascade Reaction: Facile Low-Temperature Hydrogenolysis of Activated Nitriles and Related Functional Groups

Authors

  • Aaron J. Yap,

    1. Laboratory of Advanced Catalysis for Sustainability, Building F11, School of Chemistry, University of Sydney, Sydney 2006 (Australia), Fax: (+61) 2-9351-3329
    Search for more papers by this author
  • Dr. Bun Chan,

    1. ARC Center of Excellence for Free Radical Chemistry and Biotechnology Building F11, School of Chemistry, University of Sydney, Sydney 2006 (Australia), Fax: (+61) 2-9351-3329
    Search for more papers by this author
  • Dr. Alexander K. L. Yuen,

    1. Laboratory of Advanced Catalysis for Sustainability, Building F11, School of Chemistry, University of Sydney, Sydney 2006 (Australia), Fax: (+61) 2-9351-3329
    Search for more papers by this author
  • Dr. Antony J. Ward,

    1. Laboratory of Advanced Catalysis for Sustainability, Building F11, School of Chemistry, University of Sydney, Sydney 2006 (Australia), Fax: (+61) 2-9351-3329
    Search for more papers by this author
  • Prof. Anthony F. Masters,

    1. Laboratory of Advanced Catalysis for Sustainability, Building F11, School of Chemistry, University of Sydney, Sydney 2006 (Australia), Fax: (+61) 2-9351-3329
    Search for more papers by this author
  • Prof. Thomas Maschmeyer

    Corresponding author
    1. Laboratory of Advanced Catalysis for Sustainability, Building F11, School of Chemistry, University of Sydney, Sydney 2006 (Australia), Fax: (+61) 2-9351-3329
    • Laboratory of Advanced Catalysis for Sustainability, Building F11, School of Chemistry, University of Sydney, Sydney 2006 (Australia), Fax: (+61) 2-9351-3329
    Search for more papers by this author

Abstract

The facile hydrogenolysis of various nitriles, imines, and amines over Pd/C has been achieved by using straightforward and relatively mild conditions. Substrates that contain an aryl group adjacent to the nitrogen-containing functionality were hydrogenolyzed most effectively. The stabilization of the proposed η2-coordinated palladium intermediate by this group was partly responsible for this observation and is borne out by ab initio calculations.

Get access to the full text of this article

Ancillary