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

  1. Aaron J. Yap1,
  2. Dr. Bun Chan2,
  3. Dr. Alexander K. L. Yuen1,
  4. Dr. Antony J. Ward1,
  5. Prof. Anthony F. Masters1,
  6. Prof. Thomas Maschmeyer1,*

Article first published online: 8 JUL 2011

DOI: 10.1002/cctc.201100076

Issue

ChemCatChem

ChemCatChem

Volume 3, Issue 9, pages 1496–1502, September 19, 2011

Additional Information

How to Cite

Yap, A. J., Chan, B., Yuen, A. K. L., Ward, A. J., Masters, A. F. and Maschmeyer, T. (2011), A Palladium-Catalyzed Multicascade Reaction: Facile Low-Temperature Hydrogenolysis of Activated Nitriles and Related Functional Groups. ChemCatChem, 3: 1496–1502. doi: 10.1002/cctc.201100076

Author Information

  1. 1

    Laboratory of Advanced Catalysis for Sustainability, Building F11, School of Chemistry, University of Sydney, Sydney 2006 (Australia), Fax: (+61) 2-9351-3329

  2. 2

    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

*Laboratory of Advanced Catalysis for Sustainability, Building F11, School of Chemistry, University of Sydney, Sydney 2006 (Australia), Fax: (+61) 2-9351-3329

Publication History

  1. Issue published online: 14 SEP 2011
  2. Article first published online: 8 JUL 2011
  3. Manuscript Revised: 25 MAY 2011
  4. Manuscript Received: 1 MAR 2011

Funded by

  • Australian Research Council

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Keywords:

  • ab initio calculations;
  • amines;
  • catalysis;
  • hydrogenation;
  • palladium

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.

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