1. Catalytic Reduction of Amides Avoiding LiAlH4 OR B2H6

  1. Peter J. Dunn3,
  2. K. K. (Mimi) Hii4,
  3. Michael J. Krische5 and
  4. Michael T. Williams6
  1. Deborah L. Dodds1 and
  2. David J. Cole-Hamilton2

Published Online: 23 MAY 2013

DOI: 10.1002/9781118354520.ch01

Sustainable Catalysis: Challenges and Practices for the Pharmaceutical and Fine Chemical Industries

Sustainable Catalysis: Challenges and Practices for the Pharmaceutical and Fine Chemical Industries

How to Cite

Dodds, D. L. and Cole-Hamilton, D. J. (2013) Catalytic Reduction of Amides Avoiding LiAlH4 OR B2H6, in Sustainable Catalysis: Challenges and Practices for the Pharmaceutical and Fine Chemical Industries (eds P. J. Dunn, K. K. (. Hii, M. J. Krische and M. T. Williams), John Wiley & Sons, Inc., Hoboken, New Jersey. doi: 10.1002/9781118354520.ch01

Editor Information

  1. 3

    Pfizer Green Chemistry Lead, Sandwich, Kent, United Kingdom

  2. 4

    Imperial College London, South Kensington, London, United Kingdom

  3. 5

    University of Texas at Austin, Austin, Texas, United States of America

  4. 6

    CMC Consultant, Deal, Kent, United Kingdom

Author Information

  1. 1

    School of Chemistry, University of St. Andrews, North Haugh, Fife, Scotland, UK

  2. 2

    Johnson Matthey plc, Billingham, UK

Publication History

  1. Published Online: 23 MAY 2013
  2. Published Print: 8 APR 2013

ISBN Information

Print ISBN: 9781118155424

Online ISBN: 9781118354520

SEARCH

Keywords:

  • amides;
  • catalytic reduction;
  • heterogeneous amide hydrogenation;
  • homogeneous amide hydrogenation;
  • hydrosilation;
  • pharmaceutical industry;
  • stoichiometric metal hydride reagents

Summary

Amines are key components in a variety of pharmaceutical compounds, chemical intermediates, and commodity chemicals. This chapter focuses primarily on the synthesis of amines via homogeneous and heterogeneous amide hydrogenation. Particular aspects considered are the atom economy (AE) of the reactions, the operating conditions, and the safety of the reagents/processes. The chapter describes some examples to highlight the various challenges faced by the synthetic chemists in the reduction of a molecule with multiple functional groups. It also explains the use of silanes as a hydride source in amide reductions. These catalyzed processes are then compared with stoichiometric metal hydride reagents such as lithium aluminum hydride (LiAlH4) or borane (B2H6).