5. Direct Amide Formation Avoiding Poor Atom Economy Reagents

  1. Peter J. Dunn2,
  2. K. K. (Mimi) Hii3,
  3. Michael J. Krische4 and
  4. Michael T. Williams5
  1. Benjamin M. Monks and
  2. Andrew Whiting

Published Online: 23 MAY 2013

DOI: 10.1002/9781118354520.ch05

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

Monks, B. M. and Whiting, A. (2013) Direct Amide Formation Avoiding Poor Atom Economy Reagents, 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.ch05

Editor Information

  1. 2

    Pfizer Green Chemistry Lead, Sandwich, Kent, United Kingdom

  2. 3

    Imperial College London, South Kensington, London, United Kingdom

  3. 4

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

  4. 5

    CMC Consultant, Deal, Kent, United Kingdom

Author Information

  1. Department of Chemistry, Durham University, Durham, UK

Publication History

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

ISBN Information

Print ISBN: 9781118155424

Online ISBN: 9781118354520

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Keywords:

  • antimony-based reagents;
  • boric acid catalysis;
  • boronic acid-based catalysis;
  • direct amide formation;
  • heterogeneous catalysts;
  • microwave-assisted amide synthesis;
  • poor atom economy reagents;
  • titanium(IV)-based reagents;
  • triazine-based reagents

Summary

In 2005, the American Chemical Society, Green Chemistry Institute, Pharmaceutical Roundtable, which consisted of several prominent pharmaceutical companies, was formed in order to encourage and implement green chemical principles into the global pharmaceutical and chemical industry. The Roundtable highlighted the amide formation reaction as a key process that invariably involved poor atom economy reagents. It was, therefore, highlighted as a key challenge to synthetic chemists to develop greener direct amide formation reactions, starting from carboxylic acids and amines, without the use of stoichiometric and high molecular weight reagents. This chapter presents a survey of recent developments that address these issues. It examines the current state-of-the-art in direct amide formation, mainly involving boronic and boric acid-based systems, being perhaps most developed, though also examining other catalytic solutions, including triazine-based reagents, titanium(IV)-based reagents and antimony-based reagents. It ends with a discussion of heterogeneous catalysts and microwave-assisted amide synthesis.