7. OH Activation for Nucleophilic Substitution

  1. Peter J. Dunn2,
  2. K. K. (Mimi) Hii3,
  3. Michael J. Krische4 and
  4. Michael T. Williams5
  1. Jonathan M.J. Williams

Published Online: 23 MAY 2013

DOI: 10.1002/9781118354520.ch07

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

Williams, J. M.J. (2013) OH Activation for Nucleophilic Substitution, 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.ch07

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, University of Bath, Claverton Down, Bath, 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:

  • alcohols;
  • alkylating agents;
  • C[BOND]N bonds;
  • C[BOND]C bonds;
  • hydroxyl group;
  • nucleophilic substitution

Summary

The wide availability of alcohols makes them useful building blocks in synthesis. It is generally necessary to activate the alcohol in order to facilitate nucleophilic substitution reactions for the construction of new C[BOND]C or C[BOND]N bonds. The activation of alcohols by the temporary removal of hydrogen has attracted a lot of attention from many research groups. Although the reactions showed considerable scope, substrates that act as good ligands for the catalyst tend to need higher catalyst loadings and temperatures in order to be successful. In general, relatively high temperatures and catalyst loading are required even for simple substrates. The identification of simple, cheap catalysts capable of achieving these reactions under milder conditions, ideally room temperature, remains a goal for using alcohols as alkylating agents.