16. Formation of C[BOND]C BONDS via Catalytic Hydrogenation and Transfer Hydrogenation

  1. Peter J. Dunn3,
  2. K. K. (Mimi) Hii4,
  3. Michael J. Krische5 and
  4. Michael T. Williams6
  1. Joseph Moran1 and
  2. Michael J. Krische2

Published Online: 23 MAY 2013

DOI: 10.1002/9781118354520.ch16

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

Moran, J. and Krische, M. J. (2013) Formation of C[BOND]C BONDS via Catalytic Hydrogenation and Transfer Hydrogenation, 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.ch16

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

    Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, TX, USA

  2. 2

    ISIS, University of Strasbourg, Strasbourg, France

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:

  • aldol reaction;
  • C[BOND]C bonds;
  • carbonyl allylation;
  • carbonyl vinylation;
  • catalytic hydrogenation;
  • imine vinylation;
  • Mannich reaction;
  • propargylation;
  • transfer hydrogenation

Summary

This chapter talks about the formation of C[BOND]C bonds via catalytic hydrogenation and transfer hydrogenation. It is found that diverse p-unsaturated reactants are reductively coupled to polarized C[DOUBLE BOND]X (X[DOUBLE BOND]O, NR) bonds under hydrogenation conditions, offering an alternative to stoichiometric organometallic reagents in a broad range of carbonyl and imine additions. This concept is extended further by related transfer hydrogenative processes, for which hydrogen exchange between alcohols and p-unsaturated reactants triggers the generation of electrophile-nucleophile pairs that combine to form products of carbonyl addition directly from the alcohol oxidation level. The chapter also talks about carbonyl and imine vinylation, carbonyl allylation and propargylation, and aldol, Mannich, and related processes in detail.