3. Catalytic Nucleophilic Additions of Alkynes in Water

  1. Prof. Dr. Pierre H. Dixneuf2,3 and
  2. Dr. Victorio Cadierno4
  1. Xiaoquan Yao and
  2. Chao-Jun Li

Published Online: 4 JAN 2013

DOI: 10.1002/9783527656790.ch3

Metal-Catalyzed Reactions in Water

Metal-Catalyzed Reactions in Water

How to Cite

Yao, X. and Li, C.-J. (2013) Catalytic Nucleophilic Additions of Alkynes in Water, in Metal-Catalyzed Reactions in Water (eds P. H. Dixneuf and V. Cadierno), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany. doi: 10.1002/9783527656790.ch3

Editor Information

  1. 2

    CNRS-Université de Rennes 1, Catalyse et Organométalliques, Campus de Beaulieu, Bat10c, 35042 Rennes Cedex, France

  2. 3

    UMR 6226: CNRS – Université de Rennes, Laboratoire “Organométalliques, Matériaux, Catalyse”, Institut Sciences Chimiques de Rennes, 35042 Rennes, France

  3. 4

    Universidad de Oviedo, Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Química Organometálica, “Enrique Moles” (Unidad Asociada al CSIC), Facultad de Química, Julían Clavería 8, 33006 Oviedo, Spain

Author Information

  1. McGill University, Department of Chemistry, Green Chemistry and Organic, Synthesis Laboratory, 801 Sherbroke Street West, Montreal, Quebec H3A 2K6, Canada

Publication History

  1. Published Online: 4 JAN 2013
  2. Published Print: 16 JAN 2013

ISBN Information

Print ISBN: 9783527331888

Online ISBN: 9783527656790

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Keywords:

  • terminal alkynes;
  • unsaturated electrophiles;
  • catalytic nucleophilic addition;
  • ligand promotion;
  • phosphine ligand

Summary

As an example of Grignard-type reaction, the catalytic nucleophilic addition of terminal alkynes to unsaturated electrophiles in water provides an efficient and atom-economical alternative to the classical alkyne reactions. In this chapter, the development of catalytic direct nucleophilic additions of terminal alkynes in the past decade is described. Three types of reactions are discussed: (1) catalytic nucleophilic additions of terminal alkynes with carbonyl derivatives (including acid chloride, aldehydes, and ketones); (2) catalytic addition of alkynes to C=N bonds; and (3) catalytic conjugate additions.