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Gold-Catalyzed Addition of HX to Alkynes

Organogold Compounds (2014)

  1. Emilie Genin1,
  2. Veronique Michelet2

Published Online: 22 JUN 2014

DOI: 10.1002/9780470682531.pat0814

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Genin, E. and Michelet, V. 2014. Gold-Catalyzed Addition of HX to Alkynes. Patai's Chemistry of Functional Groups. 1–60.

Author Information

  1. 1

    Institut des Sciences Moléculaires, UMR 5255, Bâtiment A11, Université de Bordeaux 1, Talence Cedex, France

  2. 2

    Institut de Recherche de Chimie Paris, Paris Cedex 05, France

Publication History

  1. Published Online: 22 JUN 2014

Abstract

Among the myriad of organic transformations that have been developed in the area of gold catalysis, the addition of HX to alkynes has been a field of intense investigation. This chapter presents the main and recent contributions in the field of gold-catalyzed nucleophilic addition of HX to alkynes. The presentation includes the addition of O-nucleophiles (including water, alcohols and carboxylic acids), of N-nucleophiles and other heteroatom nucleophiles (including thiols and halogens) to alkynes. The historical background for inter- and intramolecular additions, the domino processes and the applications to natural products synthesis are highlighted.

Keywords:

  • alcohol;
  • alkyne;
  • amide;
  • amine;
  • carboxylic acid;
  • gold;
  • heterocycle;
  • nucleophilic addition;
  • thiol