Nucleophilic Addition to Alkynes

By: William Sommer, Chemfiles Volume 9 Article 5

Alkynes have been some of the first substrates used in gold catalysis. The first report dates back to 1976 from Thomas and coworkers for the oxidation of alkynes using H[AuCl4].1Since then, alkynes became substrates of choice for various transformations catalyzed by gold.2,3 The gold acts as a Lewis acid activating the π-system, facilitating the addition of the nucleophile (Figure 1).2 In this section, examples of hydroamination, hydroalkylation and intermolecular annulation of various alkynes using a variety of gold complexes are described.

Figure 1: gold acts as a Lewis acid activating the π-system, facilitating the addition of the nucleophile

Figure 1.

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References

  1. Norman, R. O. C. et al. J. Chem. Soc. Perkin Trans. 1 1996, 1983
  2. (a) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180. (b) Jiménez-Núñez, E. et al. Chem. Commun. 2007, 333. (c) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2006, 45, 7896.
  3. Hashmi, A. S. K. Gold Bull. 2003, 36, 3.

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