By: William Sommer, Aldrich ChemFiles 2009, 9.5, 3.

Aldrich ChemFiles 2009, 9.5, 3.

The hydroamination reaction allows the introduction of an amine across the triple bond of an alkyne. This atom economic reaction is usually performed at room temperature.1 The challenge resides in the high energy activation needed for the alkyne moiety. One of the ways to make triple bonds more active is to use gold catalysts. They interact with the C–C triple bond of the substrate to render it more nucleophilic.2

Since the first intramolecular hydroamination catalyzed by Na(AuCl4) reported by Fukuda and Utimoto in 1987 (Scheme 1),3 a vast array of alkyne substrates and amines have been used for this reaction over the past decade.

Scheme 1.

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  1. Widenhoefer, R. A. et al. Eur. J. Org. Chem. 2006, 4555.
  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. Fukuda, Y. et al. Synthesis 1991, 975 .

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