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Synfacts 2022; 18(01): 0063
DOI: 10.1055/s-0041-1737317
Metals in Synthesis

Gold(III)-Catalyzed Hydration of Alkynes

Contributor(s):
Mark Lautens
,
Jeanne Masson-Makdissi
Fukuda Y, Utimoto K. * Kyoto University, Japan
Effective Transformation of Unactivated Alkynes into Ketones or Acetals with a Gold(III) Catalyst.

J. Org. Chem. 1991;
56: 3729-3731
DOI: 10.1021/jo00011a058.
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Key words

hydration - alkynes - gold catalysis

Significance

In 1991, Fukuda and Utimoto disclosed the gold(III)-catalyzed hydration of alkynes. In contrast to traditional Hg(II)-mediated hydrations that require strongly acidic conditions, the reported Au(III)-catalyzed protocol is much milder and does not require any acid, allowing for increased functional group tolerance.


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Comment

The hydration reaction is operationally simple, requiring only 2 mol% of Au(III) catalyst in a refluxing mixture of methanol and water. When strictly anhydrous methanol is used, the corresponding dimethyl acetal product is obtained in place of the ketone.


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Review

Z. Li, C. Brouwer, C. He Chem. Rev. 2008, 108, 3239–3265.


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Publication History

Article published online:
17 December 2021

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