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DOI: 10.1055/s-0041-1737317
Gold(III)-Catalyzed Hydration of Alkynes
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
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.
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.
Review
Z. Li, C. Brouwer, C. He Chem. Rev. 2008, 108, 3239–3265.
Publication History
Article published online:
17 December 2021
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