Alkyne Hydration

By: William Sommer, Aldrich ChemFiles 2009, 9.5, 6.

Aldrich ChemFiles 2009, 9.5, 6.

The hydration of alkynes has been extensively studied for more than 100 years. This reation allows access to various carbonyl derivatives starting from alkynes. Nolan and coworkers reported the acid-free catalyzed alkyne hydration using a gold catalyst.1 Nolan has been one of the pioneers of the use of N-heterocyclic carbenes (NHC) as ligands in various catalytic transformation using a variety of metals. Using a gold-NHC complex and silver hexafluoroantimonate, the authors demonstrated the outstanding activity of this catalyst in the hydration of various alkynes using 1,4-dioxane and methanol as reaction media (Scheme 14). It is important to note that an acid is not needed for this transformation and that catalyst loadings as low as 10 ppm were used for this reaction.

Scheme 14.

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  1. Marion, N. et al. J. Am. Chem. Soc. 2009, 131, 448.

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