Hydration of organic compounds catalyzed by metal porphyrins

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We have developed water-soluble cobalt(III) porphyrin complexes that promote the hydration of terminal alkynes to produce methyl ketones. The alkyne hydration was compatible with the presence of acid/base- or redox-sensitive functional groups such as alkyl silyl ethers; allyl ethers; trityl ethers; benzyl ethers; carboxylic esters; boronic esters; carboxamides; nitriles; and acetal groups. Some of the alkyne substrates tested here are otherwise difficult to hydrate. The reaction mechanism was also clarified using spectroscopic, kinetic, and theoretical methods.