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Hydration of Terminal Alkynes Catalyzed by Water-Soluble Cobalt Porphyrin Complexes

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journal contribution
posted on 09.01.2013, 00:00 by Tadashi Tachinami, Takuho Nishimura, Richiro Ushimaru, Ryoji Noyori, Hiroshi Naka
Water-soluble cobalt­(III) porphyrin complexes were found to promote the hydration of terminal alkynes to give methyl ketones. The alkyne hydration proceeded in good to excellent yield with 0.1 to 2 mol % cobalt catalyst 1 and 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 nitro, iodo, and acetal groups. Some of the alkyne substrates tested here are otherwise difficult to hydrate. The alkyne hydration can be performed on a gram scale, and the catalyst can be recovered by aqueous workup.