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

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 function...

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Published inJournal of the American Chemical Society Vol. 135; no. 1; pp. 50 - 53
Main Authors Tachinami, Tadashi, Nishimura, Takuho, Ushimaru, Richiro, Noyori, Ryoji, Naka, Hiroshi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 09.01.2013
Amer Chemical Soc
Subjects
Alkynes - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cobalt - chemistry
Ketones - chemical synthesis
Ketones - chemistry
Metalloporphyrins - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Solubility
Water - chemistry
GOLD(I) COMPLEXES
ALCOHOLS
TRANSFORMATION
EPOXIDES
METHANOL
HYDROLYTIC KINETIC RESOLUTION
ANTI-MARKOVNIKOV HYDRATION
METAL
ALDEHYDES
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja310282t