1,4-Butanediol as a reducing agent in transfer hydrogenation reactions

1,4-Butanediol is able to deliver two equivalents of H(2) in hydrogen-transfer reactions to ketones, imines, and alkenes. Unlike simple alcohols, which establish equilibrium in the reduction of ketones, 1,4-butanediol acts essentially irreversibly owing to the formation of butyrolactone, which acts...

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Published inChemistry, an Asian journal Vol. 5; no. 3; p. 538
Main Authors Maytum, Hannah C, Francos, Javier, Whatrup, David J, Williams, Jonathan M J
Format Journal Article
LanguageEnglish
Published Germany 01.03.2010
Subjects
Alkenes - chemistry
Butylene Glycols - chemistry
Hydrogenation
Imines - chemistry
Isomerism
Lactones - chemistry
Propanols - chemistry
Reducing Agents - chemistry
Ruthenium - chemistry
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Summary:1,4-Butanediol is able to deliver two equivalents of H(2) in hydrogen-transfer reactions to ketones, imines, and alkenes. Unlike simple alcohols, which establish equilibrium in the reduction of ketones, 1,4-butanediol acts essentially irreversibly owing to the formation of butyrolactone, which acts as a thermodynamic sink. It is therefore not necessary to use 1,4-butanediol in great excess in order to achieve reduction reactions. In addition, allylic alcohols are reduced to saturated alcohols through an isomerization/reduction sequence using a ruthenium catalyst with 1,4-butanediol as the reducing agent. Imines and alkenes are also reduced under similar conditions.
ISSN:1861-471X
DOI:10.1002/asia.200900527