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

doi:10.1002/asia.200900527

Paper

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

Published Mar 1, 2010 · H. Maytum, J. Francos, David J. Whatrup

Chemistry, an Asian journal

UNKNOWN SJR score

34

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Abstract

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.

Study Snapshot

1,4-Butanediol acts as a reducing agent in transfer hydrogenation reactions, enabling the reduction of ketones, imines, and alkenes to saturated alcohols, imines, and alkenes.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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

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References

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Glycerol is a green solvent and hydrogen donor in catalytic transfer hydrogenation-dehydrogenation reactions, allowing easy product separation and catalyst recycling.

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Transition metal catalysts can enhance the reactivity of alcohols by temporarily removing hydrogen, resulting in intermediate aldehyde or ketone compounds with greater reactivity towards nucleophilic addition.

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Succinic acid shows potential as a renewable platform chemical for biobased polymers, but further improvements are needed for economically favorable production.

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1,4-alkynediols can be converted into 2,5-disubstituted furans using a ruthenium-based catalyst and Xantphos at 1 mol% loading.

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This study demonstrates the successful synthesis of 1,2,5-substituted pyrroles from 1,4-alkynediols using ruthenium-catalyzed isomerisation, offering potential for pharmaceutical applications.

Borrowing hydrogen in the activation of alcohols

Metal-catalyzed removal of hydrogen from alcohols can convert them into carbonyl compounds, which can then be transformed into imines, alkenes, and -functionalized carbonyl compounds.

Oxidation of alcohols by transfer hydrogenation: driving the equilibrium with an intramolecular trap

Levulinic acid and its esters can act as an oxidant for alcohols by undergoing transfer hydrogenation, reducing the need for large amounts of reagents.

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