Publication

A comparison of ruthenium-catalysed arene hydrogenation reactions in water and 1-alkyl-3-methylimidazolium tetrafluoroborate ionic liquids

Gabor Laurenczy
2003
Journal Articles

Abstract

The hydrogenation of benzene and other arene substrates under biphasic conditions is evaluated using the catalyst precursor Ru(eta(6)-C10H14)(pta)Cl-2 (pta = 1,3,5-triaza-7-phosphaadamantane) immobilised in water and 1-alkyl-3-methylimidazolium tetrafluoroborate ionic liquids. The effect that contamination of the 1-alkyl-3-methylimidazolium tetrafluoroborate ionic liquids with chloride has on the hydrogenation reaction has also been examined. Of the immobilisation solvents tested the optimum solvent was found to be chloride-free 1-butyl-3-methylimidazolium tetrafluoroborate. Catalytic turnovers in this solvent are highest, and in general, turnovers for the hydrogenation reactions follow the trend: chloride-free 1-butyl-3-methylimidazolium tetrafluoroborate > water > chloride-contaminated 1-butyl-3-methylimidazolium tetrafluoroborate.

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https://infoscience.epfl.ch/entities/publication/08dc9d72-5de2-4b37-b4d1-f5a0aef76195

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Gabor Laurenczy
2003
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/08dc9d72-5de2-4b37-b4d1-f5a0aef76195

About this result

Related concepts (20)

Transfer hydrogenation

In chemistry, transfer hydrogenation is a chemical reaction involving the addition of hydrogen to a compound from a source other than molecular . It is applied in laboratory and industrial organic synthesis to saturate organic compounds and reduce ketones to alcohols, and imines to amines. It avoids the need for high-pressure molecular used in conventional hydrogenation. Transfer hydrogenation usually occurs at mild temperature and pressure conditions using organic or organometallic catalysts, many of which are chiral, allowing efficient asymmetric synthesis.

Hydrogenation

Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically constitutes the addition of pairs of hydrogen atoms to a molecule, often an alkene. Catalysts are required for the reaction to be usable; non-catalytic hydrogenation takes place only at very high temperatures.

Asymmetric hydrogenation

Asymmetric hydrogenation is a chemical reaction that adds two atoms of hydrogen to a target (substrate) molecule with three-dimensional spatial selectivity. Critically, this selectivity does not come from the target molecule itself, but from other reagents or catalysts present in the reaction. This allows spatial information (what chemists refer to as chirality) to transfer from one molecule to the target, forming the product as a single enantiomer.

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A comparison of ruthenium-catalysed arene hydrogenation reactions in water and 1-alkyl-3-methylimidazolium tetrafluoroborate ionic liquids

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