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Biphasic Glycerol/2-MeTHF, Ruthenium-Catalysed Enantioselective Transfer Hydrogenation of Ketones Using Sodium Hypophosphite as Hydrogen Donor

Carole Guyon 1 Estelle Métay 1 Nicolas Duguet 1 Marc Lemaire 1
1 CASYEN - Catalyse Synthèse et Environnement
ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
Abstract : Sodium hypophosphite has been used as an efficient hydrogen donor in the transfer hydrogenation of aliphatic and aromatic ketones in the presence of [RuCl2(p-cymene)]2 and 2,2′-bipyridine in water. The corresponding alcohols were isolated in moderate to excellent yields (39–95 %). Good chemoselectivity was observed with ester, nitrile and halide functionalities in the ketones not being reduced. An enantioselective version of the reaction using [RuCl(p-cymene){(R,R)-TsDPEN}] as catalyst in a glycerol/2-MeTHF biphasic solvent mixture has been developed and allowed the reduction of (hetero)aromatic ketones with excellent chemo- and enantioselectivities (up to 97 % ee).
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Submitted on : Friday, June 4, 2021 - 8:59:13 AM
Last modification on : Saturday, June 5, 2021 - 3:26:08 AM

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Carole Guyon, Estelle Métay, Nicolas Duguet, Marc Lemaire. Biphasic Glycerol/2-MeTHF, Ruthenium-Catalysed Enantioselective Transfer Hydrogenation of Ketones Using Sodium Hypophosphite as Hydrogen Donor. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2013, 2013 (24), pp.5439-5444. ⟨10.1002/ejoc.201300506⟩. ⟨hal-03249234⟩

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