Biphasic Glycerol/2-MeTHF, Ruthenium-Catalysed Enantioselective Transfer Hydrogenation of Ketones Using Sodium Hypophosphite as Hydrogen Donor - Archive ouverte HAL Access content directly
Journal Articles European Journal of Organic Chemistry Year : 2013

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

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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Dates and versions

hal-03249234 , version 1 (04-06-2021)

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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, 2013, 2013 (24), pp.5439-5444. ⟨10.1002/ejoc.201300506⟩. ⟨hal-03249234⟩
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