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Imidazolium ion tethered TsDPENs as efficient water-soluble ligands for rhodium catalyzed asymmetric transfer hydrogenation of aromatic ketones |
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| Affiliation: | 1. Laboratório de Química Orgânica e Biocatálise, Instituto de Química de São Carlos, Universidade de São Paulo, Av. João Dagnone, 1100, J. Santa Angelina, 13563-120, São Carlos, SP, Brazil;2. Instituto de Química, Departamento de Química Fundamental, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, 05508-000 São Paulo, SP, Brazil;3. Instituto de Ciências Ambientais, Químicas e Farmacêuticas,Universidade Federal de São Paulo, Av. Prof. Artur Riedel, 275, 09972-270 Diadema, SP, Brazil |
| Abstract: | An imidazolium ion tethered TsDPEN has been synthesized readily and used as a water-soluble ligand for Cp*RhCl2]2 catalyzed asymmetric transfer hydrogenation (ATH) of aromatic ketones in water. This process provided the secondary alcohols in moderate to excellent conversions (up to 100%) with high enantioselectivities (up to 98% ee) under mild reaction conditions without adding any surfactants. The catalytic system is highly effective with the substrate to catalyst (S/C) ratio of 500 and low hydride donor loading of 1.5 equiv. of HCO2Na. The procedure presented is simple and makes this method suitable for practical use. |
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