Asymmetric transfer hydrogenation of ketones using Ru(0) nanoparticles modified by Chiral Thiones

Din Reshi, NU and Senthurpandi, D and Samuelson, AG (2019) Asymmetric transfer hydrogenation of ketones using Ru(0) nanoparticles modified by Chiral Thiones. In: Applied Organometallic Chemistry .

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Abstract

The catalytic asymmetric transfer hydrogenation (ATH) of acetophenone in isopropanol by Ru(0) nanoparticles (NPs) obtained by the in-situ reduction of Ru (II) half-sandwich complexes of chiral 2-oxazolidinethiones and 2-thiozolidinethiones was examined and compared with the catalytic activity of Ru(0) NPs formed in-situ by the reduction of Ru(p-cymene)(Cl) 2 2 in presence of optically active ligands such as (S)-4-isobutylthiazolidine-2-thione, (S)-4-Isopropyl-2(�2-pyridinyl)-2-oxazoline, (8S, 9R)-(�)-cinchonidine, (S)-leucinol, (S)-phenylalaninol, and (S)-leucine. Three of the best catalytic systems were then examined for ATH of thirteen aromatic ketones with different electronic and steric properties. A maximum of 24% ee was obtained using NPs generated from the Ru (II) half-sandwich complex with (S)-4-isobutylthiazolidine-2-thione in the TH of acetophenone. The NPs were characterized by TEM and DLS measurements. Kinetic studies and poisoning experiments confirmed that the reaction is catalyzed by the chiral NPs formed in-situ. Complete characterization of the complexes, including the X-ray crystallographic characterization of two complexes, was also carried out. © 2019 John Wiley & Sons, Ltd.

Item Type:	Journal Article
Publication:	Applied Organometallic Chemistry
Publisher:	John Wiley and Sons Ltd
Additional Information:	Copyright for this article belongs to John Wiley and Sons Ltd.
Keywords:	Amino acids; Catalyst activity; Hydrogenation; Ketones; Nanoparticles; X ray crystallography, Asymmetric transfer hydrogenation; Catalytic asymmetric transfer hydrogenations; Catalytic system; Crystallographic characterization; DLS measurements; Half-sandwich complexes; Nanoparticle (NPs); Steric properties, Ruthenium compounds
Department/Centre:	Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	09 Apr 2019 06:29
Last Modified:	09 Apr 2019 06:29
URI:	http://eprints.iisc.ac.in/id/eprint/62170

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