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Orientation towards asymmetric transfer hydrogenation of ketones catalyzed by (pyrazolyl)ethyl)pyridine Fe(II) and Ni(II) complexes

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Abstract Compounds 2-[1-(3,5-dimethylpyrazol-1-yl)ethyl]pyridine (L1) and 2-[1-(3,5-diphenylpyrazol-1-yl)ethyl]pyridine (L2) were obtained in a three-step procedure which involved the reduction of acetylpyridine using NaBH4, chlorination of the alcohol intermediate using SOCl2 and subsequent… Click to show full abstract

Abstract Compounds 2-[1-(3,5-dimethylpyrazol-1-yl)ethyl]pyridine (L1) and 2-[1-(3,5-diphenylpyrazol-1-yl)ethyl]pyridine (L2) were obtained in a three-step procedure which involved the reduction of acetylpyridine using NaBH4, chlorination of the alcohol intermediate using SOCl2 and subsequent reaction with appropriate pyrazoles. Reactions of L1 and L2 with Ni(II) and Fe(II) halides produced the respective complexes Ni(L1)Br2 (1), Ni(L1)Cl2 (2), Fe(L1)Cl2 (3) and Ni(L2)Br2 (4) as racemic mixtures in moderate yields. The molecular structures of complexes 1 and 4 are dinuclear and mononuclear respectively. All the complexes (1–4) formed active catalysts for the transfer hydrogenation of ketones (THK) in 2-propanol at 82 °C affording conversions of 58%–84% within 48 h. The influence of catalyst structure, reaction conditions and identity of ketone substrates in the TH reactions have been successfully established.

Keywords: orientation towards; pyridine; transfer hydrogenation; ethyl pyridine; hydrogenation ketones

Journal Title: Journal of Molecular Structure
Year Published: 2017

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