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Issue 34, 2016
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Nickel-catalyzed transfer hydrogenation of ketones using ethanol as a solvent and a hydrogen donor

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Abstract

We report a nickel(0)-catalyzed direct transfer hydrogenation (TH) of a variety of alkyl–aryl, diaryl, and aliphatic ketones with ethanol. This protocol implies a reaction in which a primary alcohol serves as a hydrogen atom source and solvent in a one-pot reaction without any added base. The catalytic activity of the nickel complex [(dcype)Ni(COD)] (e) (dcype: 1,2-bis(dicyclohexyl-phosphine)ethane, COD: 1,5-cyclooctadiene), towards transfer hydrogenation (TH) of carbonyl compounds using ethanol as the hydrogen donor was assessed using a broad scope of ketones, giving excellent results (up to 99% yield) compared to other homogeneous phosphine–nickel catalysts. Control experiments and a mercury poisoning experiment support a homogeneous catalytic system; the yield of the secondary alcohols formed in the TH reaction was monitored by gas chromatography (GC) and NMR spectroscopy.

Graphical abstract: Nickel-catalyzed transfer hydrogenation of ketones using ethanol as a solvent and a hydrogen donor

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Publication details

The article was received on 10 Jul 2016, accepted on 01 Aug 2016 and first published on 02 Aug 2016


Article type: Paper
DOI: 10.1039/C6DT02725C
Citation: Dalton Trans., 2016,45, 13604-13614

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    Nickel-catalyzed transfer hydrogenation of ketones using ethanol as a solvent and a hydrogen donor

    N. Castellanos-Blanco, A. Arévalo and J. J. García, Dalton Trans., 2016, 45, 13604
    DOI: 10.1039/C6DT02725C

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