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Issue 12, 2009
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Unexpected chemoselectivity in the rhodium-catalyzed transfer hydrogenation of α,β-unsaturated ketones in ionic liquids

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Abstract

Chalcone and some other α,β-unsaturated ketones were subjected to transfer hydrogenation catalyzed by the dimer [Rh(cod)Cl]2 and the Wilkinson's catalyst in imidazolium-, ammonium- and phosphonium-based ionic liquids. In certain ionic liquids, the reduction of chalcone gave 1,3-diphenylpropan-1-one chemoselectively, in contrast with molecular solvents, which resulted in the formation of 1,3-diphenylpropan-1-ol. An accelerated reaction rate was observed in [emim][BuSO4] and [emin][HeSO4]. The observed chemoselectivity could be maintained applying a 5 molar equivalent excess of [bmim][BF4] to chalcone in 2-PrOH. This phenomenon suggests that there is an interaction between the chalcone carbonyl group and the ionic liquid which prevents reduction of the carbonyl group. The catalyst [Rh(cod)Cl]2 dissolved in an ionic liquid was successfully recycled at least three times, in contrast with Wilkinson's catalyst, which lost its activity on recycling.

Graphical abstract: Unexpected chemoselectivity in the rhodium-catalyzed transfer hydrogenation of α,β-unsaturated ketones in ionic liquids

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Publication details

The article was received on 06 Jul 2009, accepted on 16 Sep 2009 and first published on 01 Oct 2009


Article type: Communication
DOI: 10.1039/B913305D
Citation: Green Chem., 2009,11, 1937-1940
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    Unexpected chemoselectivity in the rhodium-catalyzed transfer hydrogenation of α,β-unsaturated ketones in ionic liquids

    Z. Baán, Z. Finta, G. Keglevich and I. Hermecz, Green Chem., 2009, 11, 1937
    DOI: 10.1039/B913305D

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