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

被引：65

作者：

Baan, Zoltan ^{[1
,2
]}

Finta, Zoltan ^{[1
]}

Keglevich, Gyoergy ^{[2
]}

Hermecz, Istvan ^{[1
]}

机构：

[1] Chinoin Ltd, H-1045 Budapest, Hungary

[2] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1111 Budapest, Hungary

来源：

GREEN CHEMISTRY | 2009年 / 11卷 / 12期

关键词：

REDUCTION; ALKENES;

D O I：

10.1039/b913305d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chalcone and some other alpha,beta-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.

引用

页码：1937 / 1940

页数：4

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