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在多相催化下甘油中的高效合成方案。

Efficient synthetic protocols in glycerol under heterogeneous catalysis.

机构信息

Dipartimento di Scienza e Tecnologia del Farmaco, Università degli Studi di Torino, Via P. Giuria 9, 10125 Torino, Italy.

出版信息

ChemSusChem. 2011 Aug 22;4(8):1130-4. doi: 10.1002/cssc.201100106. Epub 2011 Aug 18.

Abstract

The massive increase in glycerol production from the transesterification of vegetable oils has stimulated a large effort to find novel uses for this compound. Hence, the use of glycerol as a solvent for organic synthesis has drawn particular interest. Drawbacks of this green and renewable solvent are a low solubility of highly hydrophobic molecules and a high viscosity, which often requires the use of a fluidifying co-solvent. These limitations can be easily overcome by performing reactions under high-intensity ultrasound and microwaves in a stand-alone or combined manner. These non-conventional techniques facilitate and widen the use of glycerol as a solvent in organic synthesis. Glycerol allows excellent acoustic cavitation even at high temperatures (70-100 °C), which is otherwise negligible in water. Herein, we describe three different types of applications: 1) the catalytic transfer hydrogenation of benzaldehyde to benzyl alcohol in which glycerol plays the dual role of the solvent and hydrogen donor; 2) the palladium-catalyzed Suzuki cross-coupling; and (3) the Barbier reaction. In all cases glycerol proved to be a greener, less expensive, and safer alternative to the classic volatile organic solvents.

摘要

从植物油的酯交换反应中大量生产甘油,刺激了人们寻找这种化合物新用途的巨大努力。因此,甘油作为有机合成的溶剂引起了特别的关注。这种绿色可再生溶剂的缺点是对高疏水分子的溶解度低,粘度高,这通常需要使用流动性共溶剂。通过以独立或组合的方式在高强度超声和微波下进行反应,可以很容易地克服这些限制。这些非常规技术促进并拓宽了甘油在有机合成中的溶剂用途。甘油即使在高温(70-100°C)下也能产生出色的声空化,而在水中则可以忽略不计。在此,我们描述了三种不同类型的应用:1)在甘油中,苯甲醛的催化转移氢化反应同时充当溶剂和氢供体;2)钯催化的 Suzuki 交叉偶联反应;3)Barbier 反应。在所有情况下,甘油都被证明是一种更环保、更经济、更安全的替代经典挥发性有机溶剂的选择。

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