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使用[bmim]PF6/H2O体系将硫醇共轭加成到α,β-不饱和酮的绿色协议。

Green protocol for conjugate addition of thiols to alpha,beta-unsaturated ketones using a [bmim]PF6/H2O system.

作者信息

Yadav J S, Reddy B V S, Baishya Gakul

机构信息

Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500 007, India.

出版信息

J Org Chem. 2003 Sep 5;68(18):7098-100. doi: 10.1021/jo034335l.

Abstract

Alpha,beta-unsaturated ketones undergo conjugate addition rapidly with thiols in a hydrophobic ionic liquid [bmim]PF(6)/H(2)O solvent system (2:1) in the absence of any acid catalyst to afford the corresponding Michael adducts in high to quantitative yields with excellent 1,4-selectivity under mild and neutral conditions. The enones show enhanced reactivity in ionic liquids, thereby reducing reaction times and improving the yields significantly. The use of ionic liquids helps to avoid the use of either acid or base catalysts for this conversion. The recovered ionic liquid was reused four to five times with consistent activity.

摘要

在疏水性离子液体[bmim]PF₆/H₂O溶剂体系(2:1)中,α,β-不饱和酮在无任何酸催化剂的情况下能与硫醇迅速发生共轭加成反应,在温和中性条件下以高至定量的产率得到相应的迈克尔加成产物,且具有出色的1,4-选择性。烯酮在离子液体中显示出增强的反应活性,从而显著缩短反应时间并提高产率。离子液体的使用有助于避免在此转化过程中使用酸或碱催化剂。回收的离子液体可重复使用四至五次,活性保持一致。

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