"On-Water" Michael-Type Addition Reactions Promoted by PhSeZnCl

被引：38

作者：

Battistelli, Benedetta ^{[1
]}

Lorenzo, Testaferri ^{[1
]}

Tiecco, Marcello ^{[1
]}

Santi, Claudio ^{[1
]}

机构：

[1] Univ Perugia, Dipartimento Chim & Tecnol Farmaco, I-06123 Perugia, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 10期

关键词：

Selenium; Zinc; Michael addition; Water chemistry; Nucleophilic addition; CONJUGATED ALKENES; HYDROSELENATION; BENZENESELENOL; CHEMISTRY; CLEAVAGE; GREEN;

D O I：

10.1002/ejoc.201100045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this communication we report that our reagent PhSeZnCl can be conveniently used to effect Michael addition like reactions of unsaturated ketones and electron-deficient alkynes, leading to synthetically useful beta-seleno derivatives and vinyl selenides, respectively. The reactions are effected at room temperature in THF as well as under "on water" conditions. When the addition occurs on a triple bond, good stereoselectivity is observed, and the reaction shows a rate acceleration in water suspension.

引用

页码：1848 / 1851

页数：4

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