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Fe(OTf)2-Catalyzed Thia-Michael Addition Reaction: A Green Synthetic Approach to beta-Thioethers
European Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2018-08-17 , DOI: 10.1002/ejoc.201800780
Samuel Lauzon 1 , Mao Li 1 , Hoda Keipour 1 , Thierry Ollevier 1
Affiliation  

A convenient Fe(OTf)2-catalyzed Michael addition reaction of thiols to α,β-unsaturated carbonyl compounds was developed. The use of a simple procedure (EtOH, room temperature, air atmosphere) allowed to set up effective green catalytic conditions for the C–S bond formation. The scope of the reaction was demonstrated using various substituted thiols and original Michael acceptors. The corresponding β-thioethers were obtained in good to excellent yields (up to 99%). Also, the derivatization into the one-pot thia-Michael addition/oxidation reaction of 3-(3-(phenylthio)butanoyl)oxazolidin-2one using H2O2 has proven to be efficient.

中文翻译:

Fe(OTf)2-催化的硫-迈克尔加成反应:β-硫醚的绿色合成方法

开发了一种方便的 Fe(OTf)2 催化的硫醇迈克尔加成反应生成 α,β-不饱和羰基化合物。使用简单的程序(乙醇、室温、空气气氛)可以为 C-S 键的形成建立有效的绿色催化条件。使用各种取代的硫醇和原始迈克尔受体证明了反应的范围。相应的 β-硫醚以良好到极好的收率(高达 99%)获得。此外,已证明使用 H2O2 将 3-(3-(苯硫基)丁酰基)恶唑烷-2one 衍生为一锅硫杂-迈克尔加成/氧化反应是有效的。
更新日期:2018-08-17
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