Synthesis of 2‐Aryl‐2‐hydroxyethyl Dithiocarbamates via Regioselective Addition of Tetraalkylthiuram Disulfides to Styrenes under Transition‐Metal‐Free Conditions,Advanced Synthesis & Catalysis

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Synthesis of 2‐Aryl‐2‐hydroxyethyl Dithiocarbamates via Regioselective Addition of Tetraalkylthiuram Disulfides to Styrenes under Transition‐Metal‐Free Conditions
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-09-10 , DOI: 10.1002/adsc.202000729
Shuai Hao ₁ , Xiefeng Ye ₁ , Mingqin Zhao ₁ , Jingyan Hu ₁ , Na Wang ₂ , Jing Li ₁ , Fangling Wang ₁ , Mingyue Zhang ₁ , Zhiyong Wu ₁

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This paper describes a method for the synthesis of 2‐aryl‐2‐hydroxyethyl dithiocarbamates via difunctionalization of alkenes involving C−S and C−O bonds formation with tetraalkylthiuram disulfides as the functional reagents. The reaction proceeded well under transition‐metal‐free conditions and afforded up to 88% yield of the desired products. Numerous useful functional groups were tolerated under the reaction conditions. This methodology provides a direct approach to β‐hydroxy dithiocarbamates, featuring readily available starting materials and broad substrate scope, which shows its practical synthetic value in organic synthesis.

中文翻译：

在无过渡金属条件下通过四烷基秋兰姆二硫化物向苯乙烯的区域选择性加成合成2-芳基-2-羟乙基二硫代氨基甲酸酯

本文描述了一种通过以二烷基四硫代秋兰姆为功能试剂的涉及C-S和C-O键形成的烯烃双官能化反应来合成2-芳基-2-羟乙基二硫代氨基甲酸酯的方法。该反应在无过渡金属的条件下进行得很好，并提供了高达88％的所需产物收率。在反应条件下容许许多有用的官能团。这种方法为β-羟基二硫代氨基甲酸酯提供了一种直接方法，其特点是容易获得的起始原料和广泛的底物范围，这表明了其在有机合成中的实用合成价值。

更新日期：2020-11-19

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