Elemental sulfur as a sulfuration agent in the copper-catalyzed C–H bond thiolation of electron-deficient arenes,Organic & Biomolecular Chemistry

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Elemental sulfur as a sulfuration agent in the copper-catalyzed C–H bond thiolation of electron-deficient arenes
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2017-09-13 00:00:00 , DOI: 10.1039/c7ob02036h
Haiming Yan _{1,

2,

3,

4} , Zhiliang Huang _{5,

6,

7,

8,

9} , Meng Chen _{1,

2,

3,

4} , Cuiting Li _{1,

2,

3,

4} , Ya Chen _{1,

2,

3,

4} , Meng Gao _{1,

2,

3,

4} , Aiwen Lei _{1,

2,

3,

4,

5}

Affiliation

By utilizing elemental sulfur as the thiolation agent and oxidant, a copper-catalyzed direct C–H bond thiolation of electron-deficient arenes was demonstrated. Various electron-deficient arenes were proved to be suitable for this transformation. Preliminary mechanistic studies indicated that this reaction underwent a radical pathway, in which the trisulfur radical anion (S₃˙⁻) might play a vital role. Meanwhile, KIE experiments suggested that C–H bond cleavage was not involved in the rate-determining step.

中文翻译：

铜在电子缺陷型芳烃的铜催化的CH键硫醇化中作为硫化剂的元素硫

通过利用元素硫作为硫醇化剂和氧化剂，对缺电子的芳烃进行了铜催化的直接C–H键硫醇化反应。各种缺乏电子的芳烃被证明适用于这种转变。初步机理研究表明，该反应经历了一个激进的途径，其中trisulfur阴离子自由基（S ₃ ˙ ^-）可能会发挥重要的作用。同时，KIE实验表明，CH键的断裂不参与速率确定步骤。

更新日期：2017-09-22

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