Nitrosoarenes as Nitrogen Source for Generation of Sulfonamides with the Insertion of Sulfur Dioxide under Metal‐Free Conditions†,Chinese Journal of Chemistry

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Nitrosoarenes as Nitrogen Source for Generation of Sulfonamides with the Insertion of Sulfur Dioxide under Metal‐Free Conditions†
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2020-05-02 , DOI: 10.1002/cjoc.202000053
Xuefeng Wang _{1,

2} , Yanmei Lin ₁ , Jin‐Biao Liu ₂ , Fu‐Sheng He ₂ , Yunyan Kuang ₁ , Jie Wu _{2,

3}

Affiliation

A metal‐free reaction of nitrosoarenes, aryldiazonium tetrafluoroborates, and sulfur dioxide under mild conditions is developed, giving rise to sulfonamides in moderate to good yields. This transformation proceeds efficiently at room temperature in the presence of cyclohexa‐1,4‐diene with a broad reaction scope. Good functional group compatibility is observed, including cyano, halo, and ester. A plausible mechanism involving a radical process with the insertion of sulfur dioxide is proposed, and cyclohexa‐1,4‐diene serves as the reductant during the transformation.

中文翻译：

在无金属条件下，以亚硝基芳烃为氮源，通过插入二氧化硫生成磺酰胺

在温和条件下开发了亚硝基芳烃，芳基重氮四氟硼酸盐和二氧化硫的无金属反应，从而以中等至良好的产率产生了磺酰胺。在具有宽反应范围的环己-1,4-二烯存在下，这种转化在室温下可有效进行。观察到良好的官能团相容性，包括氰基，卤素和酯。提出了一种可能的机制，其中涉及一个自由基过程，其中插入了二氧化硫，并且在转化过程中，环己-1,4-二烯用作还原剂。

更新日期：2020-05-02

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