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铜催化的 NH-亚磺酰胺与芳基重氮四氟硼酸盐和二氧化硫的磺酰化反应:-磺酰基亚磺酰胺的形成。

Copper-Catalyzed Sulfonylation Reaction of NH-Sulfoximines with Aryldiazonium Tetrafluoroborates and Sulfur Dioxide: Formation of -Sulfonyl Sulfoximines.

机构信息

Guangxi Key Laboratory of Electrochemical and Magnetochemical Function Materials, College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, People's Republic of China.

出版信息

J Org Chem. 2023 Feb 17;88(4):2322-2333. doi: 10.1021/acs.joc.2c02742. Epub 2023 Jan 26.

Abstract

An efficient and practical SO insertion protocol of NH-sulfoximines with aryldiazonium tetrafluoroborates and DABSO toward -sulfonyl sulfoximines has been developed under mildly basic conditions. This transformation features easy operation, readily available substrates, and mild conditions. A tentative mechanism is proposed, which indicates that the aryldiazonium tetrafluoroborates would be radical donors under standard reaction conditions. The aryl radical produced in situ from diazonium salts would be trapped by SO to generate an arylsulfonyl radical and then undergo further transformation to generate the final -sulfonyl sulfoximines.

摘要

在温和的碱性条件下,开发了一种高效实用的 NH-亚磺酰胺与芳基重氮四氟硼酸盐和 DABSO 向 -磺酰基亚磺酰胺的 SO 插入协议。该转化具有操作简单、底物易得、条件温和等特点。提出了一个推测的反应机理,表明芳基重氮四氟硼酸盐在标准反应条件下是自由基供体。芳基自由基是由重氮盐原位生成的,它会被 SO 捕获生成芳基磺酰基自由基,然后进一步转化生成最终的 -磺酰基亚磺酰胺。

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