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2020 , Vol. 40 >Issue 8: 2433 - 2441

DOI: https://doi.org/10.6023/cjoc202001007

研究论文

高价碘试剂促进的N-芳基磺酰胺类化合物脱芳基反应

  • 宋蒙蒙 ,
  • 张志国 ,
  • 郑丹 ,
  • 李祥 ,
  • 梁蕊 ,
  • 赵旭娜 ,
  • 时蕾 ,
  • 张贵生
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  • a 河南师范大学化学化工学院 河南新乡 453007;
    b 许昌市质量技术监督检验测试中心 河南许昌 461000

收稿日期: 2020-01-04

  修回日期: 2020-05-16

  网络出版日期: 2020-05-28

基金资助

国家自然科学基金（Nos.U1604285，21772032，21702051）、长江学者和创新团队发展计划（No.IRT1061）、工业过程智能控制创新引智基地（No.D17007）和河南省教育厅重点（No.18A150009）资助项目.

收起

Hypervalent Organoiodine Promoted Dearylation Reaction of N-Aryl Sulfonamides

  • Song Mengmeng ,
  • Zhang Zhiguo ,
  • Zheng Dan ,
  • Li Xiang ,
  • Liang Rui ,
  • Zhao Xu'na ,
  • Shi Lei ,
  • Zhang Guisheng
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  • a School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007;
    b Quality and Technique Supervision, Inspection and Testing Center of Xuchang City, Xuchang, Henan 461000

Received date: 2020-01-04

  Revised date: 2020-05-16

  Online published: 2020-05-28

Supported by

Project supported by the National Natural Science Foundation of China (Nos. U1604285, 21772032, 21702051), Program for Changjiang Scholars and Innovative Research Team in University (No. IRT1061), Industrial Process Intelligent Control Innovation and Talent Recruitment Base (No. D17007) and the Key Project of Henan Educational Committee (No. 18A150009).

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摘要

通过高选择性惰性磺酰胺芳基C—N键裂解反应，发展了一种Dess-Martin氧化剂（DMP）促进的N-芳基磺酰胺的脱芳基的方法.该无金属参与的反应在温和的条件下进行，可提供各种在生物学上有重要应用价值的伯磺酰胺类化合物，其中某些磺酰胺使用传统的氨解和水解方法难以获得.这一简单有效的脱芳基反应可在无金属催化剂条件下使芳基作为磺酰胺类化合物的氨基保护基.

关键词： 戴斯马丁氧化剂; 芳基C-N键断裂; 氧化反应; 无金属反应; 磺酰胺

本文引用格式

宋蒙蒙 , 张志国 , 郑丹 , 李祥 , 梁蕊 , 赵旭娜 , 时蕾 , 张贵生 . 高价碘试剂促进的N-芳基磺酰胺类化合物脱芳基反应[J]. 有机化学, 2020 , 40(8) : 2433 -2441 . DOI: 10.6023/cjoc202001007

Abstract

An efficient Dess-Martin periodinane (DMP)-promoted dearylation of N-arylsulfonamides was developed through a highly selective oxidative cleavage of the inert C(aryl)-N bonds in secondary sulfonamides while leaving the S-N bond unchanged. This metal-free reaction proceeds under mild conditions and provides access to various biologically important primary sulfonamides, some of which are otherwise unattainable using conventional aminolysis and hydrolysis methods. The concise and efficient dearylation reaction provides the use of an aryl group as a removable protecting sulfonamide group under metal catalyst-free conditions.

Key words： Dess-Martin periodinane (DMP); C(aryl)-N bond cleavage; oxidation; metal-free reaction; sulfonamide

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