Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (8): 2433-2441.DOI: 10.6023/cjoc202001007 Previous Articles     Next Articles

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a, 张志国a, 郑丹b, 李祥a, 梁蕊a, 赵旭娜a, 时蕾a, 张贵生a   

  1. 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 出版日期:2020-08-25 发布日期:2020-05-28
  • 通讯作者: 张志国, 张贵生 E-mail:Zhangzg@htu.edu.cn;zgs6668@yahoo.com
  • 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.

Hypervalent Organoiodine Promoted Dearylation Reaction of N-Aryl Sulfonamides

Song Mengmenga, Zhang Zhiguoa, Zheng Danb, Li Xianga, Liang Ruia, Zhao Xu'naa, Shi Leia, Zhang Guishenga   

  1. 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:2020-01-04 Revised:2020-05-16 Online:2020-08-25 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).

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