Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (8): 2483-2490.DOI: 10.6023/cjoc201912045 Previous Articles     Next Articles

原位产生二氧化锰催化构建S—S键

吕进强, 曾竟, 阿布都热西提·阿布力克木   

  1. 新疆师范大学化学系 乌鲁木齐 830054
  • 收稿日期:2019-12-31 修回日期:2020-05-12 出版日期:2020-08-25 发布日期:2020-05-20
  • 通讯作者: 阿布都热西提·阿布力克木, 曾竟 E-mail:aarexit@xjnu.edu.cn;zengjing800111@163.com
  • 基金资助:
    新疆维吾尔自治区高校科研计划自然科学重点项目(No.XJEDU2020I015)和新疆维吾尔自治区2017年自治区“天山青年计划”(No.2017Q026)资助项目.

Highly Active Manganese Dioxide Catalyzed the Construction of S-S Bond

Lü Jinqiang, Zeng Jing, Abulikemu Abudu Rexit   

  1. Department of Chemistry, Xinjiang Normal University, Urumqi 830054
  • Received:2019-12-31 Revised:2020-05-12 Online:2020-08-25 Published:2020-05-20
  • Supported by:
    Project supported by the Scientific Research Program of the Higher Education Institution of Xinjiang (No. XJEDU2020I015), and the Xinjiang Tianshan Youth Program (No. 2017Q026).

Generation of highly active manganese dioxide in situ by using catalytic amount of potassium permanganate in anhydrous ethanol system, the catalytic system promoted S-S bond construction by free radical self coupling reactions of thiophenol and mercaptan compounds at room temperature. 14 disulfides were obtained with 70%~99% yields. At the same time, it was also found that the catalytic system could also catalyze radical cross-coupling reactions between symmetric disulfides and different substituents of thiophenols, thiols, or two different symmetric disulfides, 13 asymmetric disulfides were obtained with 19%~72% yields. The protocol offered the advantages of simple and efficient, easy separation, green solvent, wide range of substrate applications, and mild conditions. All products were confirmed by 1H NMR and 13C NMR spectra.

Key words: free radical coupling reaction, S-S bond, manganese dioxide