Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1752-1759.DOI: 10.6023/cjoc201912039 Previous Articles     Next Articles


蒋筱莹a, 姚传胜b, 童踔b, 白仁仁b, 周涛c, 谢媛媛a,b   

  1. a 浙江工业大学 长三角绿色制药协同创新中心 杭州 310014;
    b 浙江工业大学药学院 杭州 310014;
    c 浙江工商大学食品科学与生物技术学院 杭州 310018
  • 收稿日期:2019-12-26 修回日期:2020-03-10 发布日期:2020-03-31
  • 通讯作者: 谢媛媛
  • 基金资助:

Selective Oxidation of Sulfides/Disulfides to Sulfoxides/ Thiosulfonates Using t-Butyl Hydroperoxide (TBHP) without Catalyst

Jiang Xiaoyinga, Yao Chuanshengb, Tong Chuob, Bai Renrenb, Zhou Taoc, Xie Yuanyuana,b   

  1. a Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceutical, Zhejiang University of Technology, Hangzhou 310014;
    b College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014;
    c School of Food Science and Biotechnology, Zhejiang Gongshang University, Hangzhou 310018
  • Received:2019-12-26 Revised:2020-03-10 Published:2020-03-31
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21576239).

A novel and simple method for the selectively oxidation of sulfides to sulfoxides and oxidation of disulfides to thiosulfonates in the presence of t-butyl hydroperoxide (TBHP) has been established. The oxidation system has the advantages of avoiding the use of any catalyst and additive, possessing a broad substrate scope and high efficiency. Desired sulfoxides and thiosulfonates products were obtained in moderate to good yields. Furthermore, a plausible mechanism of the reaction is proposed. The results of control experiments revealed that a radical pathway was involved in this oxidation.

Key words: sulfides/disulfides, sulfoxides/thiosulfonates, t-butylhydroperoxide, oxidation, catalyst/additive free