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

doi:10.6023/cjoc201912039

Abstract

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

Cite this article

Jiang Xiaoying, Yao Chuansheng, Tong Chuo, Bai Renren, Zhou Tao, Xie Yuanyuan. Selective Oxidation of Sulfides/Disulfides to Sulfoxides/ Thiosulfonates Using t-Butyl Hydroperoxide (TBHP) without Catalyst[J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1752-1759.

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无催化条件下采用叔丁基过氧化氢(TBHP)选择性氧化硫醚/二硫醚至亚砜/单砜