Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides. Issue 12 (7th March 2017)

• Record Type: Journal Article
• Authors: Gan, Shaoyan; Yin, Junjie; Yao, Yuan; Liu, Yang; Chang, Denghu; Zhu, Dan; Shi, Lei
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 12(2017)
• Page Start: 2647
• Page End: 2654
• Publication Date: 2017-03-07
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob00021a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Metal- and additive-free sulfoxidation was developed using cyclic diacyl peroxides as oxygen sources and a single two-electron transfer mechanism was suggested. Abstract : Metal- and additive-free oxidation of a series of sulfides/thioketones has been achieved using cyclic diacyl peroxides as mild oxygen sources. This protocol features simple manipulation, high chemo- and diastereoselectivity, and a broad substrate scope (up to 42 examples), tolerates many common functional groups, and is scalable and applicable to the late-stage sulfoxidation strategy. A preliminary mechanistic study by quantum mechanical calculations suggests that a single two-electron transfer process is energetically more favorable, and indicates the reactivity of cyclic diacyl peroxides distinct from conventional acyclic acyl peroxides.