NH 4 I-Promoted and H 2 O-Controlled Intermolecular Bis-sulfenylation and Hydroxysulfenylation of Alkenes via a Radical Process

作者：Runfa He, Xiuwen Chen, Yibiao Li, Qiang Liu, Chunshu Liao, Lu Chen, Yubing Huang · 发表于：The Journal of Organic Chemistry · 年份：2019 · DOI：10.1021/acs.joc.9b01047 · 被引用次数：36 · 研究领域：Sulfur-Based Synthesis Techniques、Chemical Synthesis and Reactions、Organoselenium and organotellurium chemistry

An NH 4 I-promoted and H 2 O-controlled intermolecular difunctionalization of alkenes for the synthesis of bis-methylsulfane and β-hydroxysulfides is presented. Mechanistic investigation revealed the reaction proceeds via methylthiyl radical addition to C═C of alkenes to give a carbon-centered radical and immediately cyclize to a thiiranium ion, followed by combination with H 2 O to afford β-hydroxysulfides in 52–89% yields with chemo- and regioselectivities. In the absence of water, 1,2-disulfenylation takes place to give bis-methylsulfane in moderate to good yields.