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NH4I-Promoted and H2O-Controlled Intermolecular Bis-sulfenylation and Hydroxysulfenylation of Alkenes via a Radical Process

Runfa He, Xiuwen Chen, Yibiao Li*, Qiang Liu, Chunshu Liao, Lu Chen, Yubing Huang

*School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529090, China, Email:

R. He, X. Chen, Y. Li, Q. Liu, C. Liao, L. Chen, Y. Huang, J. Org. Chem., 2019, 84, 8750-8758.

DOI: 10.1021/acs.joc.9b01047

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An NH4I-promoted and H2O-controlled intermolecular difunctionalization of alkenes provides bis-methylsulfanes and β-hydroxysulfides via methylthiyl radical addition to the double bond to give a carbon-centered radical, which immediately cyclizes to a thiiranium ion, followed by combination with H2O to afford β-hydroxysulfides. In the absence of water, 1,2-disulfenylation takes place.

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proposed mechanism

Key Words

hydroxylation, sulfenylation

ID: J42-Y2019