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J Org Chem. 2019 Jul 5;84(13):8750-8758. doi: 10.1021/acs.joc.9b01047. Epub 2019 Jun 24.

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

Author information

1
School of Biotechnology and Health Sciences , Wuyi University , Jiangmen , Guangdong 529090 , China.
2
Center of Basic Molecular Science, Department of Chemistry , Tsinghua University , Beijing 100084 , China.

Abstract

An NH4I-promoted and H2O-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 H2O 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.

PMID:
31185173
DOI:
10.1021/acs.joc.9b01047

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