Transition metal-free formal hydro/deuteromethylthiolation of unactivated alkenes

Methylthioether is involved in the methylthiotransfer process in organisms, and therefore its functionality is of paramount importance to living organisms. Several methods for the installation of the methylthio group in small molecules have been reported previously; however, procedures starting from...

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Published inOrganic & biomolecular chemistry Vol. 19; no. 18; pp. 437 - 442
Main Authors Chen, Shuangyang, Wang, Jia, Xie, Lan-Gui
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 12.05.2021
Royal Society of Chemistry
Subjects
Alkenes
Chemistry
Chemistry, Organic
Deuterium
Methanethiol
Physical Sciences
Science & Technology
Stimulators
Transition metals
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Summary:Methylthioether is involved in the methylthiotransfer process in organisms, and therefore its functionality is of paramount importance to living organisms. Several methods for the installation of the methylthio group in small molecules have been reported previously; however, procedures starting from unactivated alkenes are rare. Herein, we report a formal hydro/deuteromethylthiolation of alkenes by using dimethyl(methylthio)sulfonium trifluoromethanesulfonate as the stimulator and sodium borohydride/deuteride as the hydrogen/deuterium source. The process represents a mild, transition metal-free and methanethiol-free route towards the synthesis of methylthioethers from unactivated alkenes. A transition metal-free and methanethiol-free formal hydro/deuteromethylthiolation of unactivated alkenes has been developed.
Bibliography:Electronic supplementary information (ESI) available. See DOI
10.1039/d1ob00413a
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ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob00413a