Aerobic Copper(II)-catalyzed synthesis of β-hydroxysulfides and selenides from alkenes with disulfides and diselenides

A copper-catalyzed hydroxysulfenylation of alkenes was achieved using disulfides in the presence of n-Bu4NI and H2O. The procedure smoothly proceeded under air atmosphere, and the corresponding β-hydroxysulfides were obtained with regio- and anti-selectivity in good yields. Furthermore, a reaction u...

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Bibliographic Details
Published in:Tetrahedron 2022-03, Vol.110, p.132689, Article 132689
Main Author: Taniguchi, Nobukazu
Format: Article
Language:English
Subjects:
Alkenes
Copper-catalyst
Diselenides
Disulfides
Hydroxychalcogenation
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Summary:A copper-catalyzed hydroxysulfenylation of alkenes was achieved using disulfides in the presence of n-Bu4NI and H2O. The procedure smoothly proceeded under air atmosphere, and the corresponding β-hydroxysulfides were obtained with regio- and anti-selectivity in good yields. Furthermore, a reaction using diselenides effectively produced the expected β-hydroxyselenides. These reactions could use both chalcogenide groups on dichalcogenides. Further the procedure also worked for hydrosulfenylation using thiols. A copper-catalyzed hydroxychalcogenation of alkenes was achieved using dichalcogenides in the presence of n-Bu4NI and H2O under air atmosphere, and the corresponding β-hydroxychalcogenides were obtained with regio- and anti-selectivity in good yields. The procedure could use both chalcogenide groups on dichalcogenides. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2022.132689