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Acid-catalyzed oxidative cleavage of S–S and Se–Se bonds with DEAD: efficient access to sulfides and selenides

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Abstract

An acid/DEAD system for efficient oxidative cleavage of S–S and Se–Se bonds to generate chalcogenium ions has been developed. These ions could be captured by nucleophile-tethered alkenes and nucleophilic aryl reagents such as arylboronic acids and arenes to afford diverse chalcogenides. Mechanistic studies revealed that an N-sulfenylhydrazine intermediate was involved in the transformations.

Graphical abstract: Acid-catalyzed oxidative cleavage of S–S and Se–Se bonds with DEAD: efficient access to sulfides and selenides

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Publication details

The article was received on 22 Aug 2018, accepted on 17 Oct 2018 and first published on 08 Nov 2018


Article type: Research Article
DOI: 10.1039/C8QO00909K
Citation: Org. Chem. Front., 2018, Advance Article
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    Acid-catalyzed oxidative cleavage of S–S and Se–Se bonds with DEAD: efficient access to sulfides and selenides

    R. An, L. Liao, X. Liu, S. Song and X. Zhao, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00909K

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