Issue 24, 2018

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
22 Aug 2018
Accepted
17 Oct 2018
First published
08 Nov 2018

Org. Chem. Front., 2018,5, 3557-3561

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, 5, 3557 DOI: 10.1039/C8QO00909K

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