Issue 80, 2012
From the journal:

Chemical Communications

An efficient synthesis of 2-bromo(chloro)-3-selenyl(sulfenyl)indoles via tandem reactions of 2-(gem-dibromo(chloro)vinyl)anilines with diselenides(disulfides)†

Jie Liu,ab   Pinhua Li,b   Wei Chenb  and  Lei Wang*abc  

* Corresponding authors

a College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123, P R China

b Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P R China
E-mail: leiwang@chnu.edu.cn
Fax: +86 561 309 0518
Tel: +86 561 380 2069

c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P R China

Abstract

A novel and efficient synthesis of 2-bromo(chloro)-3-selenyl(sulfenyl)indoles through tandem reactions of 2-(gem-dibromo(chloro)vinyl)-N-methylsulfonylanilines with diselenides and disulfides in the presence of t-BuOLi and I2 (10 mol%) in DMSO was developed. The reactions generated the desired products in good yields with high regio-selectivity under transition-metal-free conditions in one-pot.

Graphical abstract: An efficient synthesis of 2-bromo(chloro)-3-selenyl(sulfenyl)indoles via tandem reactions of 2-(gem-dibromo(chloro)vinyl)anilines with diselenides(disulfides)

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Article information

DOI
https://doi.org/10.1039/C2CC34800D
Article type
Communication
Submitted
05 Jul 2012
Accepted
23 Aug 2012
First published
24 Aug 2012

Chem. Commun., 2012,48, 10052-10054

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An efficient synthesis of 2-bromo(chloro)-3-selenyl(sulfenyl)indoles via tandem reactions of 2-(gem-dibromo(chloro)vinyl)anilines with diselenides(disulfides)

J. Liu, P. Li, W. Chen and L. Wang, Chem. Commun., 2012, 48, 10052 DOI: 10.1039/C2CC34800D

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