Issue 1, 2013

The facile synthesis of 2-bromoindoles via Cs2CO3-promoted intramolecular cyclization of 2-(gem-dibromovinyl)anilines under transition-metal-free conditions

Abstract

2-Bromoindoles were readily prepared through a facile Cs2CO3-promoted intramolecular cyclization of 2-(gem-bromovinyl)-N-methylsulfonylanilines in excellent yields under transition-metal-free conditions. This methodology could be extended to the synthesis of corresponding 2-chloroindoles. The reaction mechanism suggested that cyclization occurs through a key intermediate, phenylethynyl bromide, followed by cyclization in one-pot.

Graphical abstract: The facile synthesis of 2-bromoindoles via Cs2CO3-promoted intramolecular cyclization of 2-(gem-dibromovinyl)anilines under transition-metal-free conditions

Supplementary files

Article information

Article type
Communication
Submitted
15 Sep 2012
Accepted
29 Oct 2012
First published
30 Oct 2012

RSC Adv., 2013,3, 73-78

The facile synthesis of 2-bromoindoles via Cs2CO3-promoted intramolecular cyclization of 2-(gem-dibromovinyl)anilines under transition-metal-free conditions

P. Li, Y. Ji, W. Chen, X. Zhang and L. Wang, RSC Adv., 2013, 3, 73 DOI: 10.1039/C2RA22172A

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