Issue 40, 2013
From the journal:

RSC Advances

Synthesis of 2-vinyl-2H-benzotriazoles via NIS-promoted regio/stereoselective addition of 1H-benzotriazole to alkynes†

Zhenhua Zhang,a   Lina Chang,a   Shaozhong Wang,*a   Huaqin Wangb  and  Zhu-Jun Yaoa  

* Corresponding authors

a State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. China
E-mail: wangsz@nju.edu.cn

b Modern Analytical Center of Nanjing University, Nanjing 210093, P. R. China

Abstract

A regio/stereoselective electrophilic addition of 1H-benzotriazole to aromatic alkynes induced by N-iodosuccinimide (NIS) has been achieved, providing unique access to 2-vinyl-2H-benzotriazole derivatives. It was demonstrated that the stereoselectivity is controlled by the nature of the substituents attached to the alkyne terminus. A mechanism involving cyclic iodonium and vinyl cation intermediates was proposed.

Graphical abstract: Synthesis of 2-vinyl-2H-benzotriazoles via NIS-promoted regio/stereoselective addition of 1H-benzotriazole to alkynes

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C3RA43075H
Article type
Paper
Submitted
19 Jun 2013
Accepted
05 Aug 2013
First published
07 Aug 2013

RSC Adv., 2013,3, 18446-18452

Permissions

Request permissions

Synthesis of 2-vinyl-2H-benzotriazoles via NIS-promoted regio/stereoselective addition of 1H-benzotriazole to alkynes

Z. Zhang, L. Chang, S. Wang, H. Wang and Z. Yao, RSC Adv., 2013, 3, 18446 DOI: 10.1039/C3RA43075H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements