Issue 10, 2014
From the journal:

Organic Chemistry Frontiers

Brønsted acid-catalyzed synthesis of carbazoles from 2-substituted indoles†‡

Qingjiang Li,a   Xiao-Shui Pengab  and  Henry N. C. Wong*ab  

* Corresponding authors

a Department of Chemistry, Centre of Novel Functional Molecules and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China

b Shenzhen Municipal Key Laboratory of Chemical Synthesis of Medicinal Organic Molecules and Shenzhen Center of Novel Functional Molecules, Shenzhen Research Institute, The Chinese University of Hong Kong, No. 10. Second Yuexing Road, Shenzhen 518507, China
E-mail: hncwong@cuhk.edu.hk
Fax: +852 26035315

Abstract

A simple and efficient method for the synthesis of disubstituted carbazoles has been developed. In this approach, carbazoles are synthesized from o-haloanilines and terminal alkynes using a two-step strategy, namely, Sonogashira coupling and intramolecular cyclization to provide indoles, which are followed by a p-TSA·H2O-catalyzed carbazole formation.

Graphical abstract: Brønsted acid-catalyzed synthesis of carbazoles from 2-substituted indoles

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Article information

DOI
https://doi.org/10.1039/C4QO00242C
Article type
Research Article
Submitted
05 Sep 2014
Accepted
03 Oct 2014
First published
06 Oct 2014

Org. Chem. Front., 2014,1, 1197-1200

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Brønsted acid-catalyzed synthesis of carbazoles from 2-substituted indoles

Q. Li, X. Peng and H. N. C. Wong, Org. Chem. Front., 2014, 1, 1197 DOI: 10.1039/C4QO00242C

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