Issue 14, 2010
From the journal:

Organic & Biomolecular Chemistry

Palladium on carbon-catalyzed synthesis of 2- and 2,3-substituted indoles under heterogeneous conditions†

Yasunari Monguchi,a   Shigeki Mori,a   Satoka Aoyagi,a   Azusa Tsutsui,a   Tomohiro Maegawaab  and  Hironao Sajiki*a  

* Corresponding authors

a Laboratory of Organic Chemistry, Department of Organic and Medicinal Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan

b Current address: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan

Abstract

A mild, efficient and LiCl-free synthetic method for indole derivatives based on the heteroannulation of alkynes with 2-iodoanilines was achieved using palladium on carbon (Pd/C) and NaOAc in heated NMP. The N-tosyl protection of 2-iodoaniline expedited the reaction progress, while other protecting groups, such as tert-butoxycarbonyl, acetyl, and benzyloxycarbonyl groups, underwent deprotection under the present conditions. A variety of di- and monosubstituted alkynes could effectively react with N-tosyl-2-iodoaniline to give the corresponding indoles in good to high yields.

Graphical abstract: Palladium on carbon-catalyzed synthesis of 2- and 2,3-substituted indoles under heterogeneous conditions

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Article information

DOI
https://doi.org/10.1039/C004939E
Article type
Paper
Submitted
07 Apr 2010
Accepted
18 May 2010
First published
04 Jun 2010

Org. Biomol. Chem., 2010,8, 3338-3342

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Palladium on carbon-catalyzed synthesis of 2- and 2,3-substituted indoles under heterogeneous conditions

Y. Monguchi, S. Mori, S. Aoyagi, A. Tsutsui, T. Maegawa and H. Sajiki, Org. Biomol. Chem., 2010, 8, 3338 DOI: 10.1039/C004939E

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