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Synthesis 2011(1): 23-29  
DOI: 10.1055/s-0030-1258348
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© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Preparation of Polyfunctional Indoles via a Zinc Organometallic Variation of the Fischer Indole Synthesis

Zhi-Guang Zhanga,b, Benjamin A. Haaga, Jin-Shan Lib, Paul Knochel*a
a Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus F, 81377 Munich, Germany
Fax: +49(89)218077680; e-Mail: paul.knochel@cup.uni-muenchen.de;
b State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China
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Publication History

Received 28 October 2010
Publication Date:
03 December 2010 (online)

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Abstract

Functionalized organozinc reagents readily react with various aryldiazonium salts furnishing regioselectively polyfunctional indoles after heating with microwave irradiation. This new organometallic variation of the Fischer indole synthesis tolerates a wide range of functional groups and can be readily scaled up.

Key words

organozinc reagents - indoles - regioselectivity - Fischer indole synthesis - N-heterocycles

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