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

Zhi-Guang Zhang, Benjamin A. Haag, Jin-Shan Li, Paul Knochel*

*Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus F, 81377 Munich, Germany, Email:

Z.-G. Zhang, B. A. Haag, J.-S. Li, P. Knochel, Synthesis, 2011, 23-29.

DOI: 10.1055/s-0030-1258348


Functionalized organozinc reagents readily react regioselectively with various aryldiazonium salts to yield 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.

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Key Words

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

ID: J66-Y2011-0000