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From Alcohols to Indoles: A Tandem Ru Catalyzed Hydrogen-Transfer Fischer Indole Synthesis

Andrea Porcheddu*, Manuel G. Mura, Lidia De Luca, Marianna Pizzetti and Maurizio Taddei

*Dipartimento di Chimica e Farmacia, UniversitÓ degli Studi di Sassari, via Vienna 2, 07100 Sassari, Italy, Email: anpouniss.it

A. Porcheddu, M. G. Mura, L. De Luca, M. Pizzetti, M. Taddei, Org. Lett., 2012, 14, 6112-6115.

DOI: 10.1021/ol3030956 (free Supporting Information)


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Abstract

In a new version of the Fischer indole synthesis, primary and secondary alcohols have been catalytically oxidized in the presence of phenylhydrazines and Lewis acids to give the corresponding indoles in one step. The use of alcohols instead of aldehydes or ketones broadens the scope of available starting materials and offers easy handling and safety.

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Key Words

Fischer Indole Synthesis, Indoles, Crotononitrile, Microwave Synthesis


ID: J54-Y2012-3810