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Synthesis 2004(11): 1889-1894  
DOI: 10.1055/s-2004-815993
PSP
© Georg Thieme Verlag Stuttgart · New York

Preparation of Indoles from o -Alkynyltrifluoroacetanilides Through the Aminopalladation­-Reductive Elimination Process

Sandro Cacchi*, Giancarlo Fabrizi, Luca M. Parisi
Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università degli Studi ‘La Sapienza’, P. le A. Moro 5, 00185 Roma, Italy
Fax: +39(6)49912780; e-Mail: sandro.cacchi@uniroma1.it;
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Publication History

Received 22 December 2003
Publication Date:
03 March 2004 (online)

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Abstract

The functionalized pyrrole nucleus contained in the indole system has been assembled via the palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with organic halides/triflates or allyl carbonates. In the presence of carbon monoxide, a three-component reaction can take place and indole derivatives incorporating a molecule of carbon monoxide have been obtained.

Key words

indoles - alkynes - cyclization - palladium - catalysis

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5

o-Ethynyltrifluoroacetanilide can be prepared in 70% overall yield from commercially available o-iodoaniline via a three-step process as described in Ref.3