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Synthesis 2003(5): 0728-0734
DOI: 10.1055/s-2003-38079
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

2-Substituted 3-Aryl- and 3-Heteroarylindoles by the Palladium-Catalyzed Reaction of o-Trifluoroacetanilides with Aryl Bromides and Triflates.

Sandro Cacchi*a, Giancarlo Fabrizia, Doriano Lambab, Fabio Marinellic, Luca M. Parisia
a Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università degli Studi ‘La Sapienza’, P.le A. Moro5, 00185 Roma, Italy.
Fax: +39(06)49912780; e-Mail: sandro.cacchi@uniroma1.it.;
b Institute of Structural Chemistry - CNR Trieste, XRD1 beamline - Elettra Trieste, Italy.
c Dipartimento di Chimica Ingegneria Chimica e Materiali della Facoltà di Scienze, Università di L’Aquila, Via Vetoio, Coppito Due, 67100 L’Aquila, Italy.
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Publication History

Received 27 January 2003
Publication Date:
21 March 2003 (online)

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Abstract

The palladium-catalyzed reaction of aryl and heteroaryl bromides and triflates with o-alkynyltrifluoroacetanilides affords 2-substituted 3-aryl- and heteroarylindoles usually in excellent yield. The procedure can be applied to the synthesis of 2-substituted indole-3-carboxaldehydes.

Key words

palladium - alkynes - indoles - aryl halides - cyclization

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