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Gold(III)-Catalyzed Annulation of 2-Alkynylanilines: A Mild and Efficient Synthesis of Indoles and 3-Haloindoles

Antonio Arcadi, Gabriele Bianchi, Fabio Marinelli*

*Dipartimento di Chimica, Ingegneria Chimica e Materiali, FacoltÓ di Scienze, via Vetoio, 67100 L’Aquila, Italy, Email: fmarinelunivaq.it

A. Arcadi, G. Bianchi, F. Marinelli, Synthesis, 2004, 610-618.

DOI: 10.1055/s-2004-815947


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Abstract

Gold(III)-catalyzed annulation of 2-alkynylanilines in EtOH or EtOH-water mixtures at room temperature gives indoles derivatives in good yields. One-flask protocol for the gold-catalyzed conversion of 2-alkynylanilines to 3-bromo and 3-iodoindoles is also reported.

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Key Words

2-alkynylanilines, indoles, 5-endo-dig cyclization, gold catalysis, halogenations


ID: J66-Y2004-2000