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Synlett 2000; 2000(3): 394-396
DOI: 10.1055/s-2000-6529
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The Palladium-Catalyzed Reaction of o-Alkynyltrifluoroacetanilides with Alkyl Halides. An Entry into 2-Substituted 3-Alkylindoles

Antonio Arcadi* , Sandro Cacchi, Giancarlo Fabrizi, Fabio Marinelli
  • *Dipartimento di Chimica, Ingegneria Chimica e Materiali della Facoltà di Scienze, Università de L'Aquila, Via Vetoio, Coppito Due, I-67100 L'Aquila, Italy; Fax +39-06-49 91 27 80; E-mail: cacchi@uniroma1.it
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Publication Date:
31 December 2000 (online)

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Indolylcarboxylate esters 2 and 2-substituted 3-benzylindoles 4 are prepared usually in good yield through the palladium-catalyzed reaction of o-alkynyltrifluoro acetanilides with ethyl iodoacetate or benzyl bromide. Best results are obtained by employing Pd2(dba)3 and tris(2,4,6-trimethoxyphenyl)phosphine in THF.

3-alkylindoles - alkynes - cyclization - palladium - alkyl halides