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Palladium-catalyzed reaction of aryl iodides with tertiary propargylic amides.: Highly substituted allenes through a regioselective carbopalladation/β-NPd elimination reaction
Authors:Antonio Arcadi  Giancarlo Fabrizi  Luca M Parisi
Institution:a Dipartimento di Chimica Ingegneria Chimica e Materiali della Facoltà di Scienze, Università di L'Aquila, Via Vetoio, Coppito Due, I-67100 L'Aquila, Italy
b Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università degli Studi “La Sapienza”, P.le A. Moro 5, 00185 Rome, Italy
Abstract:The palladium-catalyzed reaction of aryl iodides with tertiary propargylic amides affords highly substituted allenes. Best results have been obtained by using Pd(OAc)2, nBu3N, HCOOH, and nBu4NCl or LiCl in DME at 100 °C. The reaction is highly regioselective and the carbopalladation step is controlled by the strong directing effect of the tertiary amide group.
Keywords:Palladium  Allenes  Hydroarylation  Alkynes
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