Palladium-catalyzed reaction of aryl iodides with tertiary propargylic amides.: Highly substituted allenes through a regioselective carbopalladation/β-NPd elimination reaction |
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Authors: | Antonio Arcadi Giancarlo Fabrizi Luca M Parisi |
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Affiliation: | 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 |
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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. |
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Keywords: | Palladium Allenes Hydroarylation Alkynes |
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