Palladium-catalyzed reaction of aryl iodides with tertiary propargylic amides.: Highly substituted allenes through a regioselective carbopalladation/β-NPd elimination reaction

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.