Intramolecular Pd(0)-catalyzed reactions of beta-(2-iodoanilino) carboxamides: enolate arylation and nucleophilic substitution at the carboxamide group.

Two different reaction pathways, the enolate arylation and the acylation of the aryl halide, can be promoted by a Pd(0) catalyst starting from beta-(2-iodoanilino) carboxamides. The intramolecular acylation of beta-(2-iodoanilino) carboxamides reported here is the first example of a nucleophilic attack of a sigma-arylpalladium species at the carboxamide group, a framework that is usually inert toward organopalladium reagents.