Intramolecular Pd(0)-Catalyzed Reactions of β-(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 /3-(2-iodoanilino) carboxamides. The intramolecular acylation of β-(2-iodoanilino) carboxamides reported here is the first example of a nucleophilic attack of a o-arylpalladium species at the carboxamide group, a framework that is usually inert toward organopalladium reagents.