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.
Solé
Daniel
D
Laboratori de Química Orgánica, Facultat de Farmàcia, and Institut de Biomedicina, Universitat de Barcelona, 08028 Barcelona, Spain. dsole@ub.edu
Serrano
Olga
O
D000577:Amides / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D007462:Iodobenzenes / Q000737:chemistry; D008956:Models, Chemical; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D000814:Aniline Compounds; D002264:Carboxylic Acids; D007462:Iodobenzenes; D010165:Palladium; D002244:Carbon