The Journal of organic chemistry

Intramolecular Pd (0)-Catalyzed Reactions of β-(2-Iodoanilino) Carboxamides: Enolate Arylation and Nucleophilic Substitution at the Carboxamide Group

D Sole, O Serrano

Index: Sole, Daniel; Serrano, Olga Journal of Organic Chemistry, 2008 , vol. 73, # 23 p. 9372 - 9378

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Citation Number: 40

Abstract

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