Copper-Catalyzed Selective Oxidative Acylation of Secondary Anilines with Ethyl Glyoxalate: Domino Synthesis of Indoline-2,3-diones

A novel, easy and useful copper-catalyzed selective acylation of secondary anilines with ethyl glyoxalate has been developed, and the corresponding indoline-2,3-dione derivatives were prepared. The procedure comprises the sequential intermolecular copper-catalyzed selective oxidative ortho-site aromatic acylation of the NH group in secondary anilines and intramolecular nucleophilic attack of the NH group to the ester. The inexpensive, easy and efficient method should provide a new strategy for synthesis of dicarbonyl compounds.