Hypervalent Iodine(III)-Mediated 1,2-Aryl Migration in 3-Arylideneindolin-2-ones: A Route to 3-Aryloxindole Derivatives

Abstract

A new and effective metal-free method for synthesizing 3-aryloxindole derivatives through hypervalent iodine(III)-mediated 1,2-aryl migration in 3-arylideneindolin-2-ones is presented in this study. The reaction utilizes (diacetoxyiodo)benzene (DIB) in methanol to trigger skeletal oxidative rearrangement, resulting in the formation of all-carbon quaternary centers at the C3 position of oxindoles. This approach provides a mild and environmentally friendly alternative to traditional metal-catalyzed processes, offering broad substrate tolerance. Furthermore, this method provides a valuable synthetic route for constructing biologically significant 3-aryloxindole derivatives with potential pharmaceutical applications.