A palladium-catalyzed oxidative carbo-heterofunctionalization of aniline derivs. involving concomitant direct C-H functionalization and C-X bond formation was developed. By simply changing the reaction conditions (solvent and catalyst), either 3,3'-disubstituted oxindole or spirooxindole was accessible from the same starting material. E.g., reaction of acrylanilide I in presence of Pd(OAc)2 and PhI(OAc)2 gave 54% oxindole II. [on SciFinder (R)]