Dearomatization–scission–aromatization of anilines: En route to synthesis of 3,3-disubstituted oxindoles with a wide range of heteroatom nucleophiles

Herein, we report a catalytic, redox-neutral method for the difunctionalization of oxindoles using ketimines derived from anilines and heteronucleophiles. The reaction proceeds through a dearomatization-aromatization strategy <i>via</i> a tetra-substituted alkene intermediate stabilized by extended resonance, facilitating the selective formation of 3,3-disubstituted oxindoles with a wide chemical space in good-to-high yields.