Dearomatization-Scission-Aromatization of Anilines: En route to Synthesis of 3,3-Disubstituted Oxindoles with Wide Heteroatom Nucleophiles

Abstract

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