Carbene-Catalyzed Tandem Imine Umpolung-Intramolecular Aza-Conjugate Addition-Oxidation to Access N-Substituted Isoindolinones.

Abstract

Herein, we have described a novel N-heterocyclic carbene (NHC)-catalyzed synthesis of N-substituted isoindolinone acetates. The presented transformation proceeds through NHC-catalyzed tandem imine umpolung-intramolecular aza-Michael addition followed by oxidation, while molecular oxygen in air acts as a sole oxidant. Atom efficiency, operational simplicity, large-scale syntheses, and mild reaction conditions are the salient features of this method. Mechanistic studies were indicative of the necessity of molecular oxygen in air as oxidant for the conversion of imine to amide.