Cu-catalyzed oxygenation of alkene-tethered amides with O2: Via unactivated CC bond cleavage: A direct approach to cyclic imides

Abstract

The transformations of unactivated alkenes through CC bond double cleavage are always attractive but very challenging. We report herein a chemoselective approach to valuable cyclic imides by a novel Cu-catalyzed geminal amino-oxygenation of unactivated CC bonds. O2 was successfully employed as the oxidant as well as the O-source and was incorporated into alkenyl amides via CC bond cleavage for the efficient preparation of succinimide or glutarimide derivatives. Moreover, the present strategy under simple conditions can be used in the late-stage modification of biologically active compounds and the synthesis of pharmaceuticals, which demonstrated the potential application.