Cu-catalyzed oxygenation of alkene-tethered amides with O₂ via unactivated C[double bond, length as m-dash]C bond cleavage: a direct approach to cyclic imides.

ABSTRACT: The transformations of unactivated alkenes through C[double bond, length as m-dash]C 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 C[double bond, length as m-dash]C bonds. O₂ was successfully employed as the oxidant as well as the O-source and was incorporated into alkenyl amides via C[double bond, length as m-dash]C 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.

SUBMITTER: Li J 

PROVIDER: S-EPMC6889834 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature