biostudies-literatureLi JNational Basic Research Program of ChinaNational Natural Science Foundation of China9099-9103https://www.ebi.ac.uk/biostudies/studies/S-EPMC6889834biostudies-literatureUnknown10(39)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 <i>via</i> 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.Chemical scienceCu-catalyzed oxygenation of alkene-tethered amides with O₂ <i>via</i> unactivated C[double bond, length as m-dash]C bond cleavage: a direct approach to cyclic imides.PMC68898342015CB856600217720022163200181821004Jiao NLi JWang TWei JZhu BfalseCu-catalyzed oxygenation of alkene-tethered amides with O₂ <i>via</i> unactivated C[double bond, length as m-dash]C bond cleavage: a direct approach to cyclic imides.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 <i>via</i> 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.2019-01-01T00:00:00Z2019 Oct2025-04-04T20:45:22.775Z2025-04-04T20:45:22.775ZS-EPMC68898343182775210.1039/c9sc03175h