A copper-catalyzed annulation of O-acyl oximes with cyclic 1,3-diones has been developed for the concise synthesis of 7,8-dihydroindolizin-5(6H)-ones and cyclohexanone-fused furans through the substituent-controlled selective radical coupling process. 2-Alkyl cyclic 1,3-diones undergo C–C radical coupling, while 2-unsubstituted cyclic 1,3-diones undergo C–O radical coupling.

A copper-catalyzed annulation of α,β-unsaturated O-acyl ketoximes with isoquinolinium N-ylides has been developed for the concise synthesis of stable N–H imines with a benzo­[7,8]­indolizine core. When β-(2-bromoaryl)-α,β-unsaturated O-acyl ketoximes are used as the starting materials, a cascade cyclization occurs to afford the benzo­[7,8]­indolizino­[1,2-c]­quinolines.