Copper-Catalyzed C–H Oxidative Radical Functionalization and Annulation of Aniline-Linked 1,7-Enynes: Evidence for a 1,5-Hydride Shift Mechanism

A new copper-catalyzed tandem C–H oxidative radical functionalization and annulation of aniline-linked 1,7-enynes with alkyl nitriles or acetone is described. This reaction allows the selective construction of 1H-cyclopenta­[c]­quinolines and benzo­[j]­phenanthridin-6­(5H)-ones which rely on the substitution effect at the 2-position of the acrylamide moiety. The mechanism involving a 1,5-hydride shift process is proposed according to the control deuterium-labeled experiment.