Copper-Catalyzed 8-Amido Chelation-Induced Remote C-H Amination of Quinolines

A copper-catalyzed 8-amide chelation-induced remote C-H amination of quinolines has been developed. This direct amination with readily available azodicarboxylates proceeded with perfect C5-regioselectivity offering amino-substituted 8-aminoquinolines, important bioactive molecular scaffolds, in very high yields (up to 96 %). A single-electron transfer (SET)-mediated mechanism with k(H)/k(D)=1.1 was proposed after trapping of the radical intermediate.