Oxidative Nickel-Catalyzed ortho-C–H Amination of (Iso)quinolines with Alicyclic Amines Directed by a Sacrificial N-Oxide Group

Transition metal (TM)-catalyzed direct amination of C–H bonds on free or fused pyridine (Py) rings with free amines still remains scarce because amines and the Py ring tend to adopt a nonproductive N-bound coordination with many TMs, leading to a significant decrease of catalytic reactivity. We herein disclose a nickel-catalyzed and a sacrificial N-oxide group directed oxidative coupling of (iso)quinolyl C–H bonds and alicyclic amines, which furnishes bioimportant amino(iso)quinolines efficiently and selectively in a single step. Noteworthy, this protocol avoids the use of aggressive reactants and very strong bases usually required when aminating on nonoxidized Py rings.