Mechanistic Studies: Based on the above experiments and previous reports, we propose a concise catalytic cycle as depicted in Figure . The two fluorene groups at the 3,3'-positions of the naphthalene skeleton effectively shield one of the sides of the pyridine structure, respectively, thus establishing a chiral enclave. The copper catalyst M1, coordinating with bipyridine and amine, would interact with the cyclic diaryliodonium 9a, followed by oxidative addition, to form an axially chiral copper intermediate M3. The subsequent reductive elimination of M3 produced the target axially chiral product 11 and a monovalent copper species M4. The catalytic sequence comes full cycle with the reassociation of M4 with amine to form copper species M1.