In 1951, reported seminal studies on radical 1,2-halogen shift without the aid of π-systems, which mechanistically involves either the halogen-radical-bridged cyclic transition state or halogen-radical elimination and readdition. Recently, π-system-independent radical 1,n-heteroatom FGs (mainly B-, Si-, 10 P-atom ) migration reactions via sequential cyclization on the lone electron pair or empty p-orbital of the heteroatom and β-scission were successively disclosed by Studer, 9a,b Han 11 and others. Inspired by the aforementioned successes, we wanted to examine whether the radical 1,2-N-shift without the aid or involvement of a π-system can occur using our recently developed radical cascade strategy ─ merging radical 1,n-migration with cross-coupling reaction. 12 However, to the best of our knowledge, π-system-independent radical 1,2-N-migration, especially radical cascade merging such a 1,2-N-shift with C-H bond coupling via a C(sp 3 )-centered radical, is still unknown. In general, the as-formed C(sp 3 )-centered radical in these previously reported 1,n-functionalities migrations (including C, N, B, P-centered groups) are terminated by common processes, such as hydrogen atom transfer (HAT), single-electron transfer (SET) oxidation.