Copper-Catalyzed Deaminative Amination of Primary Amines Enabled by a Deaminating Reagent.

We report a copper-catalyzed deaminative sp3 C-N cross-coupling of primary alkyl amines with N-heteroarenes, enabled by a deaminating reagent that generates alkyl radicals in situ. The method features general conditions, a broad substrate scope, excellent functional group tolerance, and successful late-stage functionalization of bioactive compounds. Mechanistic studies support a radical cross-coupling pathway. This approach significantly expands the scope of alkyl radical precursors for copper-mediated sp3 C-N bond formation.