Nickel-Catalyzed Synthesis of Diarylamines via Oxidatively Induced C–N Bond Formation at Room Temperature

A nickel-catalyzed oxidative coupling of zinc amides with organomagnesium compounds selectively produces diarylamines under mild reaction conditions, with tolerance for chloride, bromide, hydroxyl, ester, and ketone groups. A diamine is bis-monoarylated. A bromoaniline undergoes N-arylation followed by Kumada–Tamao–Corriu coupling in one pot. The reaction may proceed via oxidatively induced reductive elimination of a nickel species.