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Nickel-catalyzed reductive and borylative cleavage of aromatic carbon-nitrogen bonds in N-aryl amides and carbamates.

The nickel-catalyzed reaction of N-aryl amides with hydroborane or diboron reagents resulted in the formation of the corresponding reduction or borylation products, respectively. Mechanistic studies revealed that these reactions proceeded via the activation of the C(aryl)-N bonds of simple, electronically neutral substrates and did not require the presence of an ortho directing group.