Photoassisted, iron-catalyzed allylic amination of olefins with nitroarenes

Olefins react with nitroarenes and carbon monoxide photochemically in the presence of [Cp*Fe(CO)2]2 (Cp*=η5-C5Me5) to produce N-aryl-N-allyl amines in moderate to good yields. Unsymmetrical olefins react highly regioselectively with N-functionalization at the less substituted vinylic carbon. Mechanistic probes using 2′-nitrobiphenyl, 2,3-dimethylbutadiene and nitrosobenzene suggest that neither aryl nitrenes nor nitrosoarenes are the active aminating agents in these reactions.