Photoinduced Controllable Synthesis of α-Oximino Ketone and α-Imino Ketones from Nitrostyrene Via NO Radical Migration and Rearrangement.

A photoinduced strategy for the direct and precise construction of α-oximino ketones and α-imino ketones from nitrostyrenes was established. Upon photoexcitation, NO radical was generated from a nitro group, which undergoes intramolecular migration to the adjacent carbon atom to afford the oxime and imine unit by judicious tuning of substrate substituents, solvent, and reaction time. This photoinduced divergent transformation features mild reaction conditions, good functional group compatibility, gram-scale synthesis, good selectivity, and without the requirement of external NO sources.