Copper‐Catalyzed Cyclization and Azidation of γ,δ‐Unsaturated Ketone O‐Benzoyl Oximes

Abstract

Abstract An intramolecular imination/azidation sequence has been realized through the tetrakis(acetonitrile)copper(I) hexafluorophophate [Cu(CH 3 CN) 4 PF 6 ]‐catalyzed reaction of γ,δ‐unsaturated ketone O ‐benzoyl oximes with trimethylsilyl azide (TMSN 3 ). The reaction proceeds via the copper‐mediated NO cleavage and subsequent CN forming 5‐ exo cyclization. The thus formed intermediate is then azidated to afford the corresponding dihydropyrrole product. Preliminary mechanistic investigations suggest that the cyclization step does not involve a radical intermediate. magnified image