Copper-catalyzed intermolecular chloroazidation of α,β-unsaturated amides

A highly practical copper-catalyzed intermolecular chloroazidation of alpha,beta-unsaturated amides has been described, giving a series of azidochlorides in good-to-excellent yields. The stable azidoiodine (III) reagent and SOCl2 were used as azide and chlorine sources, respectively. The synthetic applications of this protocol were also explored by a variety of synthetically useful transformations.