Described herein is the application of a strategy of ligand participation for the Ir-catalyzed imido transfer into alkynes. On the basis of a stoichiometric [3 + 2] cycloaddition of Cp*Ir(III)(kappa(2)-N,O-chelate) with alkynyl dioxazolone, a catalytic haloamidation was developed for the first time by employing [Cp*IrCl2](2) precatalyst and NaX salts (X = Cl or Br) as practical halide sources to furnish synthetically versatile Z-(halovinyl)lactams with excellent stereoselectivity.