Ir(III)-Catalyzed Stereoselective Haloamidation of Alkynes Enabled by Ligand Participation

Abstract

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)(κ2-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. © 2018 American Chemical Society