Treatment of aromatic nitriles with methyllithium produces N-lithiated imine reagents which, when reacted with (η(2)-cyclooctene)(Cl)Ir(PMe(3))(3), generate fused iridaazacycles via ortho-metallation. Mono-protonation of these iridaazacycles produces fused iridapyrrole derivatives, while di-protonation leads to several different pathways.