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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.
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Bleeke et al. (2008) studied this question.
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