Novel imidazo[1,5-b]pyridazine-substituted (pyridyl-methyl)amines were synthesized via the nucleophilic ring transformation of oxadiazolium halides and (aminomethyl)pyridines, followed by a cyclocondensation reaction with 1,3-diketones. After deprotonation, these monoanionic amido-pincer ligands are suitable for the stabilization of mononuclear iridium complexes. For 2-(pyridyl-methyl)-amine-derived complexes, we observed the formation of dimers via an intermolecular C–C coupling reaction, whilst the 3-(pyridyl-methyl)amine-derived complex did not react. We propose that enaminetautomerization plays an important role in the C–C coupling reaction.
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