Reactions of aromatic N-heterocycles with a lutetium benzyl complex supported by a ferrocene-diamide ligand

A comparison between the reactivity behavior of two lutetium benzyl complexes supported by different ferrocene-diamide ligands towards aromatic N-heterocycles, such as 1-methylimidazole, isoquinoline, and pyridines, is presented. The two ferrocene-diamide ancillary ligands differ in their nitrogen-donor substituent: adamantyl for one and t-butyldimethylsilyl for the other. The synthesis and characterization of the adamantyl-derived complex 1(Ad)-DME are reported. The ring opening of 1-methylimidazole by the THF analogue of 1(Ad)-DME, 1(Ad)-THF, was observed, analogously to the ring opening of the same substrate by the lutetium benzyl complex supported by the silyl-substituted ligand. Also, analogous products were observed in the reactions with isoquinoline.