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Protic NHC (PNHC) complexes with N1H, N2-alkyl/aryl imidazolylidene ligands are relatively rare, and routes for their synthesis differ from what is used to make non-protic analogs. Prior work from our group and others showed that in the presence of a tethering ligand (phosphine or in one case, pyridine), CpM and Cp*M (M = Ir, Ru) PNHC complexes could be made by heating. Here, we find that the use of ionizing agents to activate [Cp*MIIICl(μ-Cl)]2 (M = Ir, Rh) allows for what we believe is unprecedented ambient temperature formation of PNHC complexes from neutral imidazoles; the product complexes are able to perform transfer hydrogenation.

Cationic Protic Imidazolylidene NHC Complexes of Cp*IrCl+ and Cp*RhCl+ with a Pyridyl Tether Formed at Ambient Temperature

Cationic Protic Imidazolylidene NHC Complexes of CpIrCl+ and CpRhCl+ with a Pyridyl Tether Formed at Ambient Temperature