Shvo's Catalyst and [IrCp*Cl2(amidine)] Effectively Catalyze the Formation of Tertiary Amines from the Reaction of Primary Alcohols and Ammonium Salts

The reaction of (pentamethylcyclopentadienyl) iridium dichloride dimer, [IrCp*Cl-2](2), with bis(2,4,6-trimethylphenyl)formamidine allows the preparation of two new [IrCp*Cl-2(amidine)] and [IrCp*Cl(amidinate)] complexes, which have been fully characterized. Both complexes have been tested in the beta-alkylation of 1-phenylethanol with primary alcohols, and in the formation of tertiary amines from the reaction of ammonium salts with primary alcohols, and the results have been compared with those shown by Shvo's catalyst. Our studies demonstrate that both [IrCp*Cl-2(amidine)] and Shvo's catalyst are very efficient in both catalytic processes. The high activity of the Ir-amidine complex may be attributed to the presence of the NH group in the amidine ligand.