Ir(III)-Catalyzed Reductive Amination of Carbonyl Compounds with High Selectivity

Amines are a nitrogenous class of organic compounds and functional groups found present in pharmaceuticals, agrochemicals, and many biologically relevant molecules. Traditional synthetic routes to produce amines pose various toxicity issues, poor chemoselectivity, and unstable precursor molecules. In this work, we display the reductive amination of carbonyl compounds at 37 ˚C in methanol catalyzed by a Cp*Ir(III) complex ligated by N-phenyl-2-pyridinecarboxamidate using ammonium formate as a nitrogen and hydride source. Various aromatic ketone and aldehyde substrates were run for 15 h with a catalytic loading of 1 mol % to give excellent chemoselectivity of primary amines. We plan to expand our substrate scope to α-ketoacids to demonstrate the synthetic preparation of α-amino acids.