Non-Heme Iron Catalysts with a Rigid Bis-Isoindoline Backbone and Their Use in Selective Aliphatic C−H Oxidation

Abstract

Iron complexes derived from a bis-isoindoline-bis-pyridine ligand platform based on the BPBP ligand (BPBP=N,N′-bis(2-picolyl)-2,2′-bis-pyrrolidine) have been synthesized and applied in selective aliphatic C−H oxidation with hydrogen peroxide under mild conditions. The introduction of benzene moieties on the bis-pyrrolidine backbone leads to an increased preference of tertiary over secondary C−H bond oxidation (3°/2° ratio up to 33). On the other hand, substituting the meta-position of the pyridines with bulky silyl groups affords enhanced secondary C−H oxidation selectivity and generally leads to higher product yields and mass balances.