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

摘要

Iron complexes derived from a bis-isoindoline-bis-pyridine ligand platform based on the BPBP ligand (BPBP = N,N '-bis(2-picolyl)-2,2 '-bispyrrolidine) 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 degrees/2 degrees 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.