Iron-Catalyzed C−C Bond Formation at α-Position of Aliphatic Amines via C−H Bond Activation through 1,5-Hydrogen Transfer

摘要

C−C bond formation reactions that take place through organoiron species sometimes exhibit radical-like character. The reaction of N-(2-iodophenylmethyl)dialkylamine with a Grignard or diorganozinc reagent in the presence of a catalytic amount of Fe(acac)3 gives the product resulting from arylation, alkenylation, or alkylation of the sp3 C−H bond next to the amine group in good to excellent yield. Mechanistic studies including labeling experiments indicate that the reaction involves radical translocation triggered by the formation of a radical-like species by removal of the iodide group.