Hydrogen Atom Transfer (HAT)-Triggered Iron-Catalyzed Intra- and Intermolecular Coupling of Alkenes with Hydrazones: Access to Complex Amines

Abstract

A methodology for the coupling of alkenes with aldehyde- or ketone-derived Cbz-hydrazones to form a new C−C bond through a radical process is described. The sequence comprises an initial in situ generation of a putative iron hydride followed by a hydrogen atom transfer to an alkene, a coupling with a hydrazone, and a final reduction of the nitrogen-centered radical. Hydrogenation of the obtained hydrazines renders amines, including valuable tert-alkyl amines. KEYWORDS: HAT, iron catalysis, α-tert-amines, C−C bond formation, radical processes, synthetic methods