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

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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… Click to show full 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: coupling alkenes; iron; hydrogen atom; atom transfer

Journal Title: ACS Catalysis
Year Published: 2018

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