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

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...

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Detalles Bibliográficos
Autores: Saladrigas, Mar, Loren, Guillem, Bonjoch i Sesé, Josep, Bradshaw, Ben
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2018
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/128361
Acceso en línea:https://hdl.handle.net/2445/128361
Access Level:acceso abierto
Palabra clave:Amines
Alquens
Catàlisi
Enllaços químics
Química orgànica
Alkenes
Catalysis
Chemical bonds
Organic chemistry
Descripción
Sumario: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