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A Mild, Ferrocene-Catalyzed C–H Imidation of (Hetero)Arenes

[Image: see text] A simple method for direct C–H imidation is reported using a new perester-based self-immolating reagent and a base-metal catalyst. The succinimide products obtained can be easily deprotected in situ (if desired) to reveal the corresponding anilines directly. The scope of the reacti...

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Detalles Bibliográficos
Autores principales: Foo, Klement, Sella, Eran, Thomé, Isabelle, Eastgate, Martin D., Baran, Phil S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4210156/
https://www.ncbi.nlm.nih.gov/pubmed/24654983
http://dx.doi.org/10.1021/ja501879c
Descripción
Sumario:[Image: see text] A simple method for direct C–H imidation is reported using a new perester-based self-immolating reagent and a base-metal catalyst. The succinimide products obtained can be easily deprotected in situ (if desired) to reveal the corresponding anilines directly. The scope of the reaction is broad, the conditions are extremely mild, and the reaction is tolerant of oxidizable and acid-labile functionality, multiple heteroatoms, and aryl iodides. Mechanistic studies indicate that ferrocene (Cp(2)Fe) plays the role of an electron shuttle in the decomposition of the perester reagent, delivering a succinimidyl radical ready to add to an aromatic system.