A Mild, Ferrocene-Catalyzed C–H Imidation of (Hetero)Arenes
Journal of the American Chemical Society2014Vol. 136(14), pp. 5279–5282
Citations Over TimeTop 1% of 2014 papers
Abstract
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 (Cp2Fe) 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.
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