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A mild, ferrocene-catalyzed C-H imidation of (hetero)arenes.

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.

SUBMITTER: Foo K

PROVIDER: S-EPMC4210156 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature

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A mild, ferrocene-catalyzed C-H imidation of (hetero)arenes.

Foo Klement K Sella Eran E Thomé Isabelle I Eastgate Martin D MD Baran Phil S PS

Journal of the American Chemical Society 20140331 14

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) play ...[more]

PMID: 24654983

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