A Mild, Ferrocene-Catalyzed C–H Imidation of (Hetero)Arenes
| Autor: | Eran Sella, Martin D. Eastgate, Isabelle Thome, Phil S. Baran, Klement Foo |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
Molecular Structure
Metallocenes Chemistry Communication Aryl Heteroatom General Chemistry Imides Biochemistry Decomposition Combinatorial chemistry Catalysis chemistry.chemical_compound Colloid and Surface Chemistry Ferrocene Succinimide Heterocyclic Compounds Reagent Benzene Derivatives Organic chemistry Molecule Ferrous Compounds |
| Zdroj: | Journal of the American Chemical Society |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/ja501879c |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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