Iron‐Catalyzed Intramolecular Arene C(sp(2))−H Amidations under Mechanochemical Conditions

In a ball mill, FeBr(3)‐catalyzed intramolecular amidations lead to 3,4‐dihydro‐2(1H)‐quinolinones in good to almost quantitative yields. The reactions do not require a solvent and are easy to perform. No additional ligand is needed for the iron catalyst. Both 4‐substituted aryl and β‐substituted di...

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Detalles Bibliográficos
Autores principales: Shi, Peng, Tu, Yongliang, Kong, Deshen, Wu, Peng, Ma, Ding, Bolm, Carsten
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9401578/
https://www.ncbi.nlm.nih.gov/pubmed/35511087
http://dx.doi.org/10.1002/anie.202204874
Descripción
Sumario:In a ball mill, FeBr(3)‐catalyzed intramolecular amidations lead to 3,4‐dihydro‐2(1H)‐quinolinones in good to almost quantitative yields. The reactions do not require a solvent and are easy to perform. No additional ligand is needed for the iron catalyst. Both 4‐substituted aryl and β‐substituted dioxazolones provide products with high selectivity. Mechanistically, an electrophilic spirocyclization followed by C−C migration explains the formation of rearranged products.

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