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Copper‐Catalyzed Dehydrogenative Amidation of Light Alkanes

The functionalization of C−H bonds in light alkanes, particularly to form C−N bonds, remains a challenge. We report the dehydrogenative coupling of amides with C1–C4 hydrocarbons to form N‐alkyl amide products with tBuOOtBu as oxidant, and a copper complex of a phenanthroline‐type ligand as catalyst...

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Detalles Bibliográficos
Autores principales: Fuentes, M. Ángeles, Gava, Riccardo, Saper, Noam I., Romero, Erik A., Caballero, Ana, Hartwig, John F., Pérez, Pedro J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8457245/
https://www.ncbi.nlm.nih.gov/pubmed/33979475
http://dx.doi.org/10.1002/anie.202104737
Descripción
Sumario:The functionalization of C−H bonds in light alkanes, particularly to form C−N bonds, remains a challenge. We report the dehydrogenative coupling of amides with C1–C4 hydrocarbons to form N‐alkyl amide products with tBuOOtBu as oxidant, and a copper complex of a phenanthroline‐type ligand as catalyst. The reactions occurred in good yields in benzene or supercritical carbon dioxide as solvents. This strategy allowed for the determination of the relative reactivity of these alkane C−H bonds toward this amination process and showed, in contrast to prior work with larger alkanes, that the reactivity correlated with bond dissociation energies.