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Copper‐Catalyzed Dehydrogenative Amidation of Light Alkanes
Author(s) -
Fuentes M. Ángeles,
Gava Riccardo,
Saper Noam I.,
Romero Erik A.,
Caballero Ana,
Hartwig John F.,
Pérez Pedro J.
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202104737
Subject(s) - chemistry , amination , catalysis , reactivity (psychology) , alkane , alkyl , benzene , organic chemistry , amide , photochemistry , dissociation (chemistry) , copper , supercritical fluid , medicinal chemistry , medicine , alternative medicine , pathology
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.