M Ángeles Fuentes1, Riccardo Gava1, Noam I Saper2, Erik A Romero2, Ana Caballero1, John F Hartwig2, Pedro J Pérez1. 1. Laboratorio de Catálisis Homogénea, Unidad Asociada al CSIC, CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química, Universidad de Huelva, 21007, Huelva, Spain. 2. Department of Chemistry, University of California, Berkeley, CA, 94720, USA.
Abstract
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.
The functionalization of C-H bonds in light alkanes, partin class="Chemical">cularly 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.
Authors: José María Muñoz-Molina; Daniel Bafaluy; Ignacio Funes-Ardoiz; Adiran de Aguirre; Feliu Maseras; Tomás R Belderrain; Pedro J Pérez; Kilian Muñiz Journal: Organometallics Date: 2022-04-29 Impact factor: 3.837