title: Copper-mediated C6-selective dehydrogenative heteroarylation of 2-pyridones with 1,3-azoles.
abstract: A copper-mediated C6-selective dehydrogenative heteroarylation of 2-pyridones with 1,3-azoles has been developed. The reaction proceeded smoothly by twofold C-H cleavage even in the absence of noble-metal catalysts. The observed site selectivity was directed by a pyridyl substituent on the nitrogen atom of the pyridone ring. This directing group was readily removed after the coupling event, thus leading to 2-pyridone derivatives with a free N-H group. Moreover, in some cases, catalytic turnover of the Cu salt was also possible with the ideal terminal oxidant: molecular oxygen in air.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan).
authors.forename: Riko
authors.initials: R
authors.lastname: Odani
authors.forename: Koji
authors.initials: K
authors.lastname: Hirano
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Satoh
authors.forename: Masahiro
authors.initials: M
authors.lastname: Miura
mesh_terms: D001393:Azoles / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006865:Hydrogenation; D016877:Oxidants / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D011728:Pyridones / Q000737:chemistry*
chemical_list: D001393:Azoles; D016877:Oxidants; D011728:Pyridones; C017679:2-hydroxypyridine; D003300:Copper; D010100:Oxygen
keywords: CH cleavage; arylation; copper; pyridones; synthetic methods