title: Copper-mediated hydroxylation of arenes and heteroarenes directed by a removable bidentate auxiliary.
abstract: A copper-mediated C-H hydroxylation of arenes and heteroarenes using our newly developed PIP directing group has been developed. This procedure is scalable and compatible with a wide range of functional groups and heteroarenes, providing an operationally simple protocol for the synthesis of o-hydroxybenzamides. The hydroxylation of nicotinamides gave 4-oxo-1,4-dihydropyridine-3-carboxamides selectively. Preliminary mechanistic studies implicate that a basic ligand-enabled, irreversible, rate-determining CMD step is most likely involved in this process.
authors.affiliation: Department of Chemistry, Zhejiang University , Hangzhou 310027, China.
authors.forename: Xin
authors.initials: X
authors.lastname: Li
authors.forename: Yan-Hua
authors.initials: YH
authors.lastname: Liu
authors.forename: Wen-Jia
authors.initials: WJ
authors.lastname: Gu
authors.forename: Bo
authors.initials: B
authors.lastname: Li
authors.forename: Fa-Jie
authors.initials: FJ
authors.lastname: Chen
authors.forename: Bing-Feng
authors.initials: BF
authors.lastname: Shi
mesh_terms: D001549:Benzamides / Q000138:chemical synthesis* / Q000737:chemistry; D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004095:Dihydropyridines; D006900:Hydroxylation; D008024:Ligands; D015394:Molecular Structure; D010636:Phenols
chemical_list: D001549:Benzamides; D001555:Benzene Derivatives; D004095:Dihydropyridines; D008024:Ligands; D010636:Phenols; D003300:Copper; C038806:1,4-dihydropyridine