title: Mechanistic study of a Pd/C-catalyzed reduction of aryl sulfonates using the Mg-MeOH-NH(4)OAc system.
abstract: A method for the deoxygenation of phenolic hydroxy groups via aryl triflates or mesylates has been established by using a combination of Pd/C-Mg-MeOH. The addition of NH(4)OAc to the system markedly accelerated the reaction rate and expanded the scope of the reaction. Mechanistic studies suggested that a single-electron transfer process from the Pd(0) center to the benzene ring is involved in the reduction of aryl sulfonates and that NH(4)OAc works as a solubilization reagent of the Mg salt and as an accelerator of the electron transfer, thus enhancing the reaction process. Our method was also applicable to the regioselective deuteration of benzene derivatives with CH(3)OD as the solvent and deuterium source: the original hydroxy group could be efficiently replaced with a deuterium atom.
authors.affiliation: Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, Mitahora-higashi 5-6-1, Gifu 502 8585, Japan.
authors.forename: Akinori
authors.initials: A
authors.lastname: Mori
authors.forename: Tomoteru
authors.initials: T
authors.lastname: Mizusaki
authors.forename: Takashi
authors.initials: T
authors.lastname: Ikawa
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Maegawa
authors.forename: Yasunari
authors.initials: Y
authors.lastname: Monguchi
authors.forename: Hironao
authors.initials: H
authors.lastname: Sajiki
mesh_terms: D000085:Acetates / Q000737:chemistry*; D001190:Arylsulfonates / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D004579:Electron Transport; D008274:Magnesium / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry*; D008956:Models, Chemical; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
chemical_list: D000085:Acetates; D001190:Arylsulfonates; D012997:Solvents; D010165:Palladium; D002244:Carbon; D008274:Magnesium; C018824:ammonium acetate; D000432:Methanol