539814-10-3Relevant articles and documents
Pd/C-catalyzed deoxygenation of phenol derivatives using mg metal and MeOH in the presence of NH4OAc
Sajiki, Hironao,Mori, Akinori,Mizusaki, Tomoteru,Ikawa, Takashi,Maegawa, Tomohiro,Hirota, Kosaku
, p. 987 - 990 (2006)
A Pd/C-catalyzed deoxygenation method of phenolic hydroxyl groups via aryl triflates or mesylates using Mg metal in MeOH at room temperature was developed. The addition of NH4OAc dramatically affects the reactivity and reaction rate. This method is particularly attractive to provide an environmentally benign and widely applicable removal method of phenolic alcohols under quite mild reaction conditions.
Mechanistic study of a Pd/C-catalyzed reduction of aryl sulfonates using the Mg-MeOH-NH4OAc system
Mori, Akinori,Mizusaki, Tomoteru,Ikawa, Takashi,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao
, p. 1432 - 1441 (2008/02/04)
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 NH4OAc 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 Pd0 center to the benzene ring is involved in the reduction of aryl sulfonates and that NH4OAc works as a solubilization re agent 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 CH3OD as the solvent and deuterium source: the original hydroxy group could be efficiently replaced with a deuterium atom.
