Highly selective, recyclable epoxidation of allylic alcohols with hydrogen peroxide in water catalyzed by dinuclear peroxotungstate

Chemistry : a European Journal
Keigo KamataNoritaka Mizuno

Abstract

The highly chemo-, regio-, and diastereoselective and stereospecific epoxidation of various allylic alcohols with only one equivalent of hydrogen peroxide in water can be efficiently catalyzed by the dinuclear peroxotungstate, K2[[W(=O)(O2)2(H2O)]2(mu-O)].2H2O (I). The catalyst is easily recycled while maintaining its catalytic performance. The catalytic reaction mechanism including the exchange of the water ligand to form the tungsten-alcoholate species followed by the insertion of oxygen to the carbon-carbon double bond, and the regeneration of the dinuclear peroxotungstate with hydrogen peroxide is proposed. The reaction rate shows first-order dependence on the concentrations of allylic alcohol and dinuclear peroxotungstate and zero-order dependence on the concentration of hydrogen peroxide. These results, the kinetic data, the comparison of the catalytic rates with those for the stoichiometric reactions, and kinetic isotope effects indicate that the oxygen transfer from a dinuclear peroxotungstate to the double bond is the rate-limiting step for terminal allylic alcohols such as 2-propen-1-ol (1a).

Citations

Apr 6, 2017·Chemistry : a European Journal·Wenbao MaZhenshan Hou
Sep 8, 2016·Chemistry : a European Journal·Cedric L Hugelshofer, Thomas Magauer
Sep 20, 2006·Chemistry : a European Journal·Keigo KamataNoritaka Mizuno
Oct 28, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Andrew J StapletonRobert C Burns
Feb 14, 2006·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Noritaka Mizuno, Kazuya Yamaguchi
Sep 27, 2018·Pharmaceutical Research·Hasitha RathnayakaChristian Schöneich
Sep 16, 2011·Chemical Communications : Chem Comm·Akimitsu OkamotoShuji Ikeda
Jun 30, 2021·Langmuir : the ACS Journal of Surfaces and Colloids·Qingqing ZhouZhenshan Hou
Jul 22, 2021·Chemistry, an Asian Journal·Wenchao ChenXinyi Ye
Jan 16, 2014·Journal of the American Chemical Society·Chuan Wang, Hisashi Yamamoto
May 13, 2015·Chemical Reviews·Sa-Sa Wang, Guo-Yu Yang
Jan 13, 2005·Journal of the American Chemical Society·Kazuya YamaguchiNoritaka Mizuno

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