Epoxidation of alkenes with hydrogen peroxide catalyzed by selenium-containing dinuclear peroxotungstate and kinetic, spectroscopic, and theoretical investigation of the mechanism

Inorganic Chemistry
Keigo KamataNoritaka Mizuno

Abstract

The dinuclear peroxotungstate with a SeO(4)(2-) ligand, (TBA)(2)[SeO(4){WO(O(2))(2)}(2)] (I; TBA = [(n-C(4)H(9))(4)N](+)), could act as an efficient homogeneous catalyst for the selective oxidation of various kinds of organic substances such as olefins, alcohols, and amines with H(2)O(2) as the sole oxidant. The turnover frequency (TOF) was as high as 210 h(-1) for the epoxidation of cyclohexene catalyzed by I with H(2)O(2). The catalyst was easily recovered and reused with maintenance of the catalytic performance. The SeO(4)(2-) ligand in I played an important role in controlling the Lewis acidity of the peroxotungstates, which significantly affects their electrophilic oxygen-transfer reactivity. Several kinetic and spectroscopic results showed that the present catalytic epoxidation included the following two steps: (i) formation of the subsequent peroxo species [SeW(m)O(n)](o-) (II; m = 1 and 2) by the reaction of I with an olefin and (ii) regeneration of I by the reaction of II with H(2)O(2). Compound I was the dominant species under steady-state turnover conditions. The reaction rate for the catalytic epoxidation showed a first-order dependence on the concentrations of olefin and I and a zero-order dependence on the concent...Continue Reading

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Citations

Jul 30, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Mauro CarraroMarcella Bonchio
Sep 7, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Qiaofei XuJingyang Niu
May 11, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Keigo KamataNoritaka Mizuno
Aug 10, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Xinyi MaJingping Wang
Aug 14, 2012·Chemical Society Reviews·Xavier LópezJosep M Poblet
Nov 13, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Jean-Yves PiquemalJean-Marie Brégeault
Oct 26, 2011·Angewandte Chemie·Keigo KamataNoritaka Mizuno
Jul 22, 2021·Chemistry, an Asian Journal·Wenchao ChenXinyi Ye
Oct 6, 2012·The Journal of Organic Chemistry·Shigekazu Yamazaki
May 13, 2015·Chemical Reviews·Sa-Sa Wang, Guo-Yu Yang

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