Olefin epoxidation with inorganic peroxides. Solutions to four long-standing controversies on the mechanism of oxygen transfer

Accounts of Chemical Research
Dirk V DeubelJörg Sundermeyer

Abstract

Four controversies on the mechanism of the olefin epoxidation with Mimoun-type complexes, [MoO(O2)2(OPR3)], Herrmann-type complexes, [ReO(O2)2Me], and related inorganic peroxides have inspired industrial and academic researchers in the last three decades. First, is the oxygen transfer from the peroxo complex to the olefin concerted or stepwise? Second, does the oxidant act as an electrophile or a nucleophile? Third, is the mechanism of the stoichiometric reaction also valid for catalytic protocols? Fourth, how can stereochemical information be transferred between oxidant and substrate? In this Account, we discuss answers to the long-standing questions, focusing on recent contributions from quantum chemical calculations.

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Citations

Nov 20, 2012·Accounts of Chemical Research·Zhi Li, Hisashi Yamamoto
Nov 18, 2015·Journal of Chemical Theory and Computation·Lianrui Hu, Hui Chen
Apr 6, 2017·Chemistry : a European Journal·Wenbao MaZhenshan Hou
Sep 27, 2014·Physical Chemistry Chemical Physics : PCCP·Xi LiuMarco Conte
Sep 20, 2006·Chemistry : a European Journal·Keigo KamataNoritaka Mizuno
Mar 4, 2005·Chemistry : a European Journal·Justin Kai-Chi Lau, Dirk V Deubel
Feb 26, 2008·Angewandte Chemie·M Pilar del RíoCristina Tejel
May 28, 2008·Chemistry : a European Journal·Wioletta KośnikMarek Chmielewski
Oct 1, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Maria José Calhorda, Paulo Jorge Costa
Jan 29, 2019·Chemistry : a European Journal·Qingqing ZhouZhenshan Hou
Mar 7, 2006·Dalton Transactions : an International Journal of Inorganic Chemistry·Luís F VeirosMaria José Calhorda
Apr 12, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Matthew HerbertAgustín Galindo
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Feb 18, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·M Luísa RamosHugh D Burrows
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