Olefin Epoxidation with Bis(trimethylsilyl) Peroxide Catalyzed by Inorganic Oxorhenium Derivatives. Controlled Release of Hydrogen Peroxide
Andrei K. Yudin*, Jay P. Chiang, Hans Adolfsson and Christophe Copéret
*Department of Chemistry and the Skaggs Institute of Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 90237, Email: ayudinchem.utoronto.ca
A. K. Yudin, J. P. Chiang, H. Adolfsson, C. Copéret, J. Org. Chem., 2001, 66, 4713-4718.
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Organometallic rhenium species (e.g., CH3ReO3) can be replaced by less expensive inorganic rhenium oxides (e.g., Re2O7, ReO3(OH), and ReO3) using bis(trimethylsilyl) peroxide (BTSP) as oxidant in place of aqueous H2O2. Using a catalytic amount of a proton source, controlled release of hydrogen peroxide helps preserve sensitive peroxorhenium species and enables catalytic turnover to take place.
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proposed mechanism of peroxo group transfer and catalytic cycle
H. Adolfsson, C. Copéret, J. P. Chiang, A. K. Yudin, J. Org. Chem., 2000, 65, 8651-8658.