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.

DOI: 10.1021/jo010369m

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Abstract

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

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Efficient Epoxidation of Alkenes with Aqueous Hydrogen Peroxide Catalyzed by Methyltrioxorhenium and 3-Cyanopyridine

H. Adolfsson, C. Copéret, J. P. Chiang, A. K. Yudin, J. Org. Chem., 2000, 65, 8651-8658.

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Key Words

epoxides, bis(trimethylsilyl) peroxide

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ID: J42-Y2001