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Oxidation of Carbon-Silicon Bonds: The Dramatic Advantage of Strained Siletanes

James D. Sunderhaus, Hubert Lam, and Gregory B. Dudley*

*Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, Email: gdudleychem.fsu.edu

J. D. Sunderhaus, H. Lam, G. B. Dudley, Org. Lett., 2003, 8, 4571-4573.

DOI: 10.1021/ol035695y (free Supporting Information)


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Abstract

Various siletanes have been used as substrates for the oxidation of carbon-silicon bonds upon exposure to aqueous fluoride and peroxide. These tetraalkylsilanes offer a combination of stability and reactivity with many practical benefits, including compatibility with silicon protecting groups and electron-rich aromatic rings.

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Key Words

Alkylsilanes, Vinylsilanes, Arylsilanes, Alcohols, Phenols, Tamao-Fleming Oxidation


ID: J54-Y2003-1270