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Synthesis and Applications - The Anderson Research Group

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Carbon-Oxygen Bond Formations<br />

Tamao-Fleming Oxidations<br />

Activated silanes undergo direct oxidation to aldehydes <strong>and</strong> ketones when treated with a<br />

F - source, H 2 O 2 <strong>and</strong> base. <strong>The</strong> reaction is thought to proceed through hexa- <strong>and</strong> pentafluorosilicate<br />

intermediates.<br />

Activating groups: Benzyldimethylsilanes (BDMS) – a ‘safety-catch silanol’<br />

Dimethylsilyl ethers<br />

Allyldimethylsilanes (ADMS) – via fluorodimethylsilane<br />

Vinyl BDMS: Trost, B.M.; Ball, Z.T.; Joge, T. Angew. Chem. Int. Ed. 2003, 42, 3415-3418.<br />

Vinyl ADMS: Magar, S.S.; Fuchs, P.L. Tetrahedron Lett. 1991, 32, 7513-7516.

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