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Use of Catalytic Fluoride under Neutral Conditions for Cleaving Silicon-Oxygen Bonds

Anthony M. DiLauro, Wanji Seo and Scott T. Phillips*

*Department of Chemistry, The Pennsylvania University, University Park, Pennsylvania 16802, United States, Email: sphillipspsu.edu

A. M. DiLauro, W. Seo, S. T. Phillips, J. Org. Chem., 2011, 76, 7352-7358.

DOI: 10.1021/jo200848j (free Supporting Information)


Abstract

Catalytic quantities of fluoride at neutral pH in mixed organic-aqueous solutions that contain buffer cleaved various silicon-oxygen bonds. These conditions show tolerance for acid- and base-sensitive groups. A modified procedure using catalytic fluoride in anhydrous dimethyl sulfoxide-methanol generates primarily volatile silicon byproducts.

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Key Words

Cleavage of Silyl Ethers, tert-Butyldimethylsilyl ethers


ID: J42-Y2011-2690