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B(C6F5)3-Catalyzed Silation of Alcohols: A Mild, General Method for Synthesis of Silyl Ethers

James M. Blackwell, Katherine L. Foster, Victoria H. Beck and Warren E. Piers*

*Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, Alberta T2N 1N4, Canada, Email: wpiersucalgary.ca

J. M. Blackwell, K. L. Foster, V. H. Beck, W. E. Piers, J. Org. Chem., 1999, 64, 4887-4892.

DOI: 10.1021/jo9903003 (free Supporting Information)


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Abstract

Tris(pentafluorophenyl)borane, B(C6F5)3, is an effective catalyst for a mild and efficient dehydrogenative silation of alcohols using a variety of silanes. Only the most bulky silanes (Bn3SiH and iPr3SiH) were not reactive under these conditions. Generally, the reactions are clean and high yielding, with dihydrogen as the only byproduct.

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Key Words

Silylation, TBDMS Ethers, TBDPS Ethers


ID: J54-Y1999-380