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

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ID: J42-Y1999-380