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Nonionic Superbase-Catalyzed Silylation of Alcohols

Bosco A. D'Sa, Dale McLeod and John G. Verkade*

*Department of Chemistry, Gilman Hall, Iowa State University, Ames, Iowa 50011, Email: jverkadeiastate.edu

B. A. D'Sa, D. McLeod, J. G. Verkade, J. Org. Chem., 1997, 62, 5057-5061.

DOI: 10.1021/jo9701492 (free Supporting Information), DOI: 10.1021/jo9840123 (Corrections)


Abstract

A commercially available proazaphosphatrane is an efficient and mild catalyst for the silylation of a wide variety of alcohols and phenols, including acid-sensitive, base-sensitive, and hindered substrates, using tert-butyldimethylsilyl chloride (TBDMSCl). The reactions are carried out in acetonitrile from 24 to 40C and on rare occasions in DMF from 24 to 80C. Although representative primary alcohols, secondary alcohols, and phenols were silylated using the more sterically hindered reagent tert-butyldiphenylsilyl chloride (TBDPSCl), tertiary alcohols were recovered unchanged.

Silylations with TBDMSCl

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Silylations with TBDPSCl

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Key Words

Silylation, TBDMS Ethers, TBDPS Ethers


ID: J54-Y1997-370