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

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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 40°C and on rare occasions in DMF from 24 to 80°C. 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

see article for more examples

Silylations with TBDPSCl

see article for more reactions

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P(MeNCH₂CH₂)₃N:  An Efficient Catalyst for the Desilylation of tert-Butyldimethylsilyl Ethers

Z. Yu, J. G. Verkade, J. Org. Chem., 2000, 65, 2065-2068.

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Key Words

Silylation, TBDMS Ethers, TBDPS Ethers

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ID: J54-Y1997-370