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)
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
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.
Silylation, TBDMS Ethers, TBDPS Ethers