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