100009-32-3Relevant academic research and scientific papers
Nonionic superbase-catalyzed silylation of alcohols
D'Sa, Bosco A.,McLeod, Dale,Verkade, John G.
, p. 5057 - 5061 (1997)
Herein we report a very effective and mild procedure for the silyl protection of a wide variety of substrate alcohols, including primary, secondary, allylic, propargylic, benzylic, hindered secondary, tertiary, acid-sensitive, and base-sensitive alcohols and also hindered phenols. The silylation reagent used is tert-butyldimethylsilyl chloride (TBDMSCl) and the catalyst is P(MeNCH2CH2)3N, 1b, both of which are commercially available. The reactions are carried out in acetonitrile from 24 to 40 °C and on rare occasions in DMF from 24 to 80 °C. The effect of solvent, catalyst concentration, and temperature and reaction time on the silylation of alcohols and the excellent compatibility of our method with a variety of functional groups is discussed. An efficient method for recycling the catalyst is also presented. Although representative primary alcohols, secondary alcohols, and phenols were silylated using the more sterically hindered reagent tert-butyldiphenylsilyl chloride (TBDPSCl) in the presence of lb as a catalyst, tertiary alcohols were recovered unchanged.
Solvent-modulated Pd/C-catalyzed deprotection of silyl ethers and chemoselective hydrogenation
Ikawa, Takashi,Hattori, Kazuyuki,Sajiki, Hironao,Hirota, Kosaku
, p. 6901 - 6911 (2007/10/03)
Recently we have reported undesirable and frequent deprotection of the TBDMS protective group of a variety of hydroxyl functions occurred under neutral and mild hydrogenation conditions using 10% Pd/C in MeOH. The deprotection of silyl ethers is susceptible to significant solvent effect. TBDMS and TES protecting groups were selectively cleaved in the presence of acid-sensitive functional groups such as TIPS ether, TBDPS ether and dimethyl acetal under hydrogenation condition using 10% Pd/C in MeOH. In contrast, chemoselective hydrogenation of reducible functional groups such as acetylene, olefin and benzyl ether, proceeds in the presence of TBDMS or TES ethers in AcOEt or MeCN.
A mild method for rapid tert-Butyldiphenylsilylation of primary and secondary alcohols
Hardinger, Steven A.,Wijaya, Ngadi
, p. 3821 - 3824 (2007/10/02)
A rapid and efficient method for the protection of primary and secondary alcohols as their tert-butyldiphenylsilyl (tBDPS) ethers was developed. Reaction of the alcohol and tBDPSCl in DMF with AgNO3, NH4NO3, or NH4ClO4 provides good yields of the corresponding silyl ethers.
