92976-55-1Relevant articles and documents
One-step conversion of formate esters to O-silyl ethers by means of samarium diiodide in the presence of chlorosilane reagents
Honda, Toshio,Ishikawa, Fumihiro
, p. 3323 - 3328 (1999)
One-step conversion of various types of formate esters into the corresponding O-silyl ethers under neutral reaction conditions was established by employing samarium diiodide in the presence of chlorosilane reagents.
Synthesis and properties of fluorous benzoquinones and their application in deprotection of silyl ethers
Matsubara, Hiroshi,Maegawa, Takahiko,Kita, Yasuaki,Yokoji, Takato,Nomoto, Akihiro
supporting information, p. 5442 - 5447 (2014/07/21)
1,4-Benzoquinone derivatives bearing trifluoromethyl, perfluorobutyl and perfluorohexyl groups were prepared and employed in the deprotection of silyl ethers. The fluorous character of these compounds was examined by measuring the partition coefficient between the fluorous and organic solvents. The benzoquinone derivatives showed significant fluorous character, indicating that they can be recovered from the reaction mixtures using a fluorous/organic biphasic system. The oxidising ability of the fluorous benzoquinones was estimated by cyclic voltammetry, and these compounds were found to be strong oxidisers. The fluorous benzoquinones were utilised in the oxidative desilylation of silyl ethers to afford the deprotected alcohols in high yield. In addition, the reduced fluorous benzoquinones were recovered from the reaction mixtures in good yields using a fluorous/organic biphasic system. This journal is the Partner Organisations 2014.
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.
Nonionic superbase-catalyzed silylation of alcohols
D'Sa, Bosco A.,McLeod, Dale,Verkade, John G.
, p. 5057 - 5061 (2007/10/03)
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.
A novel method for direct conversion of tetrahydropyranyl ethers into t-butyldimethylsilyl ethers with t-butyldimethylsilyl triflate and dimethyl sulfide
Kim,Kee
, p. 2899 - 2900 (2007/10/02)
Direct conversion of THP ethers into TBS ethers has been achieved with TBSOTf and dimethyl sulfide in dichloromethane.
1,1,3,3-TETRAMETHYLGUANIDINE: AN EFFECTIVE CATALYST FOR THE t-BUTYLDIMETHYLSILYLATION OF ALCOHOLS
Kim, Sunggak,Chang, Heung
, p. 899 - 904 (2007/10/02)
Reaction of alcohols with equimolar amounts of t-butyldimethylchlorosilane and triethylamine in the presence of 1,1,3,3-tetramethylguanidine as a catalyst affords the t-butyldimethylsilyl ethers in high yields.
