126644-72-2Relevant academic research and scientific papers
NFSI/KF mediated mild and chemoselective interconversion of aryl TBDMS ethers to their benzene sulfonate
Dond, Bharat D.,Thore, Shivaji N.
supporting information, (2020/02/06)
A one pot protocol for the transformation of aryl TBDMS ethers to corresponding benzene sulfonate esters using NFSI (N-flurobenzenesulfonimide)/KF is described. In situ generation of benzenesulfonyl fluoride directs chemoselective cleavage of aryl silyl ethers over alkyl silyl ethers. Electron withdrawing substituent's on aryl ring provided better yield than donating groups. Protecting groups and sensitive functionalities are well tolerated in this methodology. Thus, commercially available inexpensive reagents, mild reaction conditions and step economy are the advantages of this method.
Preparation of nano silica supported sodium hydrogen sulfate: As an efficient catalyst for the trimethyl, triethyl and t-butyldimethyl silylations of aliphatic and aromatic alcohols in solution and under solvent-free conditions
Abri, Abdolreza,Ranjdar, Somayeh
, p. 929 - 934 (2014/10/16)
Nano silica supported sodium hydrogen sulfate has been prepared by mixing NaHSO4 with activated Nano silicagel. We wish to report a new method for the synthesis of trimethyl (TMS), triethyl (TES) and t-butyldimethyl silyl (TBS) ethers from benzylic, allylic, propargylic alcohols, phenols, naphtholes and some of phenolic drugs in the solution and under solvent-free conditions.
A mild and highly efficient method for the preparation of silyl ethers using Fe(HSO4)3/Et3N by chlorosilanes
Abri, Abdolreza,Assadi, Mohammad Galeh,Pourreza, Samira
, p. 1449 - 1454 (2013/03/13)
Avery efficient and mild procedure for preparation of silyl ethers from benzylic, allylic, propargilic alcohols, phenols, naphtoles and some of phenolic drugs with trimethylsilylchloride (TMSCl), triethylsilylchloride (TESCl) and t-buthyldimethylsilyl chloride (TDSCl) ethers in the presence of Fe(HSO 4)3/Et3N in roomtemperature in excellent yields is reported. This procedure also allows the excellent selectivity for silylation of alcohols and phenols.
The effect of solvent accessible surface on Hammett-type dependencies of infinite dilution 29Si and 13C NMR shifts in ring substituted silylated phenols dissolved in chloroform and acetone
Blechta, Vratislav,Sabata, Stanislav,Sykora, Jan,Hetflejs, Jiri,Soukupova, Ludmila,Schraml, Jan
experimental part, p. 128 - 134 (2012/08/07)
Infinite dilution 29Si and 13C NMR chemical shifts were determined from concentration dependencies of the shifts in dilute chloroform and acetone solutions of para substituted O-silylated phenols, 4-R-C6H4-O-SiR′2R″ (R = Me, MeO, H, F, Cl, NMe2, NH2, and CF3), where the silyl part included groups of different sizes: dimethylsilyl (R′ = Me, R″ = H), trimethylsilyl (R′ = R″ = Me), tert-butyldimethylsilyl (R′ = Me, R″ = CMe3), and tert-butyldiphenylsilyl (R′ = C6H5, R″ = CMe3). Dependencies of silicon and C-1 carbon chemical shifts on Hammett substituent constants are discussed. It is shown that the substituent sensitivity of these chemical shifts is reduced by association with chloroform, the reduction being proportional to the solvent accessible surface of the oxygen atom in the Si-O-C link. Copyright
Electron-Rich 0 = PR3 compounds: Catalysts for alcohol silylation
Liu, Xiaodong,Verkade, John G.
, p. 21 - 26 (2007/10/03)
The catalytic effect of a group of R3P = O compounds was studied in a mild procedure for the silylation of primary alcohols, secondary alcohols, hindered secondary alcohols, and of hindered phenols in the presence of t-butyldimethylsilyl chlori
Directed Lithiation of Chlorobenzenes. Regioselectivity and Application to a Short Synthesis of Benzocyclobutenes
Iwao, Masatomo
, p. 3622 - 3627 (2007/10/02)
Chlorobenzene and its OMe, OSiMe2-t-Bu, and Cl derivatives 1 were lithiated with high regioselectivity ortho to chlorine by treatment with sec-BuLi in THF at -105 deg C without complications due to benzyne formation.The lithio species thus generated under
