Efficient trimethylsilylation of alcohols and phenols in the presence of ZrCl4 as a reusable catalyst

Electron‐deficient vanadium(IV) tetraphenylporphyrin: A new, highly efficient and reusable catalyst for chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane

“…One disadvantage of HMDS is its poor silylating power in the absence of a suitable catalyst, needing forceful conditions and long reaction times in many cases. [10] To solve this problem, a variety of catalysts, including (CH 3 ) 3 SiCl, [11] ZrCl 4 , [12] ZnCl 2 , [13] K-10 montmorillonite, [14] LiClO 4 , [15] H 3 PW 12 O 40 , [16] iodine, [17] InBr 3 , [18] zirconium sulfophenyl phosphonate, [19] CuSO 4 .5H 2 O, [20] sulfonic acid-functionalized nanoporous silica, [21] MgBr 2 ·OEt 2 , [22] LaCl 3 , [23] poly(N-bromobenzene-1,3-disulfonamide) and N,N,N ,Ntetrabromobenzene-1,3-disulfonamide, [24] Fe(TFA) 3 , [25] Fe 3 O 4 , [26] (n-Bu 4 N)Br, [27] trichloroisocyanuric acid (TCCA), [28] HClO 4 -SiO 2 , [29] Pd [30] and ZrO(OTf) 2 , [31] have been reported for trimethylsilylation of alcohols and phenols. Although these procedures provide an improvement, many of the catalysts or activators need long reaction times, drastic reaction conditions or tedious workups, or are moisture-sensitive or expensive.…”

NaHSO4.H2O promoted oxidative deprotection of trimethylsilyl, tetrahydropyranyl and methoxymethyl ethers with HIO3

“…Trimethylsilyl, tetrahydropyranyl and methoxymethyl ethers were prepared according to the literature procedures. 16,17,[25][26][27] All oxidation products are known compounds; they are identified by comparison of their physical data, IR and NMR spectra with those of authentic samples. Yields refer to isolated products or their 2,4-dinitrophenylhydrazones.…”

Mild and efficient silylation of alcohols and phenols with HMDS using Bi(OTf)3 under solvent-free condition

“…Concentration of the organic layer under vacuum gave crude mass, which was purified by column chromatography with silica gel. 1 H and 13 C NMR data for known products are the same with literature values [8,14,[33][34][35][36]. Spectral data and HRMS values for new products are given below (entries 6, 7, 9, 11, 13-15, 18-22 and 26).…”