A mild and efficient method for the chemoselective trimethylsilylation of alcohols and phenols and deprotection of silyl ethers using sulfonic acid-functionalized ordered nanoporous Na+-montmorillonite
Source abstract
Abstract
Abstract Sulfonic acid-functionalized ordered nanoporous Na+-montmorillonite (SANM), is easily prepared by the reaction of Na+-montmorillonite with chlorosulfonic acid. This reagent acts as a highly efficient and reusable catalyst for the chemoselective trimethylsilylation of alcohols and phenols and deprotection of silyl ethers under mild and completely heterogeneous reaction conditions.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Chemical Synthesis and Reactions · Sulfur-Based Synthesis Techniques · Layered Double Hydroxides Synthesis and Applications
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (39)
Show source-provided references
1. Surface modification of clay minerals10.1016/S0169-1317(01)00063-1 ↗
2. The structure of montmorillonite. Preliminary communication on the ability of clays and clay minerals to be methylated
3. Catalysts for silylations with 1,1,1,3,3,3-hexamethyldisilazane10.1021/jo00141a031 ↗
4. Inorganic solid acids and their use in acid-catalyzed hydrocarbon reactions10.1021/cr00035a006 ↗
5. Silylation selective par l'hexamethyldisilazane10.1016/S0040-4039(00)96858-8 ↗
6. Heterogeneous catalysis in trimethylsilylation of alcohols and phenols by zirconium sulfophenyl phosphonate10.1080/00397919908085797 ↗
7. A simple and convenient method for cleavage of silyl esthers10.1080/00397919008052319 ↗
8. Organische derivate von tonmineralien10.1002/hlca.19500330514 ↗
9. Fieser · 1999
10. Deprotection and direct oxidative deprotection of trimethylsilyl ethers to their corresponding alcohols and carbonyl compounds with tris[trinitratocerium(IV)] paraperiodate, [(NO3)3Ce]3.H2IO6, in an aprotic solvent10.1080/00397919608003633 ↗
11. Firouzabadi · Journal of Organometallic Chemistry · 2008 · 693 · 271110.1016/j.jorganchem.2008.05.018 ↗
12. Highly regio- and chemoselective silylation of diethyl α-hydroxyphosphonates, alcohols and phenols in the presence of solid TiCl3(OTf) as a catalyst with hexamethyldisilazane (HMDS) at room temperature in the absence of solvent10.1016/j.catcom.2009.04.013 ↗
13. Poly(N-bromobenzene-1,3-disulfonamide) and N, N, N′, N′-tetrabromobenzene-1,3-disulfonamide as novel catalytic reagents for silylation of alcohols, phenols, and thiols using hexamethyldisilazane10.1016/j.tetlet.2006.03.157 ↗
14. Polymer-silica nanocomposites: model systems for confined polymers and polymer brushes
15. The clay minerals in soils10.1016/S0065-2113(08)60748-8 ↗
16. 1,3-Dibromo-5,5-diethylbarbituric acid as an efficient catalyst for the protection of various alcohols with HMDS under solvent-free conditions10.1016/j.catcom.2006.07.012 ↗
17. Trichloroisocyanuric acid (TCCA) as a mild and efficient catalyst for the trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) under heterogonous conditions10.1016/j.catcom.2006.06.018 ↗
18. Chemical reactions on clays10.1126/science.235.4795.1473 ↗
19. Solubility of ethylene in 2,2,4-trimethylpentane and 1-octene mixture
20. Dimerisation of olefins catalysed by K10-montmorillonite clays10.1023/A:1009030413003 ↗
21. Lanthanum trichloride: an efficient catalyst for the silylation of hydroxyl groups by activating hexamethyldisilazane (HMDS)10.1016/j.jorganchem.2007.05.002 ↗
22. Facile O-silylation of tertiary alcohols in the presence of Mg-metal
23. Perfluorinated resinsulfonic acid (Nafion-H®) catalysis in synthesis10.1055/s-1986-31692 ↗
24. Aromatic substitution. 43. Perfluorinated resinsulfonic acid catalyzed nitration of aromatics10.1021/jo00418a019 ↗
25. Nafion® SAC-13: heterogeneous and reusable catalyst for the activation of HMDS for efficient and selective O-silylation reactions under solvent-free condition10.1016/j.tet.2009.04.025 ↗
26. Interfacial effects on the reinforcement properties of polymer−organoclay nanocomposites10.1021/cm960227m ↗
27. Efficient trimethylsilylation of alcohols and phenols in the presence of ZrCl4 as a reusable catalyst10.1016/j.catcom.2006.11.015 ↗
28. Silylation and tetrahydropyranylation of alcohols catalyzed by Al(HSO4)310.1246/bcsj.78.1982 ↗
29. Efficient trimethylsilylation and tetrahydropyranylation of alcohols in the presence of 1,3-Dibromo-5,5-dimethylhydantoin10.1055/s-2006-950350 ↗
30. Fe(HSO4)3 Promoted trimethylsilylation of alcohols and phenols in solution and under solvent-free conditions10.1007/s00706-007-0695-1 ↗
31. Solvent free selective silylation of alcohols, phenols and naphthols with HMDS catalyzed by H-β zeolite10.3998/ark.5550190.0005.e08 ↗
32. Silylation of 1,3-dicarbonyl compounds with hexamethyldisilizane and imidazole10.1055/s-1976-24171 ↗
33. Preparation and catalytic properties of cationic and anionic clays10.1016/S0920-5861(98)00038-8 ↗
34. N,N′-Bis[trimethylsilyl]-urea: a useful silylating agent for alcohols and carboxylic acids10.1055/s-1981-29605 ↗
35. Preparation of highly exfoliated epoxy/clay nanocomposites by “Slurry Compounding”: process and mechanisms10.1021/la047709u ↗
36. Mild base mediated desilylation of various phenolic silyl ethers10.1016/S0040-4039(96)02270-8 ↗
37. Yariv · 2002
38. A novel and highly efficient method for the silylation of alcohols with hexamethyldisilazane (HMDS) catalyzed by recyclable sulfonic acid-functionalized ordered nanoporous silica10.1016/j.tetlet.2006.12.030 ↗
39. Montmorillonite clay catalysis XI1: protection and deprotection of hydroxyl group by formation and cleavage of trimethylsilyl ethers catalysed by montmorillonite K-1010.1080/00397919808004891 ↗