- Zinc chloride catalyzed silylation of alcohols and phenols by hexamethyldisilazane. A highly chemoselective reaction
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Hexamethyldisilazane (HMDS) in presence of a catalytic amount of anhydrous zinc chloride silylates efficiently and selectively different types of alcohols and phenols in refluxing acetonitrile or benzene-acetonitrile. This reagent in presence of anhydrous
- Firouzabadi,Karimi
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Read Online
- An asymmetric Salamo-based Zn complex supported on Fe3O4MNPs: a novel heterogeneous nanocatalyst for the silyl protection and deprotection of alcohols under mild conditions
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In this study, a magnetic asymmetric Salamo-based Zn complex (H2L = salen type di-Schiff bases)-supported on the surface of modified Fe3O4(Fe3O4@H2L-Zn) as a new catalyst was designed and characterizedvianumerous analytical techniques such as FT-IR spectroscopy, XRD, EDS, ICP-AES, SEM, TEM, TGA and VSM. An efficient and sustainable synthetic protocol has been presented for the synthesis of silyl ether substructuresviathe silyl protection of alcohols under mild conditions. The synthetic protocol involves a two-component solvent-free reaction between various hydroxyl-bearing substrates and hexamethyldisilazane (HMDS) as an inexpensive silylating agent using Fe3O4@H2L-Zn MNPs as a magnetically separable, recyclable and reusable heterogeneous catalyst. Fe3O4@H2L-Zn MNPs were also applied for the removal of silyl protecting groups from hydroxyl functions using water in CH2Cl2under green conditions. The catalyst demonstrated good to excellent catalytic yield efficiency for both the reactions compared to the commercial metal-based catalysts under green conditions for a wide range of substrates.
- Yao, Hongyan,Wang, Yongsheng,Razi, Maryam Kargar
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p. 12614 - 12625
(2021/04/14)
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- Nanoporous Na+-montmorillonite perchloric acid as an efficient and recyclable catalyst for the chemoselective protection of hydroxyl groups
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Nanoporous Na+-montmorillonite perchloric acid as a novel heterogeneous reusable solid acid catalyst was easily prepared by treatment of Na+-montmorillonite as a cheap and commercially available support with perchloric acid. The catalyst was characterized using a variety of techniques including X-ray powder diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), thermogravimetric analysis (TGA), energy dispersive X-ray spectroscopy (EDX), pH analysis and determination of the Hammett acidity function. The prepared reagent showed excellent catalytic activity for the chemoselective conversion of alcohols and phenols to their corresponding trimethylsilyl ethers with 1,1,1,3,3,3-hexamethyldisilazane (HMDS) at room temperature. Deprotection of the resulting trimethylsilyl ethers can also be carried out using the same catalyst in ethanol. All reactions were performed under mild and completely heterogeneous reaction conditions in good to excellent yields. The notable advantages of this protocol are: short reaction times, high yields, availability and low cost of the reagent, easy work-up procedure and the reusability of the catalyst during a simple filtration.
- Mashhadinezhad, Maryam,Shirini, Farhad,Mamaghani, Manouchehr
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p. 2099 - 2107
(2019/01/03)
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- Fast and efficient method for Silylation of alcohols and phenols with HMDS in the presence of bis-thiourea complexes of cobalt, nickel, copper and zinc chlorides
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Bis-thiourea complexes of cobalt, nickel, copper and zinc chlorides were used efficiently for rapid and efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) in CH3CN. All reactions were carried out at room temperature within immediate-120?min timeframe to afford trimethylsilyl ether derivatives in high to excellent yields. Investigation of the results exhibited that the prepared bis-thiourea metal complexes show the activity as Co(tu)2Cl2> Ni(tu)2Cl2> Cu(tu)2Cl2> Zn(tu)2Cl2 in their silylation reactions.
- Zeynizadeh, Behzad,Sorkhabi, Serve
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p. 127 - 135
(2018/02/06)
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- Benzyltriboronates: Building Blocks for Diastereoselective Carbon-Carbon Bond Formation
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A highly diastereoselective carbon-carbon bond-forming reaction involving the tandem coupling of benzyltriboronates, enoates, and alkyl halides is described. This method was enabled by the discovery of α-diimine nickel catalysts that promote the chemosele
- Palmer, W. Neil,Zarate, Cayetana,Chirik, Paul J.
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supporting information
p. 2589 - 2592
(2017/03/01)
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- Introduction of PEG-SANM nanocomposite as a new and highly efficient reagent for the promotion of the silylation of alcohols and phenols and deprotection of the silyl ethers
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Poly (ethylene glycol)-sulfonated sodium montmorillonite (PEG-SANM) nanocomposite was prepared by a simple method and characterized using XRD, TGA, SEM, TEM, and FT-IR techniques. After preparation and characterization, this reagent was used as a highly efficient and reusable solid acid catalyst for the chemoselective silylation of alcohols and phenols and deprotection of the obtained silyl ethers. Themethod offers several advantages including high to excellent yields of the products, short reaction times, easy preparation of the catalyst and easy work-up procedure. In addition, the catalyst can be recycled and reused at least for five times without significant decrease in the catalytic activity.
- Shirini, Farhad,Shojaei, Abdollah Fallah,Heirati, Seyedeh Zahra Dalil
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p. 944 - 951
(2016/07/06)
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- Selective silylation of alcohols, phenols and oximes using N-chlorosaccharin as an efficient catalyst under mild and solvent-free conditions
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Efficient silylation of OH group in alcohols, phenols and oximes is described using a catalytic amount of N-chlorosaccharin and hexamethyldisilazane (HMDS) under mild and solvent-free conditions. This silylation reaction can be carried out with excellent and interesting various selectivities.
- Aghapour, Ghasem,Moghaddam, Ali Kazemi,Nadali, Samaneh
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p. 197 - 203
(2015/05/12)
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- Introduction of a New Ionic Liquid Catalyst for the Trimethylsilyl and Tetrahydropyranyl Protection of Alcohols
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1,1'-Disulfo-[2,2'-bipyridine]-1,1'-hydrogen sulfate, BiPy(SO3H)2(HSO4)2, is prepared and identified as a new ionic liquid. This reagent was used for the promotion of the chemoselective trimethylsilyl and tetrahydropyranyl protection of alcohols. All reactions were performed under mild reaction conditions in high to excellent yields. Ease of the preparation of the heterogeneous catalyst, simplicity and easy work-up procedure, high reaction rates, and recyclability and reusability of the catalyst are the main advantages of this method.
- Shirini, Farhad,Abedini, Masoumeh,Mahmoodi, Nosratollah,Biglari, Mohammad,Safarpoor Nikoo Langrudi, Mohaddeseh
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p. 1912 - 1921
(2015/12/12)
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- Highly efficient protection of alcohols and phenols catalysed by tin porphyrin supported on MIL-101
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The catalytic activity of 5,10,15,20-tetrakis(4-aminophenyl)porphyrinatotin(IV) trifluoromethanesulfonate, [SnIV(TNH2PP)(OTf)2], supported on chloromethylated MIL-101, was investigated in the trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) and also their tetrahydropyranylation with 3,4-dihydro-2H-pyran. Excellent yields, mild reaction conditions, short reaction times and reusability of the catalyst without significant decrease in its initial activity are noteworthy advantages of this supported catalyst.
- Zadehahmadi, Farnaz,Tangestaninejad, Shahram,Moghadam, Majid,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj,Kardanpour, Reihaneh
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p. 209 - 215
(2015/03/30)
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- Polystyrene-gallium trichloride complex: A mild, highly efficient, and recyclable polymeric lewis acid catalyst for chemoselective silylation of alcohols and phenols with hexamethyldisilazane
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Polystyrene-supported gallium trichloride (PS/GaCl3) as a highly active and reusable heterogeneous Lewis acid effectively activates hexamethyldisilazane (HMDS) for the efficient silylation of alcohols and phenols at room temperature. In this he
- Rahmatpour, Ali,Vakili, Ali,Azizian, Setare
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p. 443 - 451
(2013/12/04)
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- Preparation, characterization and use of 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient, halogen-free and reusable ionic liquid catalyst for the trimethylsilyl protection of hydroxyl groups and deprotection of the obtained trimethylsilanes
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Novel 1,3-disulfonic acid imidazolium hydrogen sulfate, a halogen-free ionic liquid, is a recyclable and eco-benign catalyst for the trimethylsilyl protection of hydroxyl groups at room temperature under solvent free conditions to afford trimethylsilanes in excellent yields (92-100%) and in very short reaction times (1-5 min). Deprotection of the resulting trimethylsilanes can also be achieved using the same catalyst in methanol. The catalyst was characterized by IR, 1H NMR, 13C NMR and MS studies. All the products were extensively characterized by IR, 1H NMR, MS, and elemental and melting point analyses. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be recovered and reused for several times without loss of activity. The work-up of the reaction consists of a simple separation, followed by concentration of the crude product and purification.
- Shirini, Farhad,Khaligh, Nader Ghaffari,Akbari-Dadamahaleh, Somayeh
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- Nanocrystalline TiO2-HClO4 as a new, efficient and recyclable catalyst for the chemoselective trimethylsilylation of alcohols, phenols and deprotection of silyl ethers
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TiO2-HClO4, as a new solid acid, was found to be an efficient catalyst for the chemoselective trimethylsilylation of alcohols and phenols. Deprotection of the resulting trimethylsilylethers was achieved using the same catalyst in methanol solvent. The synthesized catalyst was characterized by FT-IR, SEM, TEM, BET and XRD analyses. Our novel synthetic method has the advantages of high yields, short reaction times, low cost and recyclability of the catalyst, simplicity and easy work-up compared to the conventional methods reported in the literature.
- Shirini, Farhad,Atghia, Seyyed Vahid,Jirdehi, Mojtaba Ghazi
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- Cu(NO3)2 · 3 H2O as an efficient reagent for the chemoselective trimethylsilylation of primary alcohols and oxidation of trimethylsilyl ethers
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Cu(NO3)2 · 3 H2O can be used as an efficient reagent for the chemoselective trimethylsilylation of primary benzylic and aliphatic alcohols with hexamethyldisilazane (HMDS). This reagent is also able to oxidize the obtained trimethylsilyl ethers to the corresponding carbonyl compounds in the presence of wet SiO2 and KBr. In this study, all reactions are performed in the absence of a solvent and good-to-high yields are obtained.
- Shirini,Mashhadi-Nejad
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experimental part
p. 376 - 381
(2012/04/04)
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- Highly efficient and chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalyzed by reusable electron-deficient [TiIV(salophen)(OTf)2]
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In the present work, highly efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalyzed by high-valent [Ti IV(salophen)(OTf)2] is reported. Under these conditions, primary, secondary and tertiary alcohols as well as phenols were silylated in short reaction times and high yields. It is noteworthy that this method can be used for chemoselective silylation of primary alcohols in the presence of secondary and tertiary alcohols and phenols. The catalyst was reused several times without loss of its catalytic activity.
- Yadegari, Maryam,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj
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experimental part
p. 332 - 338
(2012/03/12)
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- Highly efficient and selective trimethylsilylation of alcohols and phenols with hexamethyldisilazane catalyzed by polystyrene-bound tin(IV) porphyrin
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In the present work, investigation of the catalytic activity of tetrakis(p-aminophenyl)porphyrinatotin(IV) trifluoromethanesulfonate, [Sn IV(TNH2PP)(OTf)2], supported on chloromethylated polystyrene in the trimethylsilylation of alcohols and phenols with hexamethyldisilazane is reported. The prepared catalyst was characterized by elemental analysis, FT-IR and diffuses reflectance UV-Vis spectroscopic methods. This catalyst was used for selective trimethylsilylation of different alcohols and phenols with HMDS, with short reaction times and high yields. Also the catalyst is of high reusability and stability, in that it was recovered several times without loss of its initial activity.
- Gharaati, Shadab,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj
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experimental part
p. 87 - 95
(2012/05/05)
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- Preparation, characterization and use of 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate as an eco-benign, efficient and reusable ionic liquid catalyst for the chemoselective trimethylsilyl protection of hydroxyl groups
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New and novel ionic liquid (3-methyl-1-sulfonic acid imidazolium hydrogen sulfate) is a recyclable and eco-benign catalyst for the chemoselective trimethylsilyl protection of hydroxyl groups under solvent-free conditions to afford trimethylsilanes in excellent yields (92-100%) and in very short reaction times (1-8 min). The catalyst was characterized by FT-IR, 1H NMR and 13C NMR studies. All the products were extensively characterized by 1H NMR, IR, GC-MS and melting point analyses. A mechanism for the catalytic activity is proposed. The catalyst can be recovered and reused without loss of activity. The work-up of the reaction consists of a simple separation, followed by concentration of the crude product and purification.
- Khaligh, Nader Ghaffari
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experimental part
p. 63 - 70
(2011/12/02)
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- Succinimide-N-sulfonic acid: A mild, efficient, and reusable catalyst for the chemoselective trimethylsilylation of alcohols and phenols
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Succinimide-N-sulfonic acid (SuSA) is easily prepared by the reaction of succinimide with chlorosulfonic acid. This reagent is able to efficiently catalyze the chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS). All reactions were performed under mild reaction conditions, giving excellent yields. Copyright Taylor & Francis Group, LLC.
- Shirini,Khaligh, Nader Ghaffari
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experimental part
p. 2156 - 2165
(2012/04/10)
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- Trimethylsilyl protection of alcohols over phosphorus pentoxide supported on silica gel
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An eco-friendly and mild protocol for trimethylsilyl protection of alcohols over phosphorus pentoxide supported on silica gel using hexamethyldisilazane has been described. Solvent-free and ambient reaction conditions, easy workup, short reaction times, e
- Shaterian, Hamid Reza,Fahimi, Nafiseh,Azizi, Kobra
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experimental part
p. 1604 - 1611
(2011/10/05)
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- Rapid and highly efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalysed by in situ generated I2 using Oxone /KI or cerium ammonium nitrate (CAN)/KI systems under mild conditions
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Structurally diverse alcohols and phenols were trimethylsilylated in clean and efficient reactions with hexamethyldisilazane (HMDS) in the presence of a catalytic amount of I2 generated in situ from Oxone /KI or CAN/KI systems. The reactions occur rapidly in good to high yields in wet CH2Cl2 at room temperature. Indian Academy of Sciences.
- Kolvari, Eskandar,Khazaei, Ardeshir,Zolfigol, Mohammad Ali,Koukabi, Nadiya,Gilandoust, Maryam,Bakhit, Neda
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experimental part
p. 703 - 708
(2012/07/14)
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- Electron-deficient vanadium(IV) tetraphenylporphyrin: A new, highly efficient and reusable catalyst for chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane
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In the present work, the application of electron-deficient tetraphenylporphyrinatovanadium(IV) trifluoromethanesulfonate, [V IV(TPP)(OTf)2], in the trimethylsilylation of alcohols and phenols with hexamethydisilazane (HMDS) is reported. This new V(IV) catalyst was used as an efficient catalyst for silylation of not only primary alcohols but also sterically hindered secondary and tertiary alcohols with HMDS. Trimethylsilylation of phenols with HMDS was also performed to afford the desired Trimethylsilyl ethers (TMS) ethers. The chemoselectivity of this method was also investigated. This catalyst can be reused several times without loss of its activity. Copyright
- Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Tangestaninejad, Shahram,Mirkhani, Valiollah,Khosropour, Ahmad Reza,Taghavi, S. Abdolmanaf
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experimental part
p. 687 - 694
(2012/01/06)
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- A new crystal engineering approach for the synthesis of {[K.18-Crown-6]I3}n as a nanotube-like and recyclable catalyst for the chemoselective silylation of alcohols
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Reaction of 18-crown-6 with KI in ethanol solution followed by addition of iodine (I2) afforded a unique triiodide salt with a nanotube-like structure ({[K.18-Crown-6]I3}n). It is shown that this reagent may be used for the chemoselective trimethylsilylation of alcohols. The synthesis of the crystalline reagent is a good example of crystal engineering. Reagent was recycled and reused.
- Zolfigol,Kolvari,Koukabi,Salehzadeh,Chehardoli,Tidmarsh,Niknam
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experimental part
p. 484 - 494
(2012/06/18)
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- Rapid and efficient protection of alcohols and phenols, and deprotection of trimethylsilyl ethers catalyzed by a cerium-containing polyoxometalate
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Herein, we want to report a simple and convenient way for protection-deprotection of alcohols in the presence of ammonium decatungstocerate(IV) {(NH4)8[CeW10O 36]A·20H2O} as catalyst under ambient temperature in CH3CN. Using 0.002 mmol of the catalyst, various alcohols and phenols were transformed easily to the corresponding TMS ethers in excellent yields. In the second part, various TMS ethers were successfully converted to the parent hydroxyl compounds in the presence of the ammonium decatungstocerate(IV) catalyst.
- Yadollahi, Bahram,Mirkhani, Valiollah,Tangestaninejad, Shahram,Karimian, Davud
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experimental part
p. 83 - 86
(2012/06/18)
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- Sulfated zirconia: An efficient catalyst for solvent-free synthesis of silyl ethers under mild conditions
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Oximes, allylic, aliphatic, aromatic, cyclic, acyclic, and hetero alcohols are silylated in short reaction times with good yields in the midst of a catalytic amount of sulfated zirconia solid acid catalyst and trimethylsilyl cyanide under nonbasic, solvent-free, and ambient temperature conditions. Selectivity toward O-silyl ether rather than N-silyl ether has been observed. This simple experimental procedure, combined with easy recovery and reusability of the catalyst, is expected to contribute to the development of a clean and environmentally friendly strategy for the synthesis of O-silyl ethers. Copyright
- Thirupathi, Boningari,Prasad, Avvari N.,Srinivas, Rapelli,Reddy, Benjaram M.
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experimental part
p. 2064 - 2072
(2011/07/30)
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- Silica-bonded S-sulfonic acid as a recyclable catalyst for the silylation of hydroxyl groups with hexamethyldisilazane (HMDS)
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Silica-bonded S-sulfonic acid (SBSSA) was prepared by the reaction of 3-mercaptopropylsilica (MPS) and chlorosulfonic acid in tert-butylmethyl ether, and used as a catalyst for the silylation of hydroxyl groups. A good range of primary, secondary alcohols
- Niknam, Khodabakhsh,Saberi, Dariush,Molaee, Hajar,Zolfigol, Mohammad Ali
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experimental part
p. 164 - 171
(2010/04/04)
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- H5IO6/KI: A new combination reagent for iodination of aromatic amines, and trimethylsilylation of alcohols and phenols through in situ generation of iodine under mild conditions
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A simple method for the in situ generation of iodine using H 5IO6/KI has been developed, and its application in silylation of OH group and iodination of aromatic amines is described.
- Zolfigol, Mohammad Ali,Khazaei, Ardeshir,Kolvari, Eskandar,Koukabi, Nadiya,Soltani, Hamid,Behjunia, Maryam
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experimental part
p. 587 - 594
(2010/06/14)
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- (PhCH2PPh3)+Br3-: A versatile reagent for the preparation, deprotection, and oxidation of trimethylsilyl ethers
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Benzyltriphenylphosphonium tribromide (BTPTB), as a stable solid reagent, is easily prepared by the reaction of benzyltriphenylphosphonium bromide with Br2. This reagent can be used as an efficient catalyst for the conversion of alcohols to their corresponding trimethylsilyl ethers (TMS ethers) with hexamethyldisilazane (HMDS). Desilylation of TMS ethers is also catalyzed by BTPTB in MeOH at room temperature in high yields. BTPTB is also able to oxidize the TMS ethers to their corresponding carbonyl compounds in a mixture of MeOH/H2O in good to high yields. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
- Shirini,Imanzadeh,Mousazadeh,Mohammadpoor-Baltork,Aliakbar,Abedini
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experimental part
p. 641 - 646
(2010/06/17)
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- [SnIV(TPP)(BF4)2]: An efficient and reusable catalyst for chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane
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Tin(IV)tetraphenylporphyrinato tetrafluoroborate, [SnIV(TPP)(BF4)2], was used as an efficient catalyst for trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS). High-valent [SnIV(TPP)(BF4)2] catalyzes trimethylsilylation of primary, secondary and tertiary alcohols as well as phenols, and the corresponding TMS-ethers were obtained in high yields and short reaction times at room temperature. While, under the same reaction conditions [SnIV(TPP)Cl2] is less efficient to catalyze these reactions. One important feature of this catalyst is its ability in the chemoselective silylation of primary alcohols in the presence of secondary and tertiary alcohols and phenols. The catalyst was reused several times without loss of its catalytic activity.
- Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj,Gharaati, Shadab
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experimental part
p. 212 - 219
(2010/04/04)
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- Homolytic reactions of N-bromohexamethyldisilazane with trialkyl(phenylalkoxy) derivatives of silicon and tin
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The main product of the photoinduced reaction of N- bromohexamethyldisilazane with trialkyl-(benzyloxy)derivatives of silicon and tin R3MO(CH2)nPh (R = Me, Et; M = Si, Sn; n = 1) is N,N-dibenzylidene-C-phenylmethanediamine (hydrobenzamide). For M = Si, with increase of the length of the methylene chain between the oxygen atom and the phenyl group (n = 2, 3), the similar reaction affords the product of bromination of the benzylic carbon atom R3MO(CH2) n-1CHBrPh. For M = Sn, the reaction results in the formation of 2-phenyloxacycloalkanes PhCHO(CH2)n-1. Pleiades Publishing, Ltd., 2010.
- Rakhlin,Podgorbunskaya,Voronkov
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experimental part
p. 930 - 935
(2011/01/09)
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- Novel and highly efficient protection of aliphatic alcohols and phenols with hexamethyldisilazane in the presence of La(NO3) 3·6H2O
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Aliphatic alcohols and phenols are protected with hexamethyldisilazane in the presence of lanthanum nitrate hexahydrate (La(NO3) 3·6H2O) in excellent yields at room temperature. Taylor & Francis Group, LLC.
- Akhlaghinia, Batool
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experimental part
p. 2530 - 2535
(2010/03/31)
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- Highly efficient chemo- and regioselective silylation of -OH groups and cyanosilylation of aldehydes promoted by TiCl2(OTf)-SiO2 as a new recyclable catalyst
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TiCl2(OTf)-SiO2 as an easy handling recyclable catalyst was applied for trimethylsilylation of diethyl α-hydroxyphosphonates, alcohols and phenols with high selectivity using HMDS as a silylating agent. Cyanotrimethylsilyl ethers were also obtained in excellent yields from treatment of aldehydes with TMSCN in the presence of this catalyst.
- Firouzabadi, Habib,Iranpoor, Nasser,Farahi, Soghra
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scheme or table
p. 3923 - 3928
(2010/02/28)
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- Chemoselective trimethylsilylation of alcohols catalyzed by saccharin sulfonic acid
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Saccharin sulfonic acid was easily prepared by the reaction of saccharin with neat chlorosulfonic acid at room temperature. This reagent is efficiently able to catalyze the chemoselective trimethylsilylation of alcohols with hexamethyldisilazane in the pr
- Shirini, Farhad,Zolfigol, Mohammad Ali,Abedini, Masoumeh
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experimental part
p. 61 - 64
(2010/03/26)
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- Preparation of silica supported tin chloride: As a recyclable catalyst for the silylation of hydroxyl groups with HMDS
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Silica-supported tin chloride [SiO2-Sn(Cl)4-n] has been prepared by mixing tin chloride with activated silica gel in toluene under refluxing conditions for one day. Arange of primary, secondary, and tertiary alcohols as well as phenolic hydroxyl groups were converted into their corresponding trimethylsilyl ethers with hexamethyldisilazane in the presence of catalytic amounts of silica-supported tin chloride at room temperature. An excellent chemoselective silylation of hydroxyl groups in the presence of other functional groups was also observed. This catalyst could be recycled and reused fifteen times without loss of efficiency.
- Niknam, Khodabakhsh,Zolfigol, Mohammad Ali,Saberi, Dariush,Molaee, Hajar
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experimental part
p. 1257 - 1264
(2010/08/19)
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- Fe(HSO4)3 promoted trimethylsilylation of alcohols and phenols in solution and under solvent-free conditions
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Alcohols and phenols are efficiently converted to their corresponding trimethylsilyl ethers with hexamethyldisilazane (HMDS) in the presence of Fe(HSO4)3 in solution and under solvent-free conditions.
- Shirini, Farhad,Zolfigol, Mohammad A.,Abri, Abdol-Reza
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- Vanadium hydrogen sulfate (I): Chemoselective trimethylsilylation of alcohols and deprotection of trimethylsilyl ethers
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Trimethylsilylation of alcohols with hexamethyldisilazane (HMDS) catalyzed by V(HSO4)3 under mild and completely heterogeneous reaction condition is reported. The method is highly chemoselective for the protection of alcohols in the presence of phenols, amines and thiols. Also, the deprotection of trimethylsilyl ethers is performed in the presence of V(HSO 4)3 at room temperature in good to high yields.
- Shirini, Farhad,Zolfigol, Mohammad Ali,Abedini, Masoumeh,Sakhaei, Ali Reza
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experimental part
p. 943 - 946
(2009/12/24)
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- Silica triflate as a new, efficient, and reusable reagent for the chemoselective silylation of alcohols and phenols and deprotection of silyl ethers
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Silica triflate was easily prepared via reaction of silica gel and trifluoromethane sulfonyl chloride at room temperature. This compound can be employed as an efficient and reusable reagent for the chemoselective silylation of alcohols and phenols in solution and under solvent-free conditions. This reagent also effectively catalyzed the deprotection of silyl ethers in refluxing methanol.
- Shirini,Marjani,Nahzomi, H. Taherpour,Zolfigol
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p. 168 - 177
(2008/12/22)
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- Rapid and highly efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalyzed by reusable zirconyl triflate, [ZrO(OTf)2]
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In this paper, rapid and efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane in the presence of catalytic amounts of ZrO(OTf)2 is reported. Primary, secondary and tertiary alcohols as well as phenols were efficiently converted to their corresponding TMS ethers in short reaction times at room temperature. It is noteworthy that this method can be used for chemoselective silylation of primary alcohols in the presence of secondary and tertiary alcohols and phenols.
- Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj,Chahardahcheric, Shahin,Tavakoli, Ziba
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p. 2041 - 2046
(2008/09/19)
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- An efficient organocatalyzed interconversion of silyl ethers to tosylates using DBU and p-toluenesulfonyl fluoride
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A mild and efficient interconversion from silyl ethers to sulfonates esters is reported with good yields. This silyl-sulfonyl exchange proceeds readily in acetonitrile at room temperature in the presence of p-toluenesulfonyl fluoride and a catalytic amount of 1,8-diazabicyclo[5.4.0]undec-7ene (DBU). This method can be used with trimethysilyl (TMS), triethylsilyl (TES) and tert-butyldimethylsilyl (TBDMS) ethers. Georg Thieme Verlag Stuttgart.
- Gembus, Vincent,Marsais, Francis,Levacher, Vincent
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experimental part
p. 1463 - 1466
(2009/04/07)
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- A new and efficient method for the protection of alcohols and phenols by using hexamethyldisilazane in the presence of anhydrous ferric chloride under mild reaction conditions
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Alcohols and phenols are protected with hexamethyldisilazane in the presence of anhydrous ferric chloride in good to excellent yields in acetonitrile. This method is highly selective for the conversion of primary alcohols in the presence of secondary and
- Akhlaghinia, Batool
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p. 687 - 694
(2008/02/04)
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- Lanthanum trichloride: An efficient catalyst for the silylation of hydroxyl groups by activating hexamethyldisilazane (HMDS)
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A variety of hydroxy functional groups was protected as their corresponding trimethylsilyl ethers using HMDS in the presence of lanthanum trichloride. The catalyst LaCl3 activates the HMDS and accelerates the reaction under mild reaction conditions at room temperature to afford the corresponding silylated products in excellent yields.
- Narsaiah, Akkirala Venkat
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p. 3614 - 3618
(2008/02/08)
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- A novel and highly efficient method for the silylation of alcohols with hexamethyldisilazane (HMDS) catalyzed by recyclable sulfonic acid-functionalized ordered nanoporous silica
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Silylation of alcohols with hexamethyldisilazane (HMDS) in dichloromethane provides the corresponding silyl ethers in almost quantitative yields at room temperature using 1-3 mol % of sulfonic acid-functionalized silica. Additionally, the catalyst display
- Zareyee, Daryoush,Karimi, Babak
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p. 1277 - 1280
(2007/10/03)
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- Efficient trimethylsilylation and tetrahydropyranylation of alcohols in the presence of 1,3-dibromo-5,5-dimethylhydantoin
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Chemoselective trimethylsilylation and tetrahydropyranylation of benzylic and primary and secondary aliphatic alcohols proceed efficiently in the presence of 1,3-dibromo-5,5-dimethylhydantoin (DBH) under mild and completely heterogeneous reaction conditio
- Shirini, Farhad,Zolfigol, Mohammad Ali,Paktinat, Maryam
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p. 4252 - 4256
(2008/03/27)
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- Trimethylsilylation of alcohols and phenols using KBr as an efficient and reusable catalyst
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KBr acts as an efficient and reusable catalyst for the selective and efficient trimethylsilylation of benzylic, primary and secondary aliphatic alcohols and phenols with hexamethyldisilazane. All reactions were performed at room temperature under mild and
- Shirini, Farhad,Mollarazi, Esmail
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p. 1109 - 1115
(2007/10/03)
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- Indium tribromide: An efficient catalyst for the silylation of hydroxy groups by the activation of hexamethyldisilazane
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A variety of substrates containing hydroxy groups have been protected as their corresponding trimethylsilyl ethers using 1,1,1,3,3,3-hexamethyldisilazane in the presence of indium tribromide. The catalyst indium tribromide activates the 1,1,1,3,3,3-hexamethyldisilazane and accelerates the reaction under mild reaction conditions at room temperature. Georg Thieme Verlag Stuttgart.
- Yadav,Reddy,Basak,Baishya,Venkat Narsaiah
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p. 3831 - 3834
(2008/02/10)
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- A novel efficient method for the silylation of alcohols using hexamethyldisilazane in an ionic liquid
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Benzylic and primary alcohols were protected by hexamethyldisilazane in good to excellent yields at r.t. in 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF4]) ionic liquid. In addition, the ionic liquid was recovered quantitatively and reused efficiently in the next reactions. The protocol was successfully applied to the protection of phenols. Copyright Taylor & Francis Group, LLC.
- Mojtahedi, Mohammad M.,Abbasi, Hassan,Abaee, M. Saeed
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p. 1541 - 1544
(2007/10/03)
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- An efficient method for the protection of alcohols and phenols by using hexamethyldisilazane in the presence of cupric sulfate pentahydrate under neutral reaction conditions
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Alcohols and phenols are protected with hexamethyldisilazane in the presence of cupric sulfate pentahydrate in good to excellent yields in acetonitrile. The method is highly selective for the conversion of primary alcohols in the presence of secondary and tertiary alcohols as well as phenols. Georg Thieme Verlag Stuttgart.
- Akhlaghinia, Batool,Tavakoli, Sedigheh
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p. 1775 - 1778
(2007/10/03)
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- Aluminium triflate [Al(OTf)3] as a recyclable catalyst for the conversion of α-hydroxyphosphonates, alcohols and phenols to their corresponding O-silylated products with hexamethyldisilazane (HMDS)
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Al(OTf)3 as a recyclable catalyst conducts the efficient conversion of various types of α-hydroxyphosphonates to their corresponding α-trimethysilyloxyphosphonates with HMDS in the absence of solvent at room temperature. The general applicabili
- Firouzabadi, Habib,Iranpoor, Nasser,Sobhani, Sara,Ghassamipour, Soheila
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p. 595 - 599
(2007/10/03)
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- Silylation and tetrahydropyranylation of alcohols catalyzed by Al(HSO 4)3
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Trimethylsilylation and tetrahydropyranylation of alcohols are efficiently catalyzed by Al(HSO4)3. All reactions were performed under mild and completely heterogeneous conditions in good-to-high yields.
- Shirini, Farhad,Zolfigol, Mohammad Ali,Abedini, Masoumeh
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p. 1982 - 1985
(2007/10/03)
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- Al(HSO4)3 as an efficient reagent for the selective trimethylsilylation of primary alcohols under solvent-free conditions
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Primary alcohols are selectively trimethylsilylated using Hexamethyldisilazane (HMDS) in the presence of a catalytic amount of Al(HSO 4)3 under solvent free conditions. Copyright Taylor & Francis Inc.
- Shirini, Farhad,Zolfigol, Mohammad Ali,Abedini, Masoumeh
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p. 2299 - 2302
(2007/10/03)
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- Magnesium triflate [Mg(OTf)2] a highly stable, non-hygroscopic and a recyclable catalyst for the high yielding preparation of diethyl α-trimethylsilyloxyphosphonates from diethyl α-hydroxyphosphonates by HMDS under solventless conditions
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A broad, adaptable, high yielding and convenient procedure for the easy conversion of various α-hydroxyphosphonates to α-trimethylsilyloxyphosphonates under mild conditions with HMDS in the presence of a catalytic amount of magnesium triflate as a highly stable and a non-hygroscopic recyclable catalyst in neat conditions is described. In order to show the general applicability of this method, we have also applied this procedure successfully for the silylation of ordinary alcohols and phenols.
- Firouzabadi, Habib,Iranpoor, Nasser,Sobhani, Sara,Ghassamipour, Soheila
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p. 3197 - 3202
(2007/10/03)
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- Copper triflate [Cu(OTf)2] is an efficient and mild catalyst for the silylation of α-hydroxyphosphonates to α-trimethylsilyloxyphosphonates with HMDS at room temperature
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A broad, adaptable, high yielding and convenient procedure for the fast conversion of various α-hydroxyphosphonates to α-trimethylsilyloxyphosphonates under mild conditions with HMDS in the presence of a catalytic amount of copper triflate is described. T
- Firouzabadi, Habib,Iranpoor, Nasser,Sobhani, Sara,Ghassamipour, Soheila,Amoozgar, Zohreh
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p. 891 - 893
(2007/10/03)
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- A mild and efficient method for chemoselective silylation of alcohols using hexamethyldisilazane in the presence of silica chloride
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Reaction of alcohols with hexamethyldisilazane in the presence of silica chloride provides efficiently the corresponding trimethylsilyl ethers. This system discriminates absolutely amines and thiols from alcohols.
- Shirini, Farhad,Zolfigol, Mohammad Ali,Mohammadi, Kamal
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p. 1567 - 1570
(2007/10/03)
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