- KF/clinoptilolite NPs: An efficient and heterogeneous catalyst for chemoselective silylation of alcohols and phenols
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Potassium fluoride incorporated on clinoptilolite nanoparticles (KF/CP NPs) by ion exchanging is found to be an effective and inexpensive heterogeneous nanocatalyst for chemoselective silylation of alcohols and phenols with 1,1,1,3,3,3-hexamethyldisilazane (HMDS) at room temperature. Nano-powder of clinoptilolite (CP) was prepared using a planetary ball mill mechanically method and characterized by dynamic light scattering (DLS), X-ray powder diffraction (XRD) and scanning electron microscope (SEM) analyses. Almost all of products were obtained in high yields as well as short reaction times and the catalyst was also reused eight times without loss of its catalytic activity.
- Oladee, Razieh,Zareyee, Daryoush,Khalilzadeh, Mohammad A.
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p. 731 - 737
(2021/03/31)
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- Synthesis and characterization of a bifunctional nanomagnetic solid acid catalyst (Fe3O4@CeO2/SO42?) and investigation of its efficiency in the protection process of alcohols and phenols via hexamethyldisilazane under solvent-free conditions
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In this research, Fe3O4@CeO2 (FC) was synthesized using the coprecipitation method and functionalized by an ammonium sulfate solution to achieve a heterogeneous solid acid Fe3O4@CeO2/SO42? (FCA) catalyst. The synthesized bifunctional catalyst was used in the protection process of alcohols and phenols using hexamethyldisilazane (HMDS) at ambient temperature under solvent-free conditions. Due to its excellent magnetic properties, FCA can easily be separated from the reaction mixture and reused several times without significant loss in its catalytic activity. Excellent yield and selectivity, simple separation, low cost, and high recyclability of the nanocatalyst are outstanding advantages of this procedure. The characterization was carried out using different techniques such as Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), X-ray diffraction (XRD), and vibrating sample magnetometry (VSM).
- Mohammadiyan, Esmaeel,Ghafuri, Hossein,Kakanejadifard, Ali
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p. 171 - 178
(2018/09/12)
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- A simple and efficient room temperature silylation of diverse functional groups with hexamethyldisilazane using CeO2 nanoparticles as solid catalysts
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In this study, a mild and efficient method is developed for the silylation of diverse functional groups using CeO2 nanoparticles (n-CeO2) as solid catalysts with hexamethyldisilazane (HMDS) as silylating agent at room temperature. Alcohols, phenols and acids are silylated to their respective silyl derivatives with faster reaction rate while amines and thiols required relatively longer reaction time. Moreover, the solid catalyst is easily be separated from the reaction mixture and recycled more than five times without any obvious decay in its activity. Powder X-ray diffraction (XRD), transmission electron microscope (TEM), UV–vis diffuse reflectance spectra (UV-DRS) and Raman analyses revealed identical structural integrity, particle size, absorption edge and valence state for the reused solid compared to the fresh solid catalyst.
- Anbu, Nagaraj,Vijayan, Chellappa,Dhakshinamoorthy, Amarajothi
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- Application of a novel nano-immobilization of ionic liquid on an MCM-41 system for trimethylsilylation of alcohols and phenols with hexamethyldisilazane
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3-[(3-(Trisilyloxy)propyl)chloride]-1-methylimidazolium tribromide ionic liquid supported on MCM-41 [nano-MCM-41@(CH2)3-1-methylimidazole]Br3 as a novel heterogeneous nano-catalyst was easily prepared and characterized usi
- Zolfigol, Mohammad Ali,Sajjadifar, Sami,Ghorbani-Choghamarani, Arash,Tami, Farzaneh
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p. 7093 - 7106
(2018/08/17)
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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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- Activation of hexamethyldisilazane (HMDS) by TiO2 nanoparticles for protection of alcohols and phenols: the effect of the catalyst phase on catalytic activity
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Anatase TiO2 nanoparticles (TiO2 NPs) were synthesized by the sol–gel method using titanium tetra-isopropoxide (TTIP), isopropyl alcohol, and distilled water and then calcined at 400?°C for 3?h. X-ray diffraction and scanning electron microscopy methods, and Fourier transform infrared spectroscopy were used for characterization of the obtained TiO2 NPs. The obtained anatase TiO2 NPs were used as heterogeneous catalyst for trimethylsilation of various alcohols or phenols with hexamethyldisilazane (HMDS) in CH3CN at room temperature. High to quantitative yields of the products were obtained within short reaction times at room temperature using a very low loading of pure TiO2 NPs without any post-modification with Bronsted or Lewis acid species such as ClSO3H or HClO4. The catalyst can be recycled at least three times without significant loss of its activity. The results of this study provide evidence that the pure anatase phase of TiO2 exhibits higher catalytic activity in terms of catalyst loading and required reaction time compared to a mixture of anatase and rutile phases found in the commercial samples for trimethylsilation of various alcohols or phenols with HMDS.
- Azad, Alireza,Dekamin, Mohammad G.,Afshar, Shahrara,Tadjarodi, Azadeh,Mollahosseini, Afsaneh
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p. 2951 - 2963
(2018/04/11)
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- Magnetic nanoparticle-supported DABCO tribromide: A versatile nanocatalyst for the synthesis of quinazolinones and benzimidazoles and protection/deprotection of hydroxyl groups
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1,4-Diazabicyclo[2.2.2]octane tribromide supported on magnetic Fe3O4 nanoparticles (MNPs-DABCO tribromide) as a novel heterogeneous tribromide type compound was found to be an efficient and reusable nanocatalyst for the one-pot synthesis of 2-arylquinazolin-4(3H)-ones and 2-aryl-1H-benzo[d]imidazoles through oxidative cyclization of aldehydes with 2-aminobenzamides and 1,2-phenylenediamine, respectively. Also, MNPs-DABCO tribromide catalyzed trimethylsilylation/tetrahydropyranylation and desilylation/depyranylation of a wide variety of alcohols and phenols through changing the solvent medium at room temperature.
- Rostami, Amin,Pourshiani, Omid,Navasi, Yahya,Darvishi, Neda,Saadati, Shaghayegh
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p. 9033 - 9040
(2017/08/29)
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- Nano Fe3O4@ZrO2/SO42?: A highly efficient catalyst for the protection and deprotection of hydroxyl groups using HMDS under solvent-free condition
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In this work, we introduce a new procedure for the protection and deprotection process of various types of alcohols and phenols by HMDS in the presence of nano magnetic sulfated zirconia (Fe3O4@ZrO2/SO42?) as a solid acid catalyst under very mild and solvent-free condition. This method has interesting advantages like short reaction times and a simple workup process. With regard to some outstanding benefits of this new heterogeneous catalyst such as excellent yield, reusability of the catalyst and easy thermal stability, high acidity, strong and excellent magnetic properties, this method can be very interesting in aspect of green chemistry Principles.
- Ghafuri, Hossein,Paravand, Fatemeh,Rashidizadeh, Afsaneh
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supporting information
p. 129 - 135
(2016/12/24)
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- Chlorozincate(II) acidic ionic liquid: Efficient and biodegradable silylation catalyst
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A practical and highly efficient silylation of alcohol and phenol derivatives with hexamethyldisilazane (HMDS) using acidic ionic liquids under mild reaction conditions is described. A series of Br?nsted as well as Br?nsted–Lewis acidic ionic liquids were prepared and their performance investigated for the silylation of a wide variety of alcohols and phenols with HMDS. Imidazole- as well as N-methyl-2-pyrrolidone-based acidic ionic liquids have a higher catalytic activity for the protection of sensitive, hindered alcohols and phenols, thus providing an environmentally begin and versatile alternative to current acid catalysts. In addition, the acidic ionic liquids are reusable, being recovered easily and reused several times without significant deterioration in catalytic activity.
- Abbasi, Faezeh,Azizi, Najmedin,Abdoli-Senejani, Masumeh
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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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- Tributyltin grafted onto the surface of 3-aminopropyl functionalized γ-Fe2O3 nanoparticles: A magnetically-recoverable catalyst for trimethylsilylation of alcohols and phenols
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Bonding of a homogenous tributyltin chloride catalyst on the surface of functionalized magnetic nanoparticles provides a new stable, efficient and magnetically recyclable catalyst for trimethylsilylation of alcohols and phenols with hexamethyldisilazan un
- Nikbakht, Fatemeh,Ghonchepour, Ehsan,Ziyadi, Hakimeh,Heydari, Akbar
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p. 34428 - 34434
(2014/10/15)
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- Rice husk ash: A new, cheap, efficient, and reusable reagent for the protection of alcohols, phenols, amines, and thiols
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Amild, efficient, and eco-friendly protocol for the protection of alcohols and phenols as trimethylsilyl ethers has been developed using rice husk ash as a reagent. This reagent is also able to catalyze the acetylation of alcohols, phenols, thiols, and amines with acetic anhydride. All reactions were performed under mild conditions in good to high yields. Copyright
- Shirini,Akbari-Dadamahaleh, Somayeh,Mohammad-Khah, Ali
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p. 577 - 586
(2014/06/09)
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- Rice husk: Introduction of a green, cheap and reusable catalyst for the protection of alcohols, phenols, amines and thiols
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A mild, efficient and eco-friendly protocol for the chemoselective protection of benzylic and primary and less hindered secondary aliphatic alcohols and phenols as trimethylsilyl ethers and different types of amines as N-tert-butylcarbamates is developed using rice husk (RiH) as the catalyst. This reagent is also able to catalyze the acetylation of alcohols, phenols, thiols and amines with acetic anhydride. Easy work-up, relatively short reaction times, excellent yields and low cost, availability and reusability of the catalyst are the striking features of this methodology, which can be considered to be one of the best and general methods for the protection of alcohols, phenols, thiols and amines. In addition, the use of a green reagent in the above-mentioned reactions results in a reduction of environmental pollution and of the cost of the applied methods.
- Shirini, Farhad,Akbari-Dadamahaleh, Somayeh,Mohammad-Khah, Ali,Aliakbar, Ali-Reza
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p. 164 - 170
(2014/03/21)
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- 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
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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.
- Abri, Abdolreza,Ranjdar, Somayeh
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p. 929 - 934
(2014/10/16)
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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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- Efficient room-temperature O-silylation of alcohols using a SBA-15-supported cobalt(II) nanocatalyst
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The O-silylation of OH groups of alcohols and phenols with hexamethyldisilazane (HMDS) was achieved in high-to-excellent yields using catalytic quantities of a SBA-15-supported cobalt(II) nanocatalyst (typically 0.5 mol-%) at room temperature and under solvent-free conditions. Furthermore, the heterogeneous catalyst showed an excellent durability and can be conveniently reused by filtration for at least twelve times without any noticeable loss of activity. Copyright
- Rajabi, Fatemeh,Luque, Rafael,Serrano-Ruiz, Juan Carlos
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p. 1823 - 1828
(2012/10/29)
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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
-
-
- Highly atom economical uncatalysed and I2-catalysed silylation of phenols, alcohols and carbohydrates, using HMDS under solvent-free reaction conditions (SFRC)
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An uncatalysed silylation of phenols, regardless on the aggregate state and nature of the substituents with 0.55 equiv of HMDS under solvent-free reaction conditions (SFRC) at room temperature is reported. Sterically hindered phenols, carbohydrates and most of the alcohols additionally required a catalytic amount (up to 2 mol %) of iodine. The reaction protocol is very simple; obtaining a pure product, particularly of uncatalysed reactions, was frequently a completely solvent-free process.
- Jereb, Marjan
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experimental part
p. 3861 - 3867
(2012/06/30)
-
- 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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- A mild and highly efficient method for the preparation of silyl ethers using Fe(HSO4)3/Et3N by chlorosilanes
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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.
- Abri, Abdolreza,Assadi, Mohammad Galeh,Pourreza, Samira
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p. 1449 - 1454
(2013/03/13)
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- Cross-coupling of aryl/alkenyl silyl ethers with grignard reagents through nickel-catalyzed CO bond activation
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CO activation and its application have drawn much attention since oxygen-based electrophiles are easily available, less toxic, and more environmentally benign. This letter presents systematically results on the Ni-catalyzed KumadaTamaoCorriu coupling based on siloxy arenes/alkenes, which provides a new strategy of silyl protection/CC bond formation sequence in organic synthesis.
- Zhao, Fei,Yu, Da-Gang,Zhu, Ru-Yi,Xi, Zhenfeng,Shi, Zhang-Jie
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p. 1001 - 1003
(2011/12/05)
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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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- 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 efficient trimethylsilyl protection of hydroxyl groups catalyzed by niobium(V) chloride
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An efficient and convenient procedure for the trimethylsilylation of a wide variety of alcohols, including primary, benzylic, secondary, and phenols with hexamethyldisilazane, has been developed. The reactions were carried out at room temperature in the presence of a catalytic amount of niobium(V) chloride and afforded the corresponding trimethylsilyl ethers in high to excellent yields in short time. Copyright Taylor & Francis Group, LLC.
- Hou, Jun-Tao,Chen, Hong-Li,Zhang, Zhan-Hui
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experimental part
p. 88 - 93
(2011/04/22)
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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)
-
- Tetrabutylammonium phthalimide-N-oxyl: An efficient organocatalyst for trimethylsilylation of alcohols and phenols with hexamethyldisilazane
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Tetrabutylammonium phthalimide-N-oxyl (TBAPINO) was found to be an effective organocatalyst for rapid, simple and chemoselective protection of the hydroxyl group of alcohols and phenols using hexamethyldisilazane (HMDS) under mild conditions. The low catalyst loading, high to quantitative yields and simple removal of the catalyst from the reaction mixture illustrate the other attractive features of this protocol.
- Dekamin,Yazdaninia,Mokhtari,Naimi-Jamal
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experimental part
p. 537 - 544
(2012/06/18)
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- Cross-linked poly(4-vinylpyridine/styrene) copolymer-supported bismuth(III) triflate: An efficient heterogeneous catalyst for silylation of alcohols and phenols with HMDS
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Cross-linked poly(4-vinylpyridine/styrene) copolymer-supported bismuth(III) triflate (30P/S-Bi) effectively activates hexamethyldisilazane (HMDS) for the silylation of alcohols and phenols. By the use of this heterogeneous catalytic system, a wide range of alcohols as well as phenols are converted into their corresponding trimethylsilyl ethers in high yield under mild reaction conditions. The catalyst was reused more than 10 times without significant loss of its catalytic activity.
- Lee, Sang-Hyeup,Kadam, Santosh T.
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experimental part
p. 608 - 615
(2011/11/12)
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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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- 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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- Magnesium hydrogensulfate [Mg(HSO4)2] as an efficient catalyst for the preparation of silyl ethers, dibenzo[a,j]xanthenes, and octahydroxanthene derivatives
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Magnesium hydrogensulfate [Mg(HSO4)2], as a heterogeneous solid acid catalyst, has been used for the mild formation of trimethylsilyl (TMS) ethers from various primary, secondary, and tertiary aliphatic alcohols; aromatic alcohols; a
- Shaterian, Hamid Reza,Doostmohammadi, Razieh,Khorami, Fahimeh,Ghashang, Majid
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experimental part
p. 171 - 180
(2010/04/05)
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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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- 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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- Silylation of alcohols and phenols using hexamethyldisilazane catalyzed by N,N'-diiodo-N,N'-1,2-ethanediyl bis(p-toluenesulfonamide) under solvent-free and microwave conditions
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N,N'-Diiodo-N,N'-1,2-ethanediyl bis(p-toluenesulfonamide) (NIBTS) is an effective catalyst for the silylation of alcohols and phenols using hexamethyldisilazane under solvent-free and microwave conditions. Supplemental materials are available for this art
- Ghorbani-Vaghei, Ramin,Malaekehpoor, Seyedeh Mina
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experimental part
p. 582 - 587
(2010/06/15)
-
- Nafion SAC-13: heterogeneous and reusable catalyst for the activation of HMDS for efficient and selective O-silylation reactions under solvent-free condition
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Nafion SAC-13 effectively activates hexamethyldisilazane (HMDS) for the efficient and selective silylation of alcohols. Primary, secondary, and tertiary alcohols and phenols are efficiently converted to their corresponding silylethers in short reaction ti
- Rajagopal, Gurusamy,Lee, Hanbin,Kim, Sung Soo
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experimental part
p. 4735 - 4741
(2009/10/09)
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- A Facile and efficient trimethylsilylation of hydroxyl groups using silica-supported zinc chloride and alumina-supported sodium hydrogensulfate as recyclable heterogeneous catalysts
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Silica-supported zinc chloride (SiO2-ZnCl2) and novel alumina-supported sodium hydrogensulfate (NaHSO4-Al 2O3) as recyclable heterogeneous catalysts have been used for the mild trimethylsilylation of hydroxyl groups under ambient conditions. This procedure also allows for the selective protection of primary and secondary alcohols in the presence of tertiary alcohols.
- Shaterian, Hamid Reza,Khorami, Fahimeh,Doostmohammadi, Razieh,Amirzadeh, Azita,Ghashang, Majid
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experimental part
p. 2227 - 2237
(2010/04/25)
-
- Novel and highly effective method for the trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS), catalyzed by I2 generated in situ using Fe(NO3)3 · 9 H 2O/NaI under heterogeneous and neutral conditions
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Structurally diverse alcohols and phenols were trimethylsilylated in a clean and efficient reaction with hexamethyldisilazane (HMDS) based on the use of I2 generated in situ from Fe(NO3)3 · 9 H2O/NaI. The reaction occurs very rapid in good-to-high yield in CH2Cl2 at room temperature, and the use of toxic and corrosive molecular I2 is avoided.
- Khazaei, Ardeshir,Rahmati, Sadegh,Rostami, Amin
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experimental part
p. 1434 - 1438
(2009/10/16)
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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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- 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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- Trimethylsilylation of alcohols and phenols, and direct acetylation of silyl ethers catalyzed by Fe(ClO4)3.6H2O
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In this article, a mild and efficient protocol for the trimethylsilylation of various aliphatic and benzylic alcohols and phenols with trimethylsilyl chloride using a catalytic amount of ferric perchlorate at room temperature and relatively short reaction times in good to excellent yields is reported. Direct acetylation of trimethylsilyl ethers catalyzed with Fe(ClO4)3.6H2O(0.02 mmol)/Fe(ClO4)3SiO2(0.2 g) using acetic anhydride at ambient temperature is also reported.
- Oskooie, Hossein A.,Heravi, Majid M.,Tehrani, Maryam H.,Behbahani, Farahnaz K.,Heravi, Omid M.
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experimental part
p. 1729 - 1737
(2010/01/17)
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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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- 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 method for the silylation of hydroxyl groups with hexamethyldisilazane (HMDS) catalyzed by aluminum tris(dihydrogen phosphate) under solvent-free and ambient conditions
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A highly efficient and mild procedure for the trimethylsilylation of a wide variety of alcohols, including primary, benzylic, secondary, hindered secondary, tertiary, phenols, and oximes with hexamethyldisilazane (HMDS), using Al(H2PO4)3 as a recyclable heterogeneous catalyst at room temperature in a few minutes with excellent yields under solvent-free conditions is described.
- Shaterian, Hamid Reza,Ghashang, Majid,Riki, Nassrin Tajbakhsh,Asadi, Manijeh
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p. 841 - 845
(2008/12/20)
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- Alumina sulfuric acid as an efficient and recyclable heterogeneous catalyst for the O-silylation of alcohols, phenols, and oximes
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Alumina sulfuric acid as a recyclable catalyst conducts the transformation of various types of alcohol, phenols, and oximes with hexamethyldisilazane (HMDS) to the corresponding O-trimethylsilylated compounds in good to excellent yields under mild and ambient conditions with short reaction times. The method is highly selective for the conversion of primary alcohols in the presence of secondary and tertiary alcohols. Additionally, the catalyst can be easily recovered and reused at least eight times without detectable loss of reactivity.
- Shaterian, Hamid Reza,Khorami, Fahimeh,Amirzadeh, Azita,Ghashang, Majid,Hosseinian, Asghar
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scheme or table
p. 2584 - 2595
(2009/08/15)
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- Silica-supported ferric chloride (silica-FeCl3): A reusable, easily controllable catalyst for the protection of hydroxyl groups under mild and ambient conditions
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Diverse alcohols, phenols, and naphthols were converted into their corresponding trimethylsilyl ether effectively with hexamethyldisilazane in the presence of silica-FeCl3 under solvent-free and ambient conditions with short reaction time in good to excellent yields. Work up procedure is easy, and the catalyst can be recovered by simple filtration and reused. Copyright Taylor & Francis Group, LLC.
- Shaterian, Hamid Reza,Ghashang, Majid,Hosseinian, Asghar
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experimental part
p. 2108 - 2118
(2009/07/18)
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- Alumina perchloric acid (Al2O3-HClO4) as an efficient heterogeneous catalyst for modified preparation of trimethylsilyl ethers
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A highly efficient and mild procedure for the trimethylsilylation of a wide variety of alcohols, including primary, benzylic, secondary, hindered secondary, tertiary, phenols, and oximes with hexamethyldisilazane (HMDS) using alumina perchloric acid (Al2O3-HClO4) as recyclable heterogeneous catalyst in excellent yields with short reaction times (3-65 min) under ambient conditions is described. Copyright Taylor & Francis Group, LLC.
- Shaterian, Hamid Reza,Khorami, Fahimeh,Amirzadeh, Azita,Ghashang, Majid
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experimental part
p. 2865 - 2874
(2009/09/25)
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- A highly efficient method for the silylation of alcohols, phenols, and naphthols using HMDS in the presence of zinc oxide (ZnO) as economical heterogeneous catalyst
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Variety alcohols, phenols, and naphthols were effectively converted into their corresponding trimethylsilyl ether with hexamethyldisilazane in the presence of zinc oxide under very mild and ambient conditions with short reaction time in good to excellent yields.
- Shaterian, Hamid Reza,Ghashang, Majid
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p. 194 - 204
(2008/12/21)
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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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