- Mild, Effective and Selective Method for the Silylation of Alcohols Using Silazanes Promoted by Catalytic Tetrabutylammonium Fluoride
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The presence of catalytic amounts (ca. 0.02 equiv.) of tetrabutylammonium fluoride (TBAF) significantly promoted the silylation of alcohols using a variety of available silazanes under mild conditions with high chemoselectivity, wherein the choice of sila
- Tanabe, Yoo,Murakami, Masanari,Kitaichi, Kazuto,Yoshida, Yoshihiro
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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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- Room temperature silylation of alcohols catalyzed by metal organic frameworks
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The commercial Al(OH)(BDC) (BDC: 1,4-benzenedicarboxylic acid) metal organic framework (Basolite A100) is a suitable heterogeneous catalyst for the silylation of benzylic and aliphatic alcohols by hexamethyldisilazane in toluene at room temperature. Al(OH
- Dhakshinamoorthy, Amarajothi,Santiago-Portillo, Andrea,Concepción, Patricia,Herance, José R.,Navalón, Sergio,Alvaro, Mercedes,Garcia, Hermenegildo
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p. 2445 - 2449
(2017/07/24)
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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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- 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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- 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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- 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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- 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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- [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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- 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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- 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)
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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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- 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 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 mild, simple, efficient, and selective protection of hydroxyl groups using silica-supported sodium hydrogen sulfate as a heterogeneous catalyst
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A mild, simple, novel, and highly efficient method for the rapid protection of various primary, secondary, tertiary aliphatic alcohols, aromatic alcohols, and oximes using hexamethyldisilazane (HMDS) in the presence of silica-supported sodium hydrogen sulfate (NaHSO4-SiO2), as an active, inexpensive, nontoxic, heterogeneous, and readily available catalyst under ambient conditions is described. Timethylsilyl ethers were prepared in high to excellent yields, with short reaction times under mild and almost neutral reaction conditions at room temperature. Copyright Taylor & Francis Group, LLC.
- Shaterian, Hamid Reza,Doostmohammadi, Razieh,Ghashang, Majid,Rahmani, Mashaallah
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experimental part
p. 3127 - 3135
(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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- 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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- Iron(III) trifluoroacetate [Fe(F3CCO2)3] as an easily available, non-hygroscopic, non-corrosive, highly stable and a reusable Lewis Acid catalyst: Efficient O-silylation of α-hydroxyphosphonates, alcohols and phenols by he
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O-Silylation of hydroxyl groups of α-hydroxyphosphonates, primary, secondary tertiary-alcohols and phenols with HMDS was achieved in high to excellent yields using iron(III) trifluoroacetate [Fe(F3CCO2)3] as an easily avai
- Firouzabadi, Habib,Iranpoor, Nasser,Jafari, Abbas Ali,Jafari, Mohammad Reza
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p. 2711 - 2714
(2008/12/20)
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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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- 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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- 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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- Fluorination with ionic liquid EMIMF(HF)2.3 as mild HF source
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Hydrogen fluoride is a basic fluorinating reagent, but handling it is difficult. For this reason, some modified fluorinating reagents such as HF-pyridine, Et3N-HF, and poly(hydrogen fluoride) complex have been developed. Those reagents, however, still require aqueous work-up procedures which generate hydrogen fluoride. Recently, ionic liquids have received much attention because of the ease in handling them and the possibility of non-aqueous work-up. An ionic liquid, 3-ethyl-1-methyimidazolium oligo hydrogen fluoride (EMIMF(HF)2.3), which is stable in air and moisture, can be used as a hydrogen fluoride equivalent for some fluorination reactions; it does not require an aqueous work-up.
- Yoshino, Hideaki,Matsumoto, Kazuhiko,Hagiwara, Rika,Ito, Yasuhiko,Oshima, Koichiro,Matsubara, Seijiro
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- Efficient and practical protocol for silylation of hydroxyl groups using reusable lithium perchlorate dispread in silica gel under neutral condition
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A very efficient and mild procedure for the trimethylsilylation of a wide variety of alcohols, including primary, allylic, benzylic, secondary, hindered secondary, tertiary, and phenols with hexamethyldisilazane on the surface of silica gel dispersed with LiClO4 in room temperature at few minutes in excellent yields under neutral conditions is reported. This procedure also allows the excellent selectivity under LP-SiO2 system for silylation of alcohols in the presence of amine and phenolic hydroxy groups.
- Azizi, Najmedin,Yousefi, Rozbeh,Saidi, Mohammad R.
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p. 817 - 820
(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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- Anilinosilanes/TBAF catalyst: Mild and powerful agent for the silylation of sterically hindered alcohols
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We developed an efficient method for the silylation of alcohols using anilinosilane with tetrabutylammonium fluoride (TBAF) catalyst, wherein TMS, TES and TBS groups were smoothly introduced into silylation-resistant hindered alcohols under mild condition
- Iida, Akira,Horii, Atsushi,Misaki, Tomonori,Tanabe, Yoo
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p. 2677 - 2682
(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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- 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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- Hexamethyldisilazane in the presence of n,n′,n″n?- tetramethyltetra-2,3-pyridinoporphyrazinato copper (II) is a new, mild and highly efficient reagent for silylation of alcohols and phenols
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Alcohols and phenols are protected with hexamethyldisilazane in the presence of N,N′,N″,N?-tetramethyletra-2,3- pyridinoporphyrazinato copper (II) in good-to-excellent yields at room temperature.
- Akhlaghinia, Batool,Asadi, Mozafar,Safaee, Elham,Heydarpoor, Mozhgan
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p. 2099 - 2104
(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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- Reaction of carbonyl compounds with trialkylsilyl phenylselenide and tributylstannyl hydride under radical conditions
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A novel method for the hydrosilylation of carbonyl compounds has been developed. When carbonyl compounds were allowed to react with trimethylsilyl phenylselenide and tributylstannyl hydride in the presence of a catalytic amount of AIBN as the radical initiator, hydrosilylation of the carbonyl compounds efficiently proceeded to give the corresponding silyl ethers in moderate to good yields. In the absence of carbonyl compounds, the triethylsilyl hydride was obtained by the reaction of PhSeSiEt3 with Bu3SnH. Although the tributylgermyl phenylselenide instead of PhSeSiMe3 was treated with tributylstannyl hydride in the presence of a benzaldehyde under radical conditions, hydrogermylated product was not obtained and tributylgermyl hydride was mainly formed.
- Nishiyama, Yutaka,Kajimoto, Hiroyuki,Kotani, Kazuya,Nishida, Takuma,Sonoda, Noboru
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p. 5696 - 5700
(2007/10/03)
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- Tungstophosphoric acid (H3PW12O40) as a heterogeneous inorganic catalyst. Activation of hexamethyldisilazane (HMDS) by tungstophosphoric acid for efficient and selective solvent-free O-silylation reactions
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The role of tungstophosphoric acid (H3PW12O40) as heterogeneous organic catalysts was discussed. Activation of hexamethyldisilazane by tungstophosphoric acid for efficient and selective solvent-free O-silylation reactions
- Firouzabadi, Habib,Iranpoor, Nasser,Amani, Kamal,Nowrouzi, Farhad
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p. 2601 - 2604
(2007/10/03)
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- Hydrosilylation of carbonyl compounds using a PhSeSiMe3/Bu3SnH/AIBN system
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(equation presented) When carbonyl compounds were allowed to react with phenyl trimethylsilyl selenide and tributylstannyl hydride in the presence of a catalytic amount of AIBN as a radical initiator, the hydrosilylation of the carbonyl compounds efficiently proceeded to give the corresponding silyl ethers in moderate to good yields.
- Nishiyama, Yutaka,Kajimoto, Hiroyuki,Kotani, Kazuya,Sonoda, Noboru
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p. 3087 - 3089
(2007/10/03)
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- Facile O-silylation of tertiary alcohols in the presence of Mg-metal
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Treatment of aliphatic alcohols with trimethylsilyl chloride (TMSCl) in N,N-dimethylformamide (DMF) containing Mg-turning at room temperature brought about facile and efficient O-silylation to give the corresponding trimethylsilyl ethers in good to excellent yields. This method can be also available for sterically hindered tert-alcohols and alcohols having a variety of substituents which may be labile under the basic conditions used in the conventional O-silylation.
- Nishiguchi, Ikuzo,Kita, Yoshio,Watanabe, Masamitsu,Ishino, Yoshio,Ohno, Toshinobu,Maekawa, Hirofumi
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p. 1025 - 1027
(2007/10/03)
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- Nitrogen ligand complexes of metal chlorides as effective catalysts for the highly regio- and chemoselective silylation of hydroxyl groups with hexamethyldisilazane (HMDS) at room temperature
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Zn(bipy)3Cl2, Fe(bipy)Cl3, and Fe(tpp)Cl are effective catalysts for silylation of hydroxy groups with HMDS at room temperature in dry CH3CN. High selectivity is observed between primary and secondary hydroxy fu
- Firouzabadi,Sardarian,Khayat,Karimi,Tangestaninejad
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p. 2709 - 2719
(2007/10/03)
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- Clean nitrations: Novel syntheses of nitramines and nitrate esters by nitrodesilylation reactions using dinitrogen pentoxide (N2O5)
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In this novel nitration method dinitrogen pentoxide (N2O5) in an inert solvent is used as the nitrating agent, thereby removing the need for strong acids as the reaction medium. The N2O5 cleaves heteroatom-silicon bonds, in silylamines and silyl ethers respectively, to yield the desired energetic groupings (nitramines or nitrate esters respectively) without liberation of acids which would occur with conventional substrates (amines or alcohols). These nitrodesilylation reactions proceed cleanly and in good yield, and the scope of the reaction is illustrated by 29 examples, some of which produce high energy compounds, notably plasticisers and an energetic polymer precursor. These reactions are therefore potentially clean nitrations for the manufacture of energetic compounds which will minimise the impact of this activity on the environment in the future.
- Millar, Ross W.,Philbin, Simon P.
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p. 4371 - 4386
(2007/10/03)
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- A Practical Method for Activation of Commercial Lithium Hydride: Reductive Silylation of Carbonyl Compounds with Lithium Hydride and Chlorotrimethylsilane
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Commercially available lithium hydride, an essentially inert metal hydride, can be activated as a hydride source by an equimolar amount of chlorotrimethylsilane and a catalytic amount of a Zn salt or Zn powder.Aromatic and aliphatic ketones, as well as no
- Ohkuma, Takeshi,Hashiguchi, Shohei,Noyori, Ryoji
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p. 217 - 221
(2007/10/02)
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- PROTECTION OF ALCOHOLS AND ACIDS WITH ALLYLSILANES CATALYZED BY IODINE OR IODOTRIMETHYLSILANE IN CHLORINATED HYDROCARBON
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Many triorganosilyl ethers and esters were prepared by the reaction of allylsilanes with alcohols catalyzed by iodine or iodotrimethylsilane in excellent yields.Bromine and bromotrimethylsilane were also effective catalysts.
- Hosomi, Akira,Sakurai, Hideki
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- USE OF ALLYLSILANES AS A NEW TYPE OF SILYLATING AGENT FOR ALCOHOLS AND CARBOXYLIC ACIDS
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A new convenient route to silyl ethers and esters from alcohols and carboxylic acids using allylsilanes in the presence of an acid catalyst in acetonitrile was developed.The present method is also applicable to t-butyldimethylsilylation.
- Morita, Tsuyoshi,Okamoto, Yoshiki,Sakurai, Hiroshi
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p. 835 - 838
(2007/10/02)
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