- Dodecatungstocobaltate heteropolyanion encapsulation into MIL-101(Cr) metal–organic framework scaffold provides a highly efficient heterogeneous catalyst for methanolysis of epoxides
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A heterogeneous catalyst was synthesized by encapsulation of a Keggin-type heteropolytungstate, potassium dodecatungstocobaltate trihydrate, K5[CoW12O40]·(Co-POM), into chromium(III) terephthalate (MIL-101). Encapsulation was achieved via a ‘build bottle around ship’ strategy in aqueous media, following a hydrothermal method. The structure of the resulting crystalline solid was characterized using X-ray diffraction, correlated with Fourier transform infrared and UV–visible spectroscopy. The metal content was analysed using optical emission spectroscopy. Transmission electron microscopy was used to measure particle size and N2 adsorption in a Brunauer–Emmett–Teller instrument to characterize the specific surface area. The catalytic activity was investigated using methanolysis of epoxides under mild conditions as a test reaction. The turnover frequency of the heterogeneous Co-POM@MIL-101 catalyst was more than 20 times higher than that of the homogeneous Co-POM catalyst. The Co-POM@MIL-101 catalyst was reused several times with negligible leaching of Co-POM and with no considerable loss of its initial efficiency. The simplicity of preparation, extraordinary stability and high reactivity make Co-POM@MIL-101 an exceptional catalytic matrix that is easily separable from reaction media.
- Marandi, Afsaneh,Tangestaninejad, Shahram,Moghadam, Majid,Mirkhani, Valiollah,Mechler, Adam,Mohammadpoor-Baltork, Iraj,Zadehahmadi, Farnaz
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- Ru(III) complex anchored onto amino-functionalized MIL-101(Cr) framework via post-synthetic modification: an efficient heterogeneous catalyst for ring opening of epoxides
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In this work, the metallo Schiff base-functionalized metal–organic framework was prepared by post-synthetic method and used as an electron-deficient catalyst for the alcoholysis of epoxides. In this manner, the aminated MIL-101 was modified with 2-pyridine carboxaldehyde and then the prepared Schiff base reacted with RuCl3. This new catalyst, MIL-101–NH2–PC–Ru, was characterized by Fourier transform infrared, UV–Vis spectroscopic techniques, X-ray diffraction, BET, inductively coupled plasma atomic emission spectroscopy and field-emission scanning electron microscopy. In the presence of this heterogeneous catalyst, ring opening of epoxides was performed under mild condition to show the significant ability and successful applications of Lewis acid containing catalysts in corporation with metal–organic frameworks. The reusability of the catalyst was also investigated. No noticeable decrease in the catalytic activity was found after four consecutive times.
- Jafari, Aneseh Khalatbari,Kardanpour, Reihaneh,Tangestaninejad, Shahram,Mirkhani, Valiollah,Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Zadehahmadi, Farnaz
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Read Online
- Zirconium triflate grafted on SBA-15 as a highly efficient solid acid catalyst for ring opening of epoxides by amines and alcohols
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Metal (Al, Ti, Zr) triflate grafted mesoporous SBA-15 (AlTf/S, TiTf/S, ZrTf/S) samples were synthesized as inexpensive solid acid materials by a simple one-pot-two-step synthesis methodology. These materials were characterized by X-ray diffraction, N2-sorption, thermogravimetric analysis, Fourier transform infrared spectroscopy (FT-IR), in-situ pyridine FT-IR spectroscopy, and elemental analysis. ZrTf/S was found to be a highly efficient and reusable solid acid catalyst for ring opening of epoxides with amines and alcohols and produced β-amino alcohols and β-alkoxy alcohols respectively under ambient reaction conditions. The ZrTf/S catalyst showed the highest activity, which was attributed to its high acidity compared with that of the Ti and Al containing samples.
- Tayade, Kamlesh N.,Wang, Lianyue,Shang, Sensen,Dai, Wen,Mishra, Manish,Gao, Shuang
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p. 758 - 766
(2017/04/24)
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- An Fe3O4 nanoparticle-supported Mn (II)-azo Schiff complex acts as a heterogeneous catalyst in alcoholysis of epoxides
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In this paper, an azo-containing Schiff base complex of manganese [Mn2+-azo ligand@APTES-SiO2@Fe3O4] immobilized on chemically modified Fe3O4 nanoparticles has been used as a magnetically retrievable catalyst for the alcoholysis of different epoxides to their corresponding alkoxy alcohols with methanol, ethanol and n-propanol. The newly magnetic nanoparticles (MNPs) were characterized by Fourier transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive X-ray analysis (EDX) and vibrating sample magnetometry (VSM).
- Olia, Fahimeh Karami,Sayyahi, Soheil,Taheri, Narges
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p. 370 - 376
(2017/03/15)
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- Aniline-terephthalaldehyde resin p-toluenesulfonate (ATRT) as a highly efficient and reusable catalyst for alcoholysis, hydrolysis, and acetolysis of epoxides
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Alcoholysis, hydrolysis, and acetolysis of epoxides were carried out in the presence of a catalytic amount of aniline-terephthalaldehyde resin p-toluenesulfonate (ATRT) to give the corresponding β-substituted alcohols in good yields. Alcoholysis and hydrolysis of epoxides catalyzed by ATRT proceeded faster than those by pyridinium p-toluenesulfonate (PPTS).
- Tanemura, Kiyoshi,Suzuki, Tsuneo
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supporting information
p. 1781 - 1789
(2016/11/17)
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- A highly efficient protocol for regioselective ring-opening of epoxides with alcohols, water, acetic acid, and acetic anhydride catalyzed by SbF3
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SbF3as an efficient catalyst has been used for regioselective alcoholysis, acetolysis and hydrolysis of epoxides to the corresponding β-alkoxy, β-acetoxy alcohols, and 1,2-diols in high to excellent yields. This study also represents a convenient synthesis of vic-diacetates from ring-opening of epoxides with acetic anhydride.
- Zeynizadeh, Behzad,Gilanizadeh, Masumeh,Aminzadeh, Farkhondeh Mohammad
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p. 1051 - 1056
(2016/07/06)
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- Graphite oxide: A simple and efficient solid acid catalyst for the ring-opening of epoxides by alcohols
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A simple, efficient, and general procedure for the ring-opening of epoxides with various alcohols to give the corresponding β-alkoxy alcohols using graphite oxide (GO) as the catalyst, under very mild reaction conditions is described. The method proceeds in good to excellent yields and in short reaction times at room temperature under metal-free conditions.
- Mirza-Aghayan, Maryam,Alizadeh, Mahdi,Molaee Tavana, Mahdieh,Boukherroub, Rabah
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p. 6694 - 6697
(2014/12/11)
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- Erbium(III) triflate is a highly efficient catalyst for the synthesis of β-alkoxy alcohols, 1,2-diols and β-hydroxy sulfides by ring opening of epoxides
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Chemo- and stereoselectivity in the ring-opening reaction of epoxides with erbium(III) triflate are described. Epoxides can be cleaved under neutral conditions with alcohols and thiols in the presence of catalytic amounts of Lewis acid, affording the corresponding β-alkoxy alcohols and β-hydroxy sulfides in high yields. In water, epoxide ring opening occurs to produce the corresponding diols in good yields.
- Dalpozzo, Renato,Nardi, Monica,Oliverio, Manuela,Paonessa, Rosina,Procopio, Antonio
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experimental part
p. 3433 - 3438
(2010/02/28)
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- Ring-opening reactions of epoxides catalyzed by molybdenum(VI) dichloride dioxide
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Transformation of epoxides to β-alkoxy alcohols, acetonides, and α-alkoxy ketones is achieved by using molybdenum(VI) dichloride dioxide (MoO2Cl2) as a catalyst. Alcohol, aldehyde, oxime, tosyl, and tert-butyldimethylsilyl functional groups are tolerated during the methanolysis and acetonidation of the functionalized epoxides. No polymerization product is observed with any of the epoxides. Direct conversion of epoxides devoid of sensitive functional groups into the corresponding α-methoxy ketone is achieved in a single step by using the MoO2Cl 2/Oxone system. Georg Thieme Verlag Stuttgart.
- Jeyakumar, Kandasamy,Chand, Dillip Kumar
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p. 807 - 819
(2008/09/21)
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- Mild and efficient ring opening of epoxides catalyzed by potassium dodecatungstocobaltate(III)
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Efficient ring opening of epoxides under mild conditions is reported. Potassium dodecatungstocobaltate(III) trihydrate was used as an efficient catalyst for the alcoholysis and acetolysis of epoxides. Conversion of epoxides to thiiranes was also performed efficiently in the presence of this catalyst. Springer-Verlag 2005.
- Tangestaninejad, Shahram,Moghadam, Majid,Mirkhani, Valiollah,Yadollahi, Bahram,Mirmohammadi, S. Mohammad R.
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p. 235 - 242
(2007/10/03)
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- MONOMER, POLYMER, AND OCULAR LENS AND CONTACT LENS EACH OBTAINED THEREFROM
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A monomer as represented by general formula (a) or (a') below, with which a polymer having high oxygen permeability and transparency and suited to an ophthalmic lens is obtained, is provided. Suitable monomers have the formula: wherein A is a siloxanyl group; R1 and R2 are H or methyl groups; R3 is a substituted group that is selected from the group consisting of alkyl groups with 1 to 20 carbon atoms that may be substituted and aryl groups with 6 to 20 carbon atoms that may be substituted; m indicates an integer of 0 to 200.
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- Rapid and efficient ring opening of epoxides catalyzed by a new electron deficient tin(IV) porphyrin
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The new electron deficient tin(IV) tetraphenylporphyrinato trifluoromethanesulfonate, [SnIV(tpp)(OTf)2], was used as an efficient catalyst for the alcoholysis, hydrolysis and acetolysis of epoxides. Conversion of epoxides to thiiranes and acetonides were also performed efficiently in the presence of this catalyst.
- Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Shaibani, Reza
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p. 6105 - 6111
(2007/10/03)
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- Silica sulfuric acid; an efficient and reusable catalyst for regioselective ring opening of epoxides by alcohols and water
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The nucleophilic ring opening reactions of epoxides by aliphatic alcohols and water are achieved efficiently in the presence of catalytic amounts of silica sulfuric acid with high degree of regioselectivity. The catalyst is reusable and can be applied several times without any decrease in the yield of reactions.
- Salehi, Peyman,Dabiri, Minoo,Zolfigol, Mohammad Ali,Fard, Mohammad Ali Bodaghi
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p. 1113 - 1121
(2007/10/03)
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- Efficient regio- and stereoselective ring opening of epoxides with alcohols, acetic acid and water catalyzed by ammonium decatungstocerate(IV)
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Epoxides can be cleaved in a regio- and stereoselective manner under neutral conditions with alcohols and acetic acid in the presence of catalytic amounts of decatungstocerate(IV) ion, ([CeW10O36] 8-), affording the corresponding β-alkoxy and β-acetoxy alcohols in high yields. In water, ring opening of epoxides occurs with this catalyst to produce the corresponding diols in good yields.
- Mirkhani, Valiollah,Tangestaninejad, Shahram,Yadollahi, Bahram,Alipanah, Ladan
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p. 8213 - 8218
(2007/10/03)
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- Supported ATRP and giant polymers
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Surface-initiated Atom Transfer Radical Polymerization (ATRP) produces surface-bound films with thicknesses up to tens of microns. We report on the possible existence of micron-sized, individual polymer chains in these films.
- Von Natzmer, Peter,Bontempo, Debora,Tirelli, Nicola
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p. 1600 - 1601
(2007/10/03)
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- Magnesium hydrogensulfate: A cheap and efficient catalyst for the conversion of epoxides into β-alkoxy alcohols, vicinal-diols, and thiiranes
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The nucleophilic ring opening reactions of epoxides by aliphatic alcohols and water are achieved efficiently in the presence of catalytic amounts of magnesium hydrogensulfate, Mg(HSO4)2, with high degree of regioselectivity. The reactions are chemoselective and many of the other functional groups such as ethereal carbon oxygen bonds as well as carbon-carbon double bond remain intact under the reaction conditions. Epoxides also react with thiourea or ammonium thiocyanate in the presence of Mg(HSO 4)2 to afford the corresponding thiiranes in good to excellent yields.
- Salehi, Peyman,Khodaei, Mohammad Mahdi,Zolfigol, Mohammad Ali,Keyvan, Afsaneh
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p. 3041 - 3048
(2007/10/03)
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- Bismuth(III) chloride (BiCl3); an efficient catalyst for mild, regio- and stereoselective cleavage of epoxides with alcohols, acetic acid and water
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Epoxides can be cleaved in a regio- and stereoselective manner with alcohols, acetic acid and water in the presence of catalytic amounts of bismuth(III) chloride, affording the corresponding β-alkoxy and β-acetoxy alcohols and diols in high yields.
- Mohammadpoor-Baltork,Tangestaninejad,Aliyan,Mirkhani
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p. 2365 - 2374
(2007/10/03)
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- Iron(III) trifluoroacetate as an efficient catalyst for solvolytic and nonsolvolytic nucleophilic ring opening of epoxides
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Iron(III) trifluoroacetate was used as an efficient and nonhygroscopic catalyst for the alcoholysis, hydrolysis, and acetolysis of epoxides. The addition of chloride, bromide, iodide, and nitrate ions to epoxides to produce the corresponding 2-halo and 2-nitratoalkanols and also the conversion of epoxides to acetonides and thiiranes were also performed efficiently in the presence of this catalyst.
- Iranpoor, Nasser,Adibi, Hadi
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p. 675 - 680
(2007/10/03)
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- TiCl3(OTf) and TiO(TFA)2 efficient catalysts for ring opening of epoxides with alcohols, acetic acid and water
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TiCl3 (OTf) and TiO(TFA)2 can efficiently catalyze nucleophilic ring opening of epoxides in primary, secondary and tertiary alcohols, acetic acid and water to give the corresponding β-alkoxy alcohols, β-acetoxy alcohols and vicinal diols with high stereo- and regioselectivity in excellent yields. The reaction of optically active styrene oxide in MeOH with two titanium reagents was found to be highly stereospecific and afforded the corresponding S-(+)-2-methoxy-2-phenyl ethanol in 89-95% ee.
- Iranpoor, Nasser,Zeynizadeh, Behzad
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p. 1017 - 1024
(2007/10/03)
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- Highly efficient, regio- and stereoselective ring opening of epoxides and thiiranes with Ce(OTf)4
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Ceric triflate, Ce(OTf)4 is used as an efficient catalyst for ring opening of epoxides in the presence of alcohols, water, and acetic acid. The reactions proceed with high regio and stereoselectivity and in excellent yields. The reaction of R(+) styrene oxide with methanol occurs with excellent optical purity. Ring opening of thiiranes in alcohols, water and acetic acid followed by dimerisation to the corresponding disulfides occur efficiently in the presence of this reagent. A mild method for the preparation of dithianes from thiiranes and Ce(OTf)4 is also described.
- Iranpoor,Shekarriz,Shiriny
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p. 347 - 366
(2007/10/03)
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- Iodine and iodine supported on polyvinylpyrrolidone as catalysts and reagents for alcoholysis, hydrolysis, and acetolysis of epoxides and thiiranes
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Iodine and iodine supported on polyvinylpyrrolidone (betadine) have been used as catalysts for ring opening of epoxides and as reagent for ring-opening dimerization of thiiranes in alcohols, water, and acetic acid. The reactions occur with high regio-, chemo-, and stereoselectivity. The reaction of R-(+)-styrene oxide with I2 supported on PVP in methanol was found to be very stereospecific and the product was isolated in 93% ee.
- Iranpoor, Nasser,Tamami, Bahman,Niknam, Khodabakhsh
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p. 1913 - 1919
(2007/10/03)
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- Electrogenerated Acid as an Efficient Catalyst for Alcoholyses and Hydrolyses of Epoxides
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The electrochemical transformation of different epoxides to their corresponding β-alkoxy alcohols and diols was achieved by using an electrogenerated acid-catalyst.A competitive ring-opening reaction of activated epoxides in the presence of deactivated epoxides was also successfully carried out in both alcohols and water.
- Safavi, Afsaneh,Iranpoor, Nasser,Fotuhi, Lida
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p. 2591 - 2594
(2007/10/03)
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- Highly efficient, regio- and stereoselective alcoholysis of epoxides catalyzed with iron(III) chloride
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An efficient, catalytic, simple and mild method for the conversion of epoxides into their corresponding β-alkoxy alcohols was performed in primary, secondary and tertiary alcohols and in the presence of catalytic amounts of ferric chloride. The β-alkoxy alcohols were obtained with high stereo- and regioselectivity and in good to excellent yields.
- Iranpoor,Salehi
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p. 1152 - 1154
(2007/10/02)
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- Tris[Trinitrato Ce(IV)]paraperiodate, an efficient heterogeneous catalyst for alcoholysis, acetolysis and hydrolysis of epoxides
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Tristrinitrato [Ce(IV)]paraperiodate (TTCPP) catalyses ring opening of epoxides in alcohols and water stereo- and regioselectively and under heterogeneous conditions to produce the corresponding β-alkoxy alcohols and 1,2 diols respectively in good to high yields. In acetic acid, ring opening and dimerization of epoxides occurs with this catalyst to produce the corresponding succinic acid derivatives in high yields.
- Iranpoor,Zardaloo
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p. 1959 - 1969
(2007/10/02)
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- 2,3-Dichloro-5,6-dicyano-p-benzoquinone, an efficient, mild, neutral and highly regioselective catalyst for alcoholysis of epoxides
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Ring-opening reactions of epoxides with catalytic amounts of 2,3- Dichloro-5,6-Dicyano-p-Benzoquinone (DDQ) are performed with high regioselectivity under neutral conditions, in primary, secondary and tertiary alcohols as solvents and nucleophiles. The corresponding β- alkoxy alcohols were obtained in excellent yields.
- Iranpoor,Mohammadpour Baltork
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p. 735 - 738
(2007/10/02)
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- Mild, Efficient and Selective Opening of Epoxides with Alcohols Catalyzed by Ceric(IV) Ammonium Nitrate
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Commercially available Ceric(IV) Ammonium Nitrate (CAN) catalyzes nucleophilic ring opening of epoxides in primary, secondary and tertiary alcohols under mild conditions.The corresponding β-alkoxy-alcohols were obtained with high regio and stereoselectivity in high yields.
- Iranpoor, N.,Baltork, I. Mohammadpour
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p. 2789 - 2797
(2007/10/02)
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- Organosilicon compounds
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Silane or siloxane/polyether compositions obtained by reaction of a terminally unsaturated mono-epoxide with an alcohol, followed by hydrosilation.
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