Zirconyl triflate, [ZrO(OTf)2], as a new and highly efficient catalyst for ring-opening of epoxides

Mohammadpoor‐Baltork, Iraj; Tangestaninejad, Shahram; Mirkhani, Valiollah; Shariati, Leyla; Babaghanbari, M.; Zarea, M.

doi:10.1007/bf03246171

Cited by 14 publications

(6 citation statements)

References 42 publications

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“…Although conditions are not necessarily consistent across studies, the observations are often similar. For terminal aliphatic epoxides, NaOH or the industrial “double metal cyanide” catalysts often give P1/P2 <0.1:1, , while many metal salts ,− give results similar to those with mineral acids such as H 2 SO 4 , with typical P1/P2 ratios of ∼0.8:1 . Some solid oxide catalysts have been reported to have selectivities up to 1.4:1 .…”

Section: Introductionmentioning

confidence: 99%

Enhancing the Regioselectivity of B(C₆F₅)₃-Catalyzed Epoxide Alcoholysis Reactions Using Hydrogen-Bond Acceptors

et al. 2019

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Epoxide alcoholysis is extensively employed in the synthesis of polymers and chemical intermediates, and it generally requires an acid catalyst for high rates and selectivity. Tris(pentafluorophenyl)borane [B(C6F5)3] is among few catalysts that are selective to primary alcohol products of terminal aliphatic epoxides that do not possess any directing groups. We have previously observed that under many conditions, the reaction regioselectivity increases with conversion. Here, we confirm a prediction from our earlier computational model, and we experimentally demonstrate that this increase is due to a selectivity-enhancing role of the reaction products. We then show that deliberate addition of catalytic amounts of certain diols increases the reaction regioselectivity. Cis-1,2 or 1,3-diols are required to enhance selectivity, consistent with a mechanism where extended hydrogen-bonding networks preferentially organize the reactants. This work presents a route to tune regioselectivity without altering the catalyst backbone and provides another example of the role of H-bonding networks in reactions taking place in protic media.

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Section: Introductionmentioning

confidence: 99%

Enhancing the Regioselectivity of B(C₆F₅)₃-Catalyzed Epoxide Alcoholysis Reactions Using Hydrogen-Bond Acceptors

et al. 2019

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“…This synthesis is thus limited by the commercial availability of the starting glycidyl ether. Two different approaches have been envisaged for the ring-opening reaction (Scheme ): alkoxide opening reaction that involves a previous reaction of the alcohol with metallic sodium and acid-catalyzed ring-opening reaction using several Lewis acids such as FeCl 3 , (ZrO(OTf) 2 ), I 2 /poly(4-vinylpyridinium), V IV (tpp)(OTf) 2 , or Sn IV (tpp)(OTf) 2 …”

Section: Introductionmentioning

confidence: 99%

Readily Scalable Methodology for the Synthesis of Nonsymmetric Glyceryl Diethers by a Tandem Acid-/Base-Catalyzed Process

Leal‐Duaso

Gracia-Barberán

Mayoral

et al. 2019

Org. Process Res. Dev.

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A useful optimized synthetic methodology has been designed for the obtaining of non-symmetric glyceryl diethers from epichlorohydrin. A tandem process combining a cheap, heterogeneous and fully recoverable acid catalyst and alkaline hydroxide is used for the synthesis of a variety of glycerol-derived ethers bearing different alkyl substituents in 1 and 3 positions.Different heterogeneous acid catalysts have been tested for the reaction of epichlorohydrin with several alcohols, the best results being obtained with readily available recoverable and inexpensive

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“…Due to simplicity and higher yields of one-pot procedures, more attention is focused on the synthesis of vicdiacetates in one step and in the presence of various catalyst. There are different reports on conversion of epoxides to vicdiacetates in the presence of various types of catalysts naming erbium (III) triflate, 3 4 Å molecular sieves, 4 ammonium-12molybdophosphate, 5 zirconyl triflate, 6 phosphomolybdic acid with and without silica gel support, 7 LiClO 4 , 8 Bu 3 P, 9 zeolite 10 and NaBH 4 , LiAlH 4 , CaH 2 hydride transfer agent. 11 To the best of our knowledge there is no report on epoxide conversion to vic-diacetates involving TiO 2 (anatase) nanoparticles (NPs), while it has been applied as catalyst for conversion of epoxides to β-amino alcohols 12 and also in various reactions including sulphur oxidation, 13 Hantzsch esters synthesis, 14 oxindole derivatives synthesis, 15 hydrogen production, 16 carboxymethylation and methylation of bisphenol A 17 and also dye degradation by polymer, and metal ion modified titanium dioxide.…”

Section: Introductionmentioning

confidence: 99%

TiO2 (Anatase) Nanoparticles a Novel Catalyst for Synthesis of vic-Diacetates as Biologically Active Compounds

Momen

Piri

Karimian

et al. 2018

jabr

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Introduction: This study represents efficient ring opening of epoxides to the corresponding vicinal diacetates in the presence of acetic anhydride. Different catalyst including molecular sieves, zirconyl triflate, LiClO 4 , zeolite, LiAlH 4 and some other catalyst were reported so far as efficient catalyst for epoxide ring opening and subsequent diacetylation. In the present study, catalytic amount of commercially available TiO 2 (anatase) nanoparticles (NPs) were used to promote reactions. Materials and Methods: According to X-ray diffraction (XRD) patterns, anatase is the main phase of the TiO 2 and scanning electron microscope (SEM)images revealed almost all the particles are under 100 nm in size. Existence of just oxygen and titanium peaks in EDS spectrum confirms high purity of catalyst. Results: It was found that catalyst revealed good reusability and could be used in 3 cycles without marked loss of efficiency for synthesis of vicdiacetates from epoxides. Reactions of structurally diverse epoxides in the presence of acetic anhydride and catalytic amount of titanium dioxide were set at 100°C, progress of the reactions were monitored by thin layer chromatography (TLC) and gas chromatography (GC) which resulted in good to excellent yields. Conclusions: In brief, the current work represents an efficient procedure for one-pot conversion of structurally different epoxides to the corresponding vic-diacetates. Comparison of cyclohexene oxide acetylation in the presence of titanium dioxide NPs and other catalyst confirmed acceptable efficiency of anatase titanium dioxide as a clean, safe and low cost catalyst for reaction promotion.

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Zirconyl triflate, [ZrO(OTf)2], as a new and highly efficient catalyst for ring-opening of epoxides

Cited by 14 publications

References 42 publications

Enhancing the Regioselectivity of B(C₆F₅)₃-Catalyzed Epoxide Alcoholysis Reactions Using Hydrogen-Bond Acceptors

Enhancing the Regioselectivity of B(C₆F₅)₃-Catalyzed Epoxide Alcoholysis Reactions Using Hydrogen-Bond Acceptors

Readily Scalable Methodology for the Synthesis of Nonsymmetric Glyceryl Diethers by a Tandem Acid-/Base-Catalyzed Process

TiO2 (Anatase) Nanoparticles a Novel Catalyst for Synthesis of vic-Diacetates as Biologically Active Compounds

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Zirconyl triflate, [ZrO(OTf)2], as a new and highly efficient catalyst for ring-opening of epoxides

Cited by 14 publications

References 42 publications

Enhancing the Regioselectivity of B(C6F5)3-Catalyzed Epoxide Alcoholysis Reactions Using Hydrogen-Bond Acceptors

Enhancing the Regioselectivity of B(C6F5)3-Catalyzed Epoxide Alcoholysis Reactions Using Hydrogen-Bond Acceptors

Readily Scalable Methodology for the Synthesis of Nonsymmetric Glyceryl Diethers by a Tandem Acid-/Base-Catalyzed Process

TiO2 (Anatase) Nanoparticles a Novel Catalyst for Synthesis of vic-Diacetates as Biologically Active Compounds

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Enhancing the Regioselectivity of B(C₆F₅)₃-Catalyzed Epoxide Alcoholysis Reactions Using Hydrogen-Bond Acceptors

Enhancing the Regioselectivity of B(C₆F₅)₃-Catalyzed Epoxide Alcoholysis Reactions Using Hydrogen-Bond Acceptors