52129-03-0Relevant articles and documents
Ultrasound Assisted the Synthesis of 1,3-Dioxolane Derivatives from the Reaction of Epoxides or 1,2-Diols with Various Ketones Using Graphene Oxide Catalyst
Mirza-Aghayan, Maryam,Mohammadi, Marzieh,Ahmadi, Zahra,Boukherroub, Rabah
, p. 2959 - 2969 (2020/04/22)
Abstract: The main objective of this study concerns the sonochemical synthesis of 1,3-dioxolane derivatives using graphene oxide catalyst by applying two methods. In the first method, we described the synthesis of 1,3-dioxolane by ring-opening of epoxides in the presence of ketones catalyzed by graphene oxide (GO) under ultrasonic irradiation. In the second sonochemical procedure, we described the synthesis of 1,3-dioxolane derivatives by the reaction of 1,2-diols with ketones using same GO catalyst. Mild reaction conditions, high yields, short reaction times, reusability of catalyst and easy isolation of the products make the developed methods very useful. Graphic Abstract: [Figure not available: see fulltext.]
Controlling Selectivity in Alkene Oxidation: Anion Driven Epoxidation or Dihydroxylation Catalysed by [Iron(III)(Pyridine-Containing Ligand)] Complexes
Tseberlidis, Giorgio,Demonti, Luca,Pirovano, Valentina,Scavini, Marco,Cappelli, Serena,Rizzato, Silvia,Vicente, Rubén,Caselli, Alessandro
, p. 4907 - 4915 (2019/08/30)
A highly reactive and selective catalytic system comprising Fe(III) and macrocyclic pyridine-containing ligands (Pc-L) for alkene oxidation by using hydrogen peroxide is reported herein. Four new stable iron(III) complexes have been isolated and characterized. Importantly, depending on the anion of the iron(III) metal complex employed as catalyst, a completely reversed selectivity was observed. When X=OTf, a selective dihydroxylation reaction took place. On the other hand, employing X=Cl resulted in the epoxide as the major product. The reaction proved to be quite general, tolerating aromatic and aliphatic alkenes as well as internal or terminal double bonds and both epoxides and diol products were obtained in good yields with good to excellent selectivities (up to 93 % isolated yield and d.r.=99 : 1). The catalytic system proved its robustness by performing several catalytic cycles, without observing catalyst deactivation. The use of acetone as a solvent and hydrogen peroxide as terminal oxidant renders this catalytic system appealing.
Convenient method for the transformation of epoxide to aldehyde and acetonide mediated by Cr-PLM
Chareonsiriwat, Laddawan,Chavasiri, Warinthorn
, p. 257 - 267 (2017/02/10)
Chromium-pillared montmorillonite (Cr-PLM) could be synthesized and efficiently utilized for styrene oxide transformations. The target aldehyde product could be quantitatively achieved from the isomerization of styrene oxide by using 10 wt% of Cr-PLM under reflux temperature for 15 min. The acetonide product could be achieved in excellent yield from the reaction of styrene oxide and acetone by using 10 wt% of Cr-PLM under room temperature for 20 min. The catalyst could be recovered and reused at least five times without loss of activity.
Iron oxide-pillared clay catalyzed the synthesis of acetonides from epoxides
Trikittiwong, Piyarat,Sukpirom, Nipaka,Shimazu, Shogo,Chavasiri, Warinthorn
, p. 104 - 107 (2015/03/18)
FeOx-pillared clays (FeOx-pillared bentonite, FeOx-pillared hectorite and FeOx-pillared taeniolite) were synthesized by the intercalation of FeCl3 into clay interlayers and calcination. The synthesize
Iron oxide-pillared clay catalyzed the synthesis of acetonides from epoxides
Trikittiwong, Piyarat,Sukpirom, Nipaka,Shimazu, Shogo,Chavasiri, Warinthorn
, p. 104 - 107 (2014/07/08)
FeOx-pillared clays (FeOx-pillared bentonite, FeOx-pillared hectorite and FeOx-pillared taeniolite) were synthesized by the intercalation of FeCl3 into clay interlayers and calcination. The synthesize
H2TPP organocatalysis in mild and highly regioselective ring opening of epoxides to halo alcohols by means of halogen elements
Torabi, Parviz,Azizian, Javad,Zomorodbakhsh, Shahab
scheme or table, p. 5508 - 5519 (2012/08/28)
We found that elemental iodine and bromine are converted to trihalide nucleophiles (triiodine and tribromide anion, respectively) in the presence of catalytic amounts of meso-tetraphenylporphyrins (H2TPP). Therefore a highly regioselective method for the synthesis of β-haloalcohols through direct ring opening of epoxides with elemental iodine and bromine in the presence of H2TPPs as new catalysts is described. At room temperature a series of epoxide derivatives were converted into the corresponding halohydrins resulting from an attack of trihalide species anion atoms at the less substituted carbon atom. This method occurs under neutral and mild conditions with high yields in various aprotic solvents, even when sensitive functional groups are present.
Indium(III) triflate catalysed transacetalisation reactions of diols and triols under solvent-free conditions
Smith, Brendan M.,Kubczyk, Tomasz M.,Graham, Andrew E.
experimental part, p. 7775 - 7781 (2012/09/21)
Acyclic acetals and ketals undergo transacetalisation in the presence of catalytic quantities of indium(III) triflate (In(OTf)3) and diols or triols under solvent-free conditions to generate the corresponding cyclic acetals and ketals in excellent yield. The methodology has been further developed to encompass a tandem acetalisation-acetal exchange protocol, which provides a facile and high yielding route to cyclic ketals from unreactive ketones under very mild reaction conditions.
Modular monodentate oxaphospholane ligands: Utility in highly efficient and enantioselective 1,4-diboration of 1,3-dienes
Schuster, Christopher H.,Li, Bo,Morken, James P.
supporting information; body text, p. 7906 - 7909 (2011/10/09)
Tune it up! Tunable, chiral, monodentate oxaphospholane ligands (termed OxaPhos) are highly effective in the Pt-catalyzed title reaction, providing the 1,4-addition products in enantiomer ratios approaching 99:1 (see scheme). In the presence of enantiomerically pure cis-iBu-OxaPhos, a catalyst loading of only 0.02 mol% [Pt(dba)3] was sufficient for effective reaction. pin=pinacolato, dba=dibenzylideneacetone.
Gold-catalysed activation of epoxides: Application in the synthesis of bicyclic ketals
Balamurugan, Rengarajan,Kothapalli, Raveendra Babu,Thota, Ganesh Kumar
experimental part, p. 1557 - 1569 (2011/04/25)
Gold-catalysed generation of diol equivalents from epoxides and their intramolecular reaction with Ca≡C bonds to generate bicyclic ketals is presented. This reaction essentially involves the formation of an acetonide, which subsequently cyclises on the alkyne intramolecularly under gold catalysis conditions. This method could be extended to make optically pure bicyclic ketals. Deuterium incorporation experiments were carried out to ascertain the mechanism of the reaction. Sequential activation of epoxide and alkyne moieties by a gold catalyst in acetone as solvent has been achieved. This strategyhas been employed to synthesise bicyclic ketals from epoxy alkynes. Copyright
Investigation of the catalytic activity of an electron-deficient vanadium(IV) tetraphenylporphyrin: A new, highly efficient and reusable catalyst for ring-opening of epoxides
Taghavi, S. Abdolmanaf,Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Tangestaninejad, Shahram,Mirkhani, Valiollah,Khosropour, Ahmad Reza,Ahmadi, Venus
experimental part, p. 2244 - 2252 (2011/10/03)
In this work, the catalytic activity of high-valent tetraphenylporphyrinatovanadium(IV) trifluoromethanesulfonate, [V IV(TPP)(OTf)2], in the nucleophilic ring-opening of epoxides is reported. This new V(IV) catalyst was used as an efficient catalyst for alcoholysis with primary (methanol, ethanol and n-propanol), secondary (iso-propanol) and tertiary alcohols (tert-butanol), hydrolysis and acetolysis of epoxides with acetic acid and also for the conversion of epoxides to 1,2-diacetates with acetic anhydride, conversion of epoxides to thiiranes with ammonium thiocyanate and thiourea, and for conversion of epoxides to acetonides with acetone. The catalyst was reused several times without loss of its activity.
