134108-92-2Relevant articles and documents
Chelation-Controlled Protocol for the Diastereoselective Reduction of Ketones
Sarko, Christopher R.,Guch, Ian C.,DiMare, Marcello
, p. 705 - 706 (1994)
A new chelation-controlled, α-chiral ketone reduction protocol is presented based on titanium tetrachloride and a wide variety of reducing agents.Features of the proposed intermediate titanium chelates necessary to obtain high diastereoselectivity are dis
Efficient procedures for the large-scale preparation of (1S,2S)-trans-2-methoxycyclohexanol, a key chiral intermediate in the synthesis of tricyclic β-lactam antibiotics
Stead, Paul,Marley, Hugh,Mahmoudian, Mahmoud,Webb, Graham,Noble, David,Ip, Yam To,Piga, Elisabetta,Rossi, Tino,Roberts, Stanley,Dawson, Michael J.
, p. 2247 - 2250 (1996)
Enzymatic and chemical resolution methods suitable for preparation of multi-kg quantities of (+)-(1S,2S)-2-methoxycyclohexanol from (+/-) trans-2-methoxycyclohexanol have been developed. The enzymatic resolution was found to offer a particularly simple pr
Cross-linked poly(N-vinylpyrrolidone)-titanium tetrachloride complex: A novel stable solid TiCl4 equivalent as a recyclable polymeric Lewis acid catalyst for regioselective ring-opening alcoholysis of epoxides
Rahmatpour, Ali,Sajjadinezhad, Seyed Mehrzad
, (2021/08/09)
Cross-linked poly(N-vinylpyrrolidone) resin beads were prepared as macromolecular ligand precursors by suspension copolymerization of N-vinyl-2-pyrrolidone and N,N′-methylenebisacrylamide (MBA) as a crosslinking agent in water. Subsequently, the resulting polymer carrier precursor was readily combined with titanium tetrachloride to form a stable polymeric coordination complex (PNVP/TiCl4), and this novel stable TiCl4 equivalent evaluated as a heterogeneous and reusable solid Lewis acid catalyst for the regio-and stereoselective nucleophilic ring opening of various epoxides with various alcohols to prepare β-alkoxy alcohols in excellent yields without generating any waste. The MBA-cross-linked PNVP and resultant catalyst were characterized by Fourier transform infrared spectroscopy (FT–IR), field-emission scanning electron microscope (FE–SEM), energy dispersive X-ray (EDX), inductively coupled plasma (ICP), and thermogravimetric analysis (TGA) techniques. Moreover, the catalyst is very stable, easily separated, and reused at least five times without significant loss of activity. In terms of scope, yields, the amount of catalyst used, and reaction time, the PNVP-TiCl4 complex catalyst is an improvement over previously reported heterogeneous catalysts for ring opening of epoxides methods. Further, the experimental outcome revealed that using the copolymer beads as carriers with a high percentage of crosslinking and the high mesh size leads had an adverse effect on the reaction rate.
MBA-cross-linked poly(N-vinyl-2-pyrrolidone)/ferric chloride macromolecular coordination complex as a novel and recyclable Lewis acid catalyst: Synthesis, characterization, and performance toward for regioselective ring-opening alcoholysis of epoxides
Rahmatpour, Ali,Zamani, Maryam
, (2021/09/30)
A novel macromolecular-metal coordination complex, MBA-cross-linked PNVP/FeCl3 material was fabricated by immobilization of water intolerant ferric chloride onto the porous cross-linked poly(N-vinyl-2-pyrrolidone) carrier beads as a macromolecular ligand or carrier which was prepared by suspension free-radical copolymerization of N-vinyl-2-pyrrolidone (NVP) and N,N′-methylene bis-acrylamide (MBA) as a crosslinking agent in water. The obtained PNVP/FeCl3 was characterized by UV/vis and FT-IR spectroscopies, TGA, FE-SEM, EDX, and ICP techniques. This heterogenized version of ferric chloride is a convenient and safe alternative to highly water intolerant ferric chloride. The catalytic performance of (PNVP/FeCl3) as an efficient and recyclable polymeric Lewis acid catalyst was appropriately probed in the regio-and stereoselective nucleophilic ring opening of various epoxides with various alcohols in excellent yields with TOF up to 182.48 h?1 without generating any waste. The activity data indicate that this heterogeneous catalyst is very active and could be easily recovered, and reused at least six times without appreciable loss of activity indicating its stability under experimental conditions.
The charge-assisted hydrogen-bonded organic framework (CAHOF) self-assembled from the conjugated acid of tetrakis(4-aminophenyl)methane and 2,6-naphthalenedisulfonate as a new class of recyclable Br?nsted acid catalysts
Belokon, Yuri N.,Dmitrienko, Artem O.,Gak, Alexander S.,Gerasimov, Igor S.,Kuznetsova, Svetlana A.,Larionov, Vladimir A.,Li, Han,Medvedev, Michael G.,Nelyubina, Yulia V.,North, Michael,Saghyan, Ashot S.,Smol'yakov, Alexander F.,Zhereb, Vladimir P.
supporting information, p. 1124 - 1134 (2020/07/10)
The acid–base neutralization reaction of commercially available disodium 2,6-naphthalenedisulfonate (NDS, 2 equivalents) and the tetrahydrochloride salt of tetrakis(4-aminophenyl)methane (TAPM, 1 equivalent) in water gave a novel three-dimensional charge-assisted hydrogen-bonded framework (CAHOF, F-1). The framework F-1 was characterized by X-ray diffraction, TGA, elemental analysis, and 1H NMR spectroscopy. The framework was supported by hydrogen bonds between the sulfonate anions and the ammonium cations of NDS and protonated TAPM moieties, respectively. The CAHOF material functioned as a new type of catalytically active Br?nsted acid in a series of reactions, including the ring opening of epoxides by water and alcohols. A Diels–Alder reaction between cyclopentadiene and methyl vinyl ketone was also catalyzed by F-1 in heptane. Depending on the polarity of the solvent mixture, the CAHOF F-1 could function as a purely heterogeneous catalyst or partly dissociate, providing some dissolved F-1 as the real catalyst. In all cases, the catalyst could easily be recovered and recycled.
Fiber-supported Fe(iii) complex catalyst in spinning basket reactor for cleaner ring-opening of epoxides with alcohols
Shi, Xian-Lei,Sun, Benyu,Hu, Qianqian,Chen, Yongju,Duan, Peigao
, p. 3573 - 3582 (2019/07/09)
Herein, a newly designed fiber-supported iron catalyst was successfully synthesized by rooting diamine ligands into the surface layer of commercially available polyacrylonitrile fiber and then utilizing the diamine groups to immobilize Fe(iii) ions for heterogeneous catalytic ring-opening reactions. The resulting materials were characterized and observed in detail by elemental analysis, mechanical properties, FTIR spectroscopy and morphology during both the preparation and the utilization processes. Moreover, the fiber catalyst was used in the spinning basket reactor-mediated ring-opening of various epoxides by a series of alcohols under mild reaction conditions, giving good to quantitative yields of the corresponding β-alkoxy alcohols. In addition, the fiber catalyst in the impellers of the agitation system was shown to be reusable multiple times without leaching of the Fe(iii) ions, and when stored on the shelf remained equally active for at least three months. Furthermore, the catalytic system was convenient and effective for scaling-up experiments and thereby has prospects in industrial applications.
Synthesis and structure of an air-stable bis(pentamethylcyclopentadienyl) zirconium pentafluorbezenesulfonate and its application in catalytic epoxide ring-opening reactions
Li, Ningbo,Wang, Lingxiao,Wang, Haojiang,Qiao, Jie,Zhao, Wenjie,Xu, Xinhua,Liang, Zhiwu
, p. 1033 - 1039 (2018/02/06)
An air-stable mononuclear complex of bis(pentamethylcyclopentadienyl) zirconium pentafluorbezenesulfonate was successfully synthesized by treating C6F5SO3Ag with [(CH3)5Cp]2ZrCl2, which showed the cationic uninuclear structure of [{(CH3)5Cp}2Zr(CH3CN)2(H2O)][OSO2C6F5]2·CH3CN (1) confirmed by the X-ray analysis. Complex 1 was also characterized by other techniques and found to have the good nature of air-stability, water tolerance, thermally-stability and strong Lewis-acidity. Moreover, the complex showed high catalytic activity and recyclability in catalytic epoxide ring-opening reactions by amines or alcohols. This catalytic system affords a simple and efficient approach for synthesis of β-amino alcohols or β-alkoxy alcohols.
Introduction of an effective and economical heterogeneous ruthenium catalyst for regioselective ring-opening of epoxides and the friedel-crafts alkylation reaction of indoles and pyrroles
Tabatabaeian, Khalil,Zanjanchi, Mohammad Ali,Mahmoodi, Nosrat O.,Eftekhari, Tooraj
, p. 207 - 217 (2017/06/21)
Background: Metal organic frameworks square measure crystalline materials with fascinating chemical and physical attributes that include metal ions or clusters and multidentate organic particles. MOFs acquire the expected traits to be employed in classical applications similar to heterogeneous catalysis and storage and separation of gases and different Compounds. Post-synthetic modification (PSM) is an associate replacement method to prepare functionalized MOFs. Methods: The IRMOF-3-PI-RuCl3 was prepared by refluxing a combination of IRMOF-3-PI, [H(DMSO)2][RuCl4(DMSO)2] and ethanol. The amount of ruthenium metal in catalyst was found to be 2.35 w% based on ICP analysis. To perform the ring opening reaction, a solution of styrene oxide, indole, pyrole or alcohol nucleophile, in methanol, IRMOF-3-PI-RuCl3 was added. After completion of the reaction, the catalyst was precipitated. Results: A MOF-supported metal catalyst (IRMOF-3-PI-RuCl3) was designed and synthesized by postsynthetic method. The BET surface area of the final catalyst was slightly reduced as determined by N2 sorption experiments. The results showed that the provided catalyst has a high potential for the ring opening of epoxides with alcohols, indoles and pyrroles under gentle conditions. Conclusion: In summary, a simple, rapid, economical and an effective route for the alcoholysis of epoxides and therefore the Friedel-Crafts alkylation of indoles and pyrroles via an basically regioselective ring opening of epoxides with aliphatic and aromatic amines using IRMOF-3-PI-RuCl3 with cage type poriferous structure as heterogeneous catalysts, has been established. This methodology is very regioselective in numerous instances that give the products with high yield for e.g. in aromatic and aliphatic amines. Ease of separation and straightforward workup are among other advantages of this catalyst.
A highly efficient protocol for regioselective ring-opening of epoxides with alcohols, water, acetic acid, and acetic anhydride catalyzed by SbF3
Zeynizadeh, Behzad,Gilanizadeh, Masumeh,Aminzadeh, Farkhondeh Mohammad
, p. 1051 - 1056 (2016/07/06)
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.
Design and preparation of a polymer resin-supported organoselenium catalyst with industrial potential
Wang, Yuguang,Yu, Lihua,Zhu, Bingchun,Yu, Lei
, p. 10828 - 10833 (2016/07/21)
Hexavalent Se? Yes! Selenium on polymers exhibits quite different properties compared to that in small molecules. Hexavalent Se, rare in organoselenium chemistry, was found to be the major species on polymers. The high-valent Se species on recyclable polymer resins could quickly catalyze the oxidation reaction of cyclohexene with H2O2 in water to produce industrially important intermediate trans-1,2-cyclohexanediol in almost quantitative yield. In the catalytic cycle, high valent Se species were reduced to divalent Se, a highly activated species that could be re-oxidized by air so that no excess H2O2 was required for the reaction. The results were superior to those of reactions catalyzed by small molecules, for which excess H2O2, long reaction time or expensive CF3-activated catalysts and environmentally unfriendly MeCN solvent were required.
