- Application of poly(Vinylbenzyltrimethylammonium tribromide) resin as an efficient polymeric catalyst in the acetalization and diacetylation of benzaldehydes
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The applications of a new supported tribromide reagent (poly(vinylbenzyltrimethylammonium tribromide) resin) were reported. This supported tribromide resin was used as a catalyst in the acetalization and diacetylation of benzaldehydes under mild conditions with high efficiency. The effects of solvents, and amount of the supported tribromide resin on the reactions were investigated. Under the optimal conditions, most of acetal and 1,1-diacetates of benzaldehydes were selectively obtained in excellent yields.
- Han, Bingbing,Hu, Junjun,Li, Xianwei,Zheng, Zubiao
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supporting information
p. 287 - 293
(2021/04/28)
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- Inhibition by Water during Heterogeneous Br?nsted Acid Catalysis by Three-Dimensional Crystalline Organic Salts
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A new self-assembled and self-healing class of metal free, recyclable, heterogeneous Br?nsted acid catalysts has been developed by the protonation of aniline derivatives (tetrakis(4-aminophenyl)methane, leuco-crystal violet, benzidine, and p-phenylenediamine) with aromatic sulfonic acids (tetrakis(phenyl-4-sulfonic acid)methane, and 2,6-naphthalenedisulfonic acid). As a result, five three-dimensional crystalline organic salts (F-1a, F-1b, F-1c, F-2, and F-3) were obtained, linked by hydrogen bonds and additionally stabilized by the opposite charges of the components. Frameworks F-2 and F-3 were prepared for the first time and characterized by elemental analysis, X-ray structural analysis (for F-2), thermogravimetry, SEM, and FTIR spectroscopy. The catalytic activities of crystalline organic salts F-1-3 have been explored in industrially important epoxide ring-opening and acetal formation reactions. The presence of encapsulated water inside frameworks F-1a and F-2 had an inhibitory effect on the performance of the catalysts. X-ray diffraction analysis of hydrated and dehydrated samples of F-1a and F-2 indicated that water of crystallization served as a cross-linking agent, diminishing the substrate induced "breathing"affinities of the frameworks.
- Belokon, Yuri N.,Gak, Alexander,Khakina, Ekaterina,Khrustalev, Victor N.,Korlyukov, Alexander A.,Kuznetsova, Svetlana,Li, Han,Lobanov, Nikolai,Nelyubina, Yulia,North, Michael,Peregudov, Alexander S.,Riazanov, Vladimir,Zhereb, Vladimir
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p. 6364 - 6372
(2021/10/20)
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- Design and synthesis of a novel series of cyanoindole derivatives as potent γ-secretase modulators
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The discovery, design and synthesis of a new series of GSMs is described. The classical imidazole heterocycle has been replaced by a cyano group attached to an indole nucleus. The exploration of this series has led to compound 26-S which combined high in
- Bischoff, Fran?ois P.,Velter, Adriana Ingrid,Minne, Garrett,Pieters, Serge,Berthelot, Didier,De Cleyn, Michel,Gijsen, Harrie J.M.,Macdonald, Gregor,Surkyn, Michel,Van Brandt, Sven,Van Roosbroeck, Yves,Zavattaro, Chiara,Mercken, Marc,Austin, Nigel,Dhuyvetter, Deborah,Borghys, Herman,Ahmad, Ishtiyaque,Samanta, Swapan Kumar
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p. 1737 - 1745
(2019/05/22)
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- House bulb light-induced photochemical acetalization of carbonyl compounds catalyzed by Eosin Y
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We have systematically studied the reactions of acetalization and found that high reaction efficiency can be achieved using cheap and readily available organic Eosin Y as catalyst. The reaction proceeds smoothly under house bulbs and shows excellent functional group tolerance. The substrates of the reaction system are compatible with aromatic aldehydes, aliphatic aldehydes, aromatic ketones, and cyclic ketones with high yields.
- Zhou, Quan,Jia, Tao,Li, Xiao-Xuan,Zhou, Lin,Li, Chang-Jiang,Feng, Yi-Si
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supporting information
p. 1068 - 1075
(2018/05/23)
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- New Br?nsted-Lewis acidic quaternary ammonium ionic liquids: Synthesis, acidity determination and acidity-catalytic activity relationship
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A series of new Br?nsted-Lewis acidic ionic liquids, which are operational simplicity, high stability, low cost and applicable for scaling up, have been synthesized and their activity for acetalization was examined. The comprehensive studies on the acidity-catalytic performance relationship of the Br?nsted-Lewis acidic ionic liquids were performed. IR spectroscopy results confirmed that the new Br?nsted-Lewis acidic ionic liquids possess both Br?nsted and Lewis acid sites. The acidities were determined by Hammett method, and further studies on acidity-activity relationship revealed that the acidity played a key role in the acid-catalyzed probe reactions.
- Yi, Fengping,Gao, Jie,Zhang, Lirong,Jiang, Xiaoyan
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p. 1260 - 1264
(2015/02/19)
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- Synthesis and characterization of a tetracationic acidic organic salt and its application in the synthesis of bis(indolyl)methanes and protection of carbonyl compounds
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A new tetracationic acidic organic salt (TCAOS) based on DABCO was prepared, characterized and applied as an eco-friendly, powerful and reusable catalyst for the synthesis of bis(indolyl)methanes from indoles and carbonyl compounds in water with high turnover frequency (TOF). Also, this catalyst was successfully applied for acetalization of carbonyl compounds with diols under solvent-free conditions.
- Halimehjani, Azim Ziyaei,Hooshmand, Seyyed Emad,Shamiri, Elham Vali
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p. 21772 - 21777
(2015/03/18)
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- Acetalization of aldehydes and ketones over H4[SiW 12O40] and H4[SiW12O 40]/SiO2
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H4[SiW12O40] (H-SiW12) is demonstrated to be able to efficiently catalyze the acetalization of aldehydes and ketones with ethylene glycol and 1,3-propanediol. Nevertheless, the possible leaching and the recycling of H-SiW12 are two major disadvantages that largely restrict its further application in industry. Moreover, H 4[SiW12O40] tends to deactivate strong proton sites due to the small surface area of 10 m2 g-1. Due to interactions with surface silanol groups, the proton sites of polyoxometalates (POMs) on SiO2 are less susceptible to deactivation. As such, immobilization of H4[SiW12O40] onto SiO 2 leads to the heterogeneous catalyst H4[SiW 12O40]/SiO2 (H-SiW12/SiO 2), which can catalyze the acetalization of aldehydes and ketones with ethylene glycol and 1,3-propanediol selectively and efficiently without the need of a drying agent. The acetalization process can proceed smoothly at a relatively low temperature under solvent-free conditions. The catalyst of H 4[SiW12O40]/SiO2 can be recycled at least ten times without an obvious decrease in its catalytic activity. As far as we know, the TONs of the H-SiW12/SiO2-catalyzed acetalization of cyclohexanone with ethylene glycol, and benzaldehyde with 1,3-propanediol are the highest reported so far.
- Zhao, Shen,Jia, Yueqing,Song, Yu-Fei
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p. 2618 - 2625
(2014/07/22)
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- A facile and efficient protocol for esterification and acetalization in a PEG1000-D(A)IL/toluene thermoregulated catalyst-media combined systems
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A novel efficient and recyclable temperature-dependent biphasic catalyst and reaction media combined system comprised of PEG-1000 linked dicationic acidic ionic liquid and toluene was developed and applied in esterification of aromatic acids and acetalization of aromatic aldehydes with good to excellent yields. This system is characteristic of temperature-dependent reversible biphasic property, simple and facile recyclability, high catalytic activity and extensive substrate and reaction adaptability.
- Wang, Yinglei,Zhi, Huizhen,Luo, Jun
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- Facile aldolization catalyzed by ionic liquid [4-sulfbmpyrazine][BF 4]
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The acidic functionalized ionic liquid 1-(4-sulfonic group)butyl-3- methylpyrazine tetrafluoroborate (abbreviated as [4-sulfbmpyrazine][BF 4]) was employed as the catalyst of the condensation of aromatic aldehyde and diols. The optimized condition was as follows: aromatic aldehyde (0.20 mol), diols (0.30 mol) and [4-sulfbmpyrazine][BF4] (0.60 g) were refluxed in cyclohexane (10.00 mL) for 1 h. A series of aromatic aldehydes were studied and afforded the corresponding acetals products with good yields which were from 70.3 to 96.9 %. The ionic liquid catalyst could be recycled for four times without significant loss of catalyst reactivity.
- Zou, Jianzhong,Yi, Fengping,Zhang, Lirong,Wang, Zhen
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p. 6643 - 6646
(2013/07/26)
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- Homologative trifluoromethylation of acetals
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Trifluoroethyl α-insertion of acetals has been developed. Aromatic, heteroaromatic, and alkenyl acetals react with in situ generated (trifluoromethyl)diazomethane in the presence of antimony(V) chloride to furnish α-trifluoromethyl acetals. A stereoselective version of this transformation exploiting the acetal as a chiral auxiliary is also presented. Georg Thieme Verlag Stuttgart · New York.
- Hamilton, James Y.,Morandi, Bill,Carreira, Erick M.
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p. 1857 - 1862
(2013/07/26)
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- Bismuth compounds in organic synthesis: Synthesis of dioxanes, dioxepines, and dioxolanes catalyzed by bismuth(III) triflate
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A simple method for the synthesis of 1,3-dioxolanes from carbonyl compounds has been developed using 1,2-bis(trimethylsilyloxy)ethane in the presence of bismuth(III) triflate as a catalyst. The bismuth(III) triflate catalyzed synthesis of a range of dioxanes and dioxepines has also been developed. In these latter cases, the carbonyl compound is treated with a diol, and triethyl orthoformate is used as a water scavenger. All these methods avoid the use of a Dean-Stark trap. Georg Thieme Verlag Stuttgart.
- Podgorski, Daniel M.,Krabbe, Scott W.,Le, Long N.,Sierszulski, Paul R.,Mohan, Ram S.
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experimental part
p. 2771 - 2775
(2010/10/02)
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- Acetalization of carbonyl compounds catalyzed by bismuth triflate under solvent-free conditions
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Carbonyl compounds were converted to the corresponding 1,3-dioxolanes and 1,3-dioxanes with ethylene glycol and 1,3-propandiol in the presence of bismuth triflate under solvent-free conditions. In addition, high chemoselective protection of aldehydes in the presence of ketones has been achieved.
- Aliyan, Hamid,Fazaeli, Razieh,Massah, Ahmad Reza,Momeni, Ahmad Reza,Naghash, Hamid Javaherian,Moeinifard, Behzad
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experimental part
p. 873 - 876
(2012/04/05)
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- Highly efficient and chemoselective acetalization of carbonyl compounds catalyzed by new and reusab e zirconyl triflate, zr0(0tf)2
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Various types of aromatic aldehydes were efficiently converted to their corresponding 1,3-dioxanes and 1,3-dioxolane with 1,3-propanediol and ethylene glycol, respectively, in the presence of catalytic amount of ZrO(OTf) 2 in acetonitrile at room temperature. The catalyst can be reused several times without loss of its catalytic activity. Very short reaction times, selective acetalization of aromatic aldehydes in the presence of aliphatic aldehydes and ketones, very mild reaction conditions, reusability of the catalyst, and easy workup are noteworthy advantages of this method.
- Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Tangestaninejad, Shahram,Mirkhani, Valiollah,Yazdani, Parvin,Ghorjipoor, Saeedeh
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experimental part
p. 131 - 135
(2009/09/30)
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- Intermolecular reactions of chlorohydrine anions: Acetalization of carbonyl compounds under basic conditions
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Nonenolizable aldehydes and ketones react with 2-chloroethanol and 3-chloropropanol under basic conditions (t-BuOK, DMF/THF) with formation of 2-substituted 1,3-dioxolanes and 1,3-dioxanes, respectively. Conversion of the two-step addition-alkylation process depends on the electrophilicity of the carbonyl group that governs the equilibrium of addition of chloroalkoxides. This method of protection of carbonyl groups in the form of cyclic acetals under kinetically controlled conditions is complementary to the acid-catalyzed reaction with diols.
- Barbasiewicz, Michal,Makosza, Mieczyslaw
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p. 3745 - 3748
(2007/10/03)
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- An efficient route to biaryls from aryl halides catalysed by subnanometrical 2,2′-bipyridine liganded Ni-Al clusters
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It has been shown that the new 2,2′-bipyridine liganded Ni-Al bimetallic clusters are efficient in promoting the catalytic homocoupling of (het)aryl chlorides and bromides.
- Massicot, Fabien,Schneider, Rapha?l,Fort, Yves,Illy-Cherrey, Sandra,Tillement, Olivier
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p. 531 - 536
(2007/10/03)
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- Silica gel-supported metallic sulfates catalyzed chemoselective acetalization of aldehydes under microwave irradiation
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Silica gel - supported metallic sulfates are found to be efficient catalysts for the protection of both aromatic and aliphatic aldehydes as 1,3- dioxolanes under microwaves in solvent-free conditions. Due to the neutral reaction conditions, this method is compatible with acid sensitive substrates.
- Yadav,Reddy, B. V. Subba,Srinivas,Ramalingam
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p. 701 - 703
(2007/10/03)
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- Naphthalene-catalysed lithiation of 2-(chlorophenyl)-1,3-dioxolanes: Generation of formyl- and acetyl-phenyllithium equivalents [1]
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The reaction of 2-(chlorophenyl)-1,3-dioxolanes 1 with an excess of lithium powder and a catalytic amount of naphthalene (5 mol %) in the presence of different carbonyl compounds [(t)BuCHO, Et2CO, (CH2)5CO, PhCOMe] as elec
- Huerta, Fernando F.,Gomez, Cecilia,Yus, Miguel
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p. 4043 - 4050
(2007/10/03)
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