- An immobilized organocatalyst for cyanosilylation and epoxidation
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An immobilized organocatalyst has been synthesized by covalently anchoring an N-octyldihydroimidazolium hydroxide fragment onto SiO2 (denoted as 1-OH/SiO2). This catalyst exhibits high catalytic performance for the cyanosilylation of
- Yamaguchi, Kazuya,Imago, Toru,Ogasawara, Yoshiyuki,Kasai, Jun,Kotani, Miyuki,Mizuno, Noritaka
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- Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP): Efficient catalysts for the cyanosilylation and cyanocarbonation of aldehydes and ketones
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A variety of aldehydes and ketones were transformed to their corresponding cyanohydrin silyl ethers in good to excellent yields in the presence of 1-5 mol% of tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP). Cyanohydrin carbonates were also readily prepared using 5-10 mol% of TTMPP as an organocatalyst.
- Matsukawa, Satoru,Sekine, Izumi,Iitsuka, Ayumi
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- A direct and efficient synthetic method for nitriles from ketones
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Cyclic cyano derivatives 3 were obtained by the reaction of Me3SiCN / ZnI2 with the cyclic ketones 2 which gave the trimethylsilyloxy nitriles 4. They were directly transformed to cyano derivatives 3 (70-80% yield) by the reductive reagent Me3SiCl-NaI in acetonitrile in the presence of H2O.
- Kloubert, Stephane,Mathe-Allainmat, Monique,Andrieux, Jean,Langlois, Michel
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- Niobium fluoride (NbF5): A highly efficient catalyst for solvent-free cyanosilylation of aldehydes
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An efficient method for the addition of trimethylsilylcyanide (TMSCN) to aldehydes using dispersed NbF5 as the catalyst is described. Cyano transfer from TMSCN to aldehydes occurs within 10 minutes at room temperature in the presence of 0.5 mol
- Sung, Soo Kim,Rajagopal, Gurusamy
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- Addition of trimethylsilyl cyanide to aromatic ketones promoted by organic solutions of lithium salts
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Cyanosilylation of aromatic ketones is strongly promoted in organic solutions of specific lithium salts (perchlorate and tetrafluoroborate). Acetonitrile solutions of LiBF4 are safe and efficient media for this reaction.
- Jenner, Gerard
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- Remarkable Acceleration of Benzimidazole Synthesis and Cyanosilylation Reactions in a Supramolecular Solid Catalyst
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A solid metal–organic catalyst with hydrophobic pockets and Lewis acid centers strongly accelerates the reaction rate for organic reactions. This is exemplified for the cyanosilylation of ketones and for the synthesis of benzimidazoles, for which very hig
- Rojas-Buzo, Sergio,García-García, Pilar,Corma, Avelino
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- Enantioselective cyanosilylation of ketones catalyzed by double-activation catalysts with N-oxides
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Enantioselective addition of trimethylsilyl cyanide to ketones by a catalytic double-activation method is described. By combinatorially using 2.0 mol% of a chiral salen-titanium complex and 1.0 mol% of an achiral tertiary amine N-oxide, aromatic, aliphati
- Chen, Fu-Xue,Qin, Bo,Feng, Xiaoming,Zhang, Guolin,Jiang, Yaozhong
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- Trimethylsilylcyanation of heteroaromatic ketones in the CsF/18-crown-6/benzene phase-transfer catalytic system
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The trimethylsilylcyanation of heteroaromatic ketones in the Me3SiCN/CsF/18-crown-6/benzene phase-transfer catalytic system has been studied. The reaction products have been isolated selectively in yields of up to 95%. 1999 KluwerAcademic/Plenu
- Abele,Abele,Mazheika,Lukevics
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- SYNTHESIS OF α-HYDROXIAMIDES VIA THE CYANOSILYLATION OF AROMATIC KETONES
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The trimethylsilyl ethers of the cyanohydrins of aryl-alkyl ketones and diaryl ketones afforded the corresponding α-hydroxyamides upon hydrolysis with HCl or HNO3/HCO2H.The method is advantageous for ketones do not readily undergo addition of HCN.
- Grunewald, Gary L.,Brouillette, Wayne J.,Finney, Jay A.
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- Activation of TMSCN by N-heterocyclic carbenes for facile cyanosilylation of carbonyl compounds
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N-Heterocyclic carbenes were found to be highly effective organocatalysts in activating TMSCN for facile cyanosilylation of carbonyl compounds. Cyano transfer from TMSCN to aldehydes and ketones proceeds at room temperature in the presence of only 0.01-0.
- Song, Jinhua J.,Gallou, Fabrice,Reeves, Jonathan T.,Tan, Zhulin,Yee, Nathan K.,Senanayake, Chris H.
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- Chiral rare-earth metal complexes with a tridentate amido-fluorenyl ligand: Syntheses, structures and catalytic performance
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The complexes of rare-earth metals (Y, La, Sm and Lu) with a chiral tridentate amido-fluorenyl ligand were synthesized and characterized. These complexes demonstrated high efficiency in catalyzing both the intramolecular hydroamination of non-activated ol
- Chai, Zhuo,Wang, Yemei,Tang, Mujun,Mu, Xiaolong,Hou, Jinsong,Yang, Gaosheng
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- Hydrosilylation of ketone and imine over poly-N-heterocyclic carbene particles
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N-Heterocyclic carbene (NHC)-catalyzed ketone/imine hydrosilylation, silane alcohol condensation and asymmetric ketone hydrosilylation reactions were demonstrated for the first time over solid, main-chain poly-NHC particles. The stable and robust poly-NHC
- Tan, Meixuan,Zhang, Yugen,Ying, Jackie Y.
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- A Convenient One-Pot Cyanosilylation of Aldehydes and Ketones Using Potassium or Sodium Cyanide Impregnated on Amberlite XAD Resin and Trimethylsilyl Chloride
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In the cyanosylilation of benzaldehyde, the combination of potassium or sodium cyanide impregnated on Amberlite XAD resin and trimethylsilyl chloride has been found to be a good one-pot cyanosilylation agent.Although acetonitrile is the best solvent, subs
- Sukata, Kazuaki
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- Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis
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Cyanosilylation of carbonyl compounds provides protected cyanohydrins, which can be converted into many kinds of compounds such as amino alcohols, amides, esters, and carboxylic acids. In particular, the use of trimethylsilyl cyanide as the sole carbon source can avoid the need for more toxic inorganic cyanides. In this paper, we describe an electrochemically initiated cyanosilylation of carbonyl compounds and its application to a microflow reactor. Furthermore, to identify suitable reaction conditions, which reflect considerations beyond simply a high yield, we demonstrate machine learning-assisted optimization. Machine learning can be used to adjust the current and flow rate at the same time and identify the conditions needed to achieve the best productivity.
- Sato, Eisuke,Fujii, Mayu,Tanaka, Hiroki,Mitsudo, Koichi,Kondo, Masaru,Takizawa, Shinobu,Sasai, Hiroaki,Washio, Takeshi,Ishikawa, Kazunori,Suga, Seiji
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- Ligand-tailored single-site silica supported titanium catalysts: Synthesis, characterization and towards cyanosilylation reaction
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A successive anchoring of Ti(NMe2)4, cyclopentadiene and a O-donor ligand, 1-hydroxyethylbenzene (PEA), 1,1′-bi-2-naphthol (Binol) or 2,3-dihydroxybutanedioic acid diethyl ester (Tartrate), on silica was conducted by SOMC strategy in moderate conditions. The silica, monitored by in-situ Fourier transform infrared spectroscopy (in-situ FT-IR), was pretreated at different temperatures (200, 500 and 800 °C). The ligand tailored silica-supported titanium complexes were characterized by in-situ FT-IR, 13C CP MAS-NMR, X-ray photoelectron spectroscopy (XPS), X-ray absorption near edge structure (XANES) and elemental analysis in detail, verifying that the surface titanium species are single sited. The catalytic activity of the ligand tailored single-site silica supported titanium complexes was evaluated by a cyanosilylation of benzaldehyde. The results showed that the catalytic activity is dependent strongly on the dehydroxylation temperatures of silica and the configuration of the ligands.
- Xu, Wei,Li, Yani,Yu, Bo,Yang, Jindou,Zhang, Ying,Chen, Xi,Zhang, Guofang,Gao, Ziwei
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- Different acidity and additive effects of zirconium metal-organic frameworks as catalysts for cyanosilylation
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The Zr(iv) metal-organic framework with 1,4-benzenedicarboxylate (UiO-66) in different forms was studied as a solid catalyst for carbonyl cyanosilylation. The anhydrous material (UiO-66-A) obtained after calcination has open Lewis-acid sites and acts as a heterogeneous and size selective catalyst for the reaction of aldehydes and trimethylsilylcyanide (TMSCN). Notably, it was found that the as-synthesized hydrous form (UiO-66-H) shows comparable activity to UiO-66-A, so UiO-66 can be used as a catalyst for cyanosilylation with no need of high-temperature activation. With a number of intentionally designed control experiments, we demonstrated that the acetic acid enclosed in UiO-66-H during synthesis serves as a Bronsted acid to promote the reaction, though acetic acid is inactive by itself. The different acidity between UiO-66-H and UiO-66-A was confirmed by using the isomerization of α-pinene oxide as a probe reaction. Both UiO-66-H and UiO-66-A are recyclable without significant degradation in framework integrity and catalytic activity. In addition, it was unexpectedly found that pyridine, which is inactive alone, acts as co-catalyst, rather than a Lewis acid poison, to dramatically accelerate the catalytic reaction over UiO-66-H or UiO-66-A. A synergistic mechanism was suggested, in which the Lewis or Bronsted acid activates the aldehyde substrate while pyridine acts as a Lewis base to activate TMSCN.
- Xi, Fu-Gui,Yang, Yang,Liu, Hui,Yao, Hong-Fei,Gao, En-Qing
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- TBD-catalyzed cyanosilylation of aldehydes and ketones
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This study examines the catalytic efficacy of 1,5,7-triazabicyclo[4,4,0]dec-5-ene (TBD) in the cyanosilylation of aldehydes and ketones. In an aldehyde reaction, the corresponding products were obtained at high yield using minimal TBD (0.01 mol%). TBD was
- Matsukawa,Kimura
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- Low-valent magnesium(i)-catalyzed cyanosilylation of ketones
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The magnesium(i) complex [(XylNacnac)Mg]2 was employed as a highly efficient catalyst for the cyanosilylation of a variety of ketones with trimethylsilyl cyanide under mild conditions. In contrast to the traditional stoichiometric us
- Wang, Weifan,Luo, Man,Li, Jia,Pullarkat, Sumod A.,Ma, Mengtao
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- Lewis Acid Rather than Bronsted Acid Sites of Montmorillonite K10 Act as a Powerful and Reusable Green Heterogeneous Catalyst for Rapid Cyanosilylation of Ketones
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A practical green protocol was developed for highly efficient cyanosilylation of various ketones catalyzed by commercial montmorillonite K10, with excellent isolated yields (91-99%). The catalyst can be used as received, and its catalytic strength can be
- Huang, Xiao,Chen, Lin,Ren, Fengying,Yang, Chen,Li, Jianghong,Shi, Kejin,Gou, Xiaojun,Wang, Wei
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- A dream combination for catalysis: Highly reactive and recyclable scandium(iii) triflate-catalyzed cyanosilylations of carbonyl compounds in an ionic liquid
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The catalytic activity of lanthanide triflates, particularly scandium triflate, increased dramatically in [bmim][SbF6], allowing the cyanosilylation of a variety of aldehydes and ketones with a turnover frequency up to 48000 mol h-1 and a total turnover number of 100000.
- Park, Boyoung Y.,Ryu, Ka Yeon,Park, Jung Hwan,Lee, Sang-Gi
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- Highly efficient cyanosilylation of aldehydes and ketones under microwave, solvent-free, and Lewis acid-free conditions
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The addition of TMSCN to aldehydes and ketones under microwave irradiation in the absence of any Lewis or Bronsted acid and solvent yielded the corresponding cyanohydrins in good yields in short reaction times (less than 30 min). Copyright Taylor & Francis Group, LLC.
- Iida, Hirokazu,Hamana, Hiroshi,Matsumoto, Kiyoshi
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- Crystal transformation in Mn(ii) metal-organic frameworks based on a one-dimensional chain precursor
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The solvothermal reaction of Mn(ii) salts and 5-((4′-(tetrazol-5′′-yl)benzyl)oxy)isophthalic acid (H3L) affords an Mn(ii) based coordination polymer Mn(H2L)2(H2O)2(1), which possesses a one-dimensiona
- Fan, Yong,Gong, Yiran,Jiang, Yansong,Liu, Rui,Wang, Li,Xu, Jianing
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p. 9540 - 9546
(2021/07/17)
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- Three Coordinated Organoaluminum Cation for Rapid and Selective Cyanosilylation of Carbonyls under Solvent-Free Conditions
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The well-defined three coordinated electronically unsaturated cationic organoaluminum complex [({(2,6-iPr2C6H3N)P(Ph2)}2N)AlMe]+[MeB(C6F5)3]? (1), has been utilized to catalyze the cyanosilylation of aldehydes and ketones under mild and solvent-free conditions. Moreover, catalyst 1 showed high chemoselective cyanosilylation of aldehydes over ketones, nitriles and olefins. The multinuclear NMR investigations revealed that cyanosilylation proceeds via Lewis adduct formation between 1 and TMSCN thereby activating TMSCN (Si-CN bond) followed by nucleophilic attack of the carbonyl oxygen at the Si center of the activated silane and formation of the product.
- Bhandari, Mamta,Prashanth, Billa,Rawat, Sandeep,Singh, Sanjay
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- Ultrathin Near-Infrared Light Activated Nano-Hotplate Catalyst
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A combined photothermal-catalytic system that contains a single active element, without using different entities for separate roles (catalytic vs photothermal), is designed here for efficient catalytic reactions. Herein, ultrathin (sub-6 nm) rectangular-l
- Wu, Xiangyang,Yeow, Edwin K. L.
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- Two polyoxoniobates-based ionic crystals as Lewis base catalysts for cyanosilylation
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Two transition-metal containing heteropolyniobates, H[Ni(en)3]5[VNb12O40(VO)2]·15H2O (1) and H3[Cu(en)2]4[VNb12O40(VO)2]·13
- Li, Shujun,Ji, Panpan,Han, Shangning,Hao, Zhaomin,Chen, Xuenian
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- Nanoceria as a recyclable catalyst/support for the cyanosilylation of ketones and alcohol oxidation in cascade
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The cyanosilylation of carbonyl compounds is a fundamental reaction in organic synthesis, to give cyanohydrins. Ketones are particularly reluctant to cyanosilane addition and require the action of a catalyst, and despite many soluble Br?nsted and Lewis ac
- Garnes-Portolés, Francisco,Leyva-Pérez, Antonio,Rivero-Crespo, Miguel ángel
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- Preparation and application of ammonium salt
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The invention discloses an ammonium salt. The structural formula of the ammonium salt is shown in the specification. A synthesizing method of the ammonium salt comprises the following steps: refluxingand carrying out reaction between 5 mmol of 1-phenyl-1,
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Paragraph 0011
(2019/07/04)
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- Cyanosilylation reaction method using hydroboron to catalyze ketone
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The invention relates to the field of organic chemistry, aiming at solving the problems that the existing ketone-catalyzing cyanosilylation reaction has the defects of complicated catalyst structure,high preparation cost and more application limitations,
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Paragraph 0022
(2018/05/03)
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- Syntheses, Structures, and Catalytic Activities of the Anionic Heterobimetallic Rare-Earth Metal Complexes Supported by Pyrrolyl-Substituted 1,2-Diimino Ligands
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A series of the anionic heterobimetallic rare-earth metal complexes supported by trans- or chiral pyrrolyl-substituted 1,2-diimino ligands were synthesized in good yields via reactions of [(Me3Si)2N]3RE(μ-Cl)Li(THF)3
- Wang, Wei,Wang, Xiaojia,Zhou, Shuangliu,Xu, Xiaolong,Du, Jun,Zhang, Lijun,Mu, Xiaolong,Wei, Yun,Zhu, Xiancui,Wang, Shaowu
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supporting information
p. 10390 - 10400
(2018/08/28)
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- Hydroboration, Cyanosilylation, and Sequential Cyanosilylation and Hydroboration of Carbonyl Compounds in the Presence of a TiIV Amido Complex as an Efficient Catalyst
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Catalytic hydroboration and cyanosilylation of a wide range of aldehydes and ketones, with pinacolborane (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) and trimethylsilyl cyanide, respectively, in the presence of titanium(IV) complexes [κ2-{(C5
- Harinath, Adimulam,Bhattcharjee, Jayeeta,Gorantla, Koteswar Rao,Mallik, Bhabani S.,Panda, Tarun K.
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supporting information
p. 3180 - 3192
(2018/07/06)
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- A cationic aluminium complex: An efficient mononuclear main-group catalyst for the cyanosilylation of carbonyl compounds
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A structurally characterized cationic aluminium complex [(AT)Al(DMAP)]+[OTf]- (3) stabilized through a relatively nonbulky aminotroponate (AT) ligand is reported (DMAP = 4-(dimethylamino)pyridine). This compound was found to work as
- Sharma, Mahendra Kumar,Sinhababu, Soumen,Mukherjee, Goutam,Rajaraman, Gopalan,Nagendran, Selvarajan
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supporting information
p. 7672 - 7676
(2017/07/11)
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- A chiral amide compound of preparation and synthetic method
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The invention relates to a chiral amide compound of which the chemical formula is disclosed in the chemical formula. The synthesis method of the chiral amide compound (I) is implemented by reacting 28.79 mmol of meta-cyanoaniline and 4.3058g of chiral D-phenylglycinol in 80ml of chlorobenzene under reflux in the presence of ZnCl2 under water-free oxygen-free conditions for 60-72 hours, wherein the ZnCl2 accounts for 33-100 mol% of the raw materials, preferably 99.4 mol%. The chiral amide compound has certain catalytic performance in benzaldehyde cyanosilicification reaction, Henry reaction and Baylis-Hillman reaction, and the conversion rates are respectively up to 87%, 50% and 33%.
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Paragraph 0244; 0245; 0246; 0247
(2017/04/29)
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- A copper-nitrogen complex
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The invention discloses a copper-nitrogen complex with a chemical formula (I) specified in the description. A synthesis method of the copper-nitrogen complex (I) comprises the following steps: reacting 3-hydroxypicolinamide with Cu(OAc)2.H2O in a molar ra
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Paragraph 0172; 0173; 0174; 0175; 0176; 0177
(2017/08/25)
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- Synchronizing Substrate Activation Rates in Multicomponent Reactions with Metal-Organic Framework Catalysts
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A study on the influence of the cation coordination number, number of Lewis acid centers, concurrent existence of Lewis base sites, and structure topology on the catalytic activity of six new indium MOFs, has been carried out for multicomponent reactions (MCRs). The new indium polymeric frameworks, namely [In8(OH)6(popha)6(H2O)4]·3 H2O (InPF-16), [In(popha)(2,2′-bipy)]·3 H2O (InPF-17), [In3(OH)3(popha)2(4,4′-bipy)]·4 H2O (InPF-18), [In2(popha)2(4,4′-bipy)2]·3 H2O (InPF-19), [In(OH)(Hpopha)]·0.5 (1,7-phen) (InPF-20), and [In(popha)(1,10-phen)]·4 H2O (InPF-21) (InPF=indium polymeric framework, H3popha=5-(4-carboxy-2-nitrophenoxy)isophthalic acid, phen=phenanthroline, bipy=bipyridine), have been hydrothermally obtained by using both conventional heating (CH) and microwave (MW) procedures. These indium frameworks show efficient Lewis acid behavior for the solvent-free cyanosilylation of carbonyl compounds, the one pot Passerini 3-component (P-3CR) and the Ugi 4-component (U-4CR) reactions. In addition, InPF-17 was found to be a highly reactive, recyclable, and environmentally benign catalyst, which allows the efficient synthesis of α-aminoacyl amides. The relationship between the Lewis base/acid active site and the catalytic performance is explained by the 2D seven-coordinated indium framework of the catalyst InPF-17. This study is an attempt to highlight the main structural and synthetic factors that have to be taken into account when planning a new, effective MOF-based heterogeneous catalyst for multicomponent reactions.
- Aguirre-Díaz, Lina María,Iglesias, Marta,Snejko, Natalia,Gutiérrez-Puebla, Enrique,Monge, M. ángeles
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p. 6654 - 6665
(2016/05/09)
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- Preparation and synthesis method of chiral L-valine copper complex
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The invention relates to a chiral L-valine copper complex crystal of which the chemical formula is disclosed in the specification. The synthesis method of the chiral L-valine copper complex comprises the following steps: synthesis: weighing 1.7259g (0.015mol) of L-valine, putting the L-valine into a 100mL round-bottom flask, adding 40mL of absolute methanol, and dissolving by stirring; adding 0.9051g (0.05mol) of cupric chloride dihydrate into the solution, and heating under reflux for 48 hours; after the reaction finishes, filtering the reaction solution while the solution is hot, dissolving the filter residue in 20mL of absolute methanol and 20mL of distilled water, and carrying out natural volatilization for several days until a blue crystal precipitates; and flushing the blue crystal with petroleum ether and n-hexane three times, and carrying out vacuum drying for 30 minutes to obtain the target product. The chiral L-valine copper complex has favorable catalytic effects in the nitrile silicification reaction of benzaldehyde and the Henry reaction of ethyl pyruvate, and the conversion rates are respectively 82% and 90%.
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Paragraph 0010
(2016/12/22)
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- Synthesis, characterization, and reactivity of lanthanide amides incorporating neutral pyrrole ligand. Isolation and characterization of active catalyst for cyanosilylation of ketones
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A series of lanthanide amido complexes incorporating a neutral pyrrole ligand were synthesized and characterized, and their catalytic activities were studied. Treatment of [(Me3Si)2N]3Ln(μ-Cl)Li(THF)3 with 1 equ
- Wang, Fenhua,Wei, Yun,Wang, Shaowu,Zhu, Xiancui,Zhou, Shuangliu,Yang, Gaosheng,Gu, Xiaoxia,Zhang, Guangchao,Mu, Xiaolong
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- Mechanism-Based inactivation of human cytochrome p450 3A4 by two piperazine-Containing compounds
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Human cytochrome P450 3A4 (CYP3A4) is responsible for the metabolism of more than half of pharmaceutic drugs, and inactivation of CYP3A4 can lead to adverse drug-drug interactions. The substituted imidazole compounds 5-fluoro-2-[4-[(2-phenyl-1H-imidazol-5-yl) methyl]-1-piperazinyl]pyrimidine (SCH 66712) and 1-[(2-ethyl-4-methyl-1H-imidazol-5-yl)methyl]-4-[4-(trifluoromethyl)-2-pyridinyl]piperazine (EMTPP) have been previously identified as mechanism-based inactivators (MBI) of CYP2D6. The present study shows that both SCH 66712 and EMTPP are also MBIs of CYP3A4. Inhibition of CYP3A4 by SCH 66712 and EMTPP was determined to be con-centration, time, and NADPH dependent. In addition, inactivation of CYP3A4 by SCH 66712 was shown to be unaffected by the presence of electrophile scavengers. SCH 66712 displays type I binding to CYP3A4 with a spectral binding constant (Ks) of 42.9 ± 2.9 μM. The partition ratios for SCH 66712 and EMTPP were 11 and 94, respectively. Whole protein mass spectrum analysis revealed 1:1 binding stoichiometry of SCH 66712 and EMTPP to CYP3A4 and a mass increase consistent with adduction by the inactivators without addition of oxygen. Heme adduction was not apparent. Multiple monooxygenation products with each inactivator were observed; no other products were apparent. These are the first MBIs to be shown to be potent inactivators of both CYP2D6 and CYP3A4.
- Bolles, Amanda K.,Fujiwara, Rina,Briggs, Erran D.,Nomeir, Amin A.,Furge, Laura Lowe
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p. 1471 - 1475
(2014/12/11)
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- The application of spontaneous flocculation for the preparation of lanthanide-containing polyoxometalates intercalated layered double hydroxides: highly efficient heterogeneous catalysts for cyanosilylation
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The lanthanide-containing polyoxometalates (POMs) have been intercalated into layered double hydroxides (LDHs) successfully through the spontaneous flocculation method, resulting in the formation of new heterogeneous LDHs–POMs catalysts Mg3Al–L
- Jia, Yueqing,Song, Yu-Fei,Zhao, Shen
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p. 172 - 180
(2020/12/07)
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- Synthesis of metallasiloxanes of group 13-15 and their application in catalysis
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Herein we report on the synthesis, characterization and catalytic application of metallasiloxanes of group 13-15. Reactions of R(Me)Si(OH) 2 (R = N(SiMe3)-2,6-iPr2C6H 3) (A) with Bi(NEt2)3, Sb(NEt2) 3, Ge[N(SiMe3)2]2 and AlMe 3 afforded [R(Me)SiO2BiNEt2]2 (1), [R(Me)SiO2SbOSi(OH)(Me)R]2 (2), [R(Me)SiO 2]3(GeH)2 (3), and [R(Me)SiO 2AlMe(THF)]2 (4), respectively. Reactions of RSi(OH) 3 (B) with Bi(NEt2)3 and AlMe3 produced complexes (RSiO3Bi)4 (5) and (RSiO 3)2[AlMe(THF)]3 (6). Compounds 1-6 have been characterized by IR and NMR spectroscopy, single crystal X-ray structure and elemental analysis. Each of the compounds 1, 2 and 4 features an eight-membered ring of composition Si2O4Bi2, Si 2O4Sb2 and Si2O4Al 2, while 3 and 6 exhibit a bicyclic structure with the respective skeletons of Si3O6Ge2 and Si2O 6Al3. Compound 5 has a cubic core of Si4O 12Bi4. Compounds 1-6 exhibit very good catalytic activity in the addition reaction of trimethylsilyl cyanide (TMSCN) with benzaldehyde. Compound 5 was found to be the best catalyst and its activity was probed in the reactions of TMSCN with a number of aldehydes and ketones.
- Li, Yan,Wang, Jinjin,Wu, Yile,Zhu, Hongping,Samuel, Prinson P.,Roesky, Herbert W.
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supporting information
p. 13715 - 13722
(2013/09/23)
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- Indium metal-organic frameworks as catalysts in solvent-free cyanosilylation reaction
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Two new Indium MOFs with the bending multicarboxylate ligand H 2dpmda as a linker and different N-donor ancillary ligands were obtained; the two compounds are isoreticular with 2D-hcb uninodal 3-connected nets. Comparison of their activity in c
- Aguirre-Diaz, Lina Maria,Iglesias, Marta,Snejko, Natalia,Gutierrez-Puebla, Enrique,Monge, M. Angeles
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p. 9562 - 9571
(2013/11/19)
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- A highly negatively charged γ-Keggin germanodecatungstate efficient for Knoevenagel condensation
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A tetra-n-butylammonium (TBA) salt of a γ-Keggin -6-charged germanodecatungstate, [γ-H2GeW10O36] 6- (I), could act as an efficient homogeneous catalyst for Knoevenagel condensation of active methylene compounds with carbonyl compounds.
- Sugahara, Kosei,Kimura, Toshihiro,Kamata, Keigo,Yamaguchi, Kazuya,Mizuno, Noritaka
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p. 8422 - 8424
(2012/10/29)
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- Polystyrene-supported TBD as an efficient and reusable organocatalyst for cyanosilylation of aldehydes, ketones, and imines
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Polystyrene-supported TBD (PS-TBD) catalyzes cyanosilylation of both aldehydes and ketones using TMSCN to give the corresponding products in high yields. Imines were also converted into the desired α-cyanoanimes under the same conditions. PS-TBD was easil
- Matsukawa, Satoru,Fujikawa, Syohei
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supporting information; experimental part
p. 1075 - 1077
(2012/04/17)
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- Rasta resin-PPh3BnCl and its use in chromatography-free carbonyl cyanosilylation reactions
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Rasta resin-PPhnCl, a new heterogeneous polystyrene-based phosphonium salt, has been synthesized and used to catalyze cyanosilylation reactions of aldehydes and ketones. It was found to be more efficient as a catalyst than a similar heterogeneous phosphon
- Teng, Yan,Toy, Patrick H.
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supporting information; experimental part
p. 551 - 554
(2011/04/23)
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- Efficient, rapid and solvent-free cyanosilylation of aldehydes and ketones catalyzed by SbCl3
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Antimony trichloride(SbCl3) was demonstrated to be an effective catalyst for the cyanosilylation of a wide variety of carbonyl compounds under solvent-free conditions. The reactions proceeded smoothly at room temperature to afford the correspon
- Pourmousavi,Salahshornia
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experimental part
p. 1575 - 1578
(2011/12/15)
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- Mild and efficient trimethylsilylcyanation of ketones catalysed by PNP chloride
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Mild & green: The commercially and readily available PNPCl behaves as a very effective catalyst for the synthesis of various trimethylsilyl cyanohydrins from a wide range of aliphatic, cyclic, α,β-unsaturated and aromatic ketones. The method proceeds at r
- Lacour, Marie-Agnes,Rahier, Nicolas J.,Taillefer, Marc
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supporting information; experimental part
p. 12276 - 12279
(2011/12/15)
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- GSK-3BETA INHIBITOR
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For the purpose of providing a GSK-3β inhibitor containing a 2-aminopyridine compound or a salt thereof or a prodrug thereof useful as an agent for the prophylaxis or treatment of a GSK-3β-related pathology or disease, the present invention provides a GSK-3β inhibitor containing a compound represented by the formula (IA): wherein each symbol is as defined in the specification. or a salt thereof or a prodrug thereof.
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Page/Page column 31
(2011/04/13)
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- Highly efficient cyanosilylation of sterically bulky ketones catalyzed by tin ion-exchanged montmorillonite
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Tin ion-exchanged montmorillonite (SnMont) was found to be a powerful catalyst for the cyanosilylation of aromatic and aliphatic ketones having a carbonyl group in sterically congested circumstances with cyanotrimethylsilane, giving the corresponding cyan
- Wang, Jiacheng,Masui, Yoichi,Watanabe, Kenya,Onaka, Makoto
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supporting information; experimental part
p. 553 - 557
(2009/10/25)
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- A Tin-tungsten mixed oxide as an efficient heterogeneous catalyst for C-C Bond Bond-Forming reactions
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The tin-tungsten mixed oxide prepared by the calcination of the tin-tungsten hydroxide precursor with a Sn/W molar ratio of 2 at 800 °C (SnW2-800) acts as an effective and reusable solid catalyst for C-C bond-forming reactions, such as the cyclization of citronellal, the Diels-Alder reaction, and the cyanosilylation of carbonyl compounds with trimethylsilyl cyanide (TMSCN). Various kinds of structurally diverse aliphatic, aromatic, and unsaturated, heteroatom-containing substrates could be converted into the desired products in high to excellent yields. The observed catalyses for these reactions were truly heterogeneous and the recovered catalyst could be reused several times without an appreciable loss of its high catalytic performance. The Bronsted acid sites generated on the aggregated polytungstate species on SnW2-800 likely play an important role in the C-C bond-forming reactions.
- Ogasawara, Yoshiyuki,Uchida, Sayaka,Yamaguchi, Kazuya,Mizuno, Noritaka
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experimental part
p. 4343 - 4349
(2009/11/30)
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- Alkali salt of L-proline as an efficient and practical catalyst for the cyanosilylation of a wide variety of carbonyl compounds under solvent-free conditions
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The alkali salt of L-proline was demonstrated to be an efficient and practical catalyst for the cyanosilylation of a wide variety of simple and functionalized carbonyl compounds under solvent-free conditions. The reactions proceeded smoothly at room temperature to afford the corresponding cyanohydrins in good to excellent yields. Copyright Taylor & Francis Group, LLC.
- Shen, Zhi-Liang,Ji, Shun-Jun
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experimental part
p. 775 - 791
(2009/08/08)
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- Activation of trimethylsilyl cyanide by potassium phthalimide for facile synthesis of TMS-protected cyanohydrins
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Potassium phthalimide was found to be a highly effective and easily accessible organocatalyst for the cyanosilylation of various carbonyl compounds under extremely mild conditions. The corresponding cyanohydrin trimethylsilyl ethers were obtained in high
- Dekamin, Mohammad G.,Karimi, Zahra
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experimental part
p. 1789 - 1794
(2009/08/14)
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- An expeditious synthesis of cyanohydrin trimethylsilyl ethers using tetraethylammonium 2-(carbamoyl)benzoate as a bifunctional organocatalyst
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Phthalimide and tetraethylammonium hydroxide react via an unusual pathway to afford tetraethylammonium 2-(carbamoyl)benzoate (TEACB) which is of interest as a bifunctional organocatalyst. TEACB (0.5 mol %) was found to catalyze the addition of trimethylsi
- Dekamin, Mohammad G.,Sagheb-Asl, Solmaz,Reza Naimi-Jamal
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scheme or table
p. 4063 - 4066
(2009/10/11)
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- A new scandium metal organic framework built up from octadecasil zeolitic cages as heterogeneous catalyst
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Zeolitic cages of the AST type are found in the novel scandium-squarate MOF, and the joining of them gives rise to a new binodal network with a unique topology; this new material is an efficient heterogeneous Lewis acid catalyst. The Royal Society of Chemistry 2009.
- Gandara, Felipe,Gomez-Lor, Berta,Iglesias, Marta,Snejko, Natalia,Gutierrez-Puebla, Enrique,Monge, Angeles
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supporting information; experimental part
p. 2393 - 2395
(2009/09/06)
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- Remarkable acceleration of cyanosilylation by the mesoporous Al-MCM-41 catalyst
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The presence of the heterogeneous mesoporous Al-MCM-41 catalyst remarkably accelerated the cyanosilylation of various aldehydes and ketones with trialkylsilyl cyanide, giving the corresponding cyanohydrin silyl ethers in quantitative yields under mild reaction conditions. The Royal Society of Chemistry.
- Iwanami, Katsuyuki,Choi, Jun-Chul,Lu, Baowang,Sakakura, Toshiyasu,Yasuda, Hiroyuki
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p. 1002 - 1004
(2008/09/21)
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- Gold(III)-catalyzed cyanosilylation of ketones and aldehydes
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Gold(III) chloride was found to be a highly efficient catalyst for the cyanosilylation of various ketones and aldehydes. The reactions were complete within 30 minutes at room temperature in the presence of only one mol% gold(III) chloride, yielding the co
- Woo, Kyung Cho,Sung, Min Kang,Medda, Amiya K.,Lee, Jungkyu K.,Choi, Insung S.,Lee, Hee-Seung
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p. 507 - 510
(2008/12/21)
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- Chiral lithium salts of phosphoric acids as Lewis acid-base conjugate catalysts for the enantioselective cyanosilylation of ketones
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The catalytic enantioselective cyanosilylation of aromatic ketones was developed by using chiral lithium salts of (R)-BINOL- or (S)-BINAM-derived phosphoric acid compounds. In the presence of 10 mol% of chiral conjugate lithium salts, the corresponding tertiary cyanohydrins were obtained in high yields with moderate to high enantio-selectivities. This is the first efficient example of asymmetric catalysis using lithium salts of synthetically useful chiral phosphoric acid compounds. A possible catalytic mechanism and transition states are also discussed as a preliminary working hypothesis.
- Hatano, Manabu,Ikeno, Takumi,Matsumura, Tokihiko,Torii, Shinobu,Ishihara, Kazuaki
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supporting information; experimental part
p. 1776 - 1780
(2009/07/01)
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- Size-selective Lewis acid catalysis in a microporous metal-organic framework with exposed Mn2+ coordination sites
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Treatment of selected aldehydes and ketones with cyanotrimethylsilane in the presence of the microporous metal-organic framework Mn3[(Mn4Cl)3BTT8(CH3OH)10]2 (1, H3BTT = 1,3,5-ben
- Horike, Satoshi,Dinca, Mircea,Tamaki, Kentaro,Long, Jeffrey R.
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p. 5854 - 5855
(2008/09/20)
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- Cyanosilylation of aldehydes and ketones catalyzed by nanocrystalline magnesium oxide
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Cyanosilylation of various aldehydes and ketones with TMSCN proceeded smoothly under mild conditions to give the corresponding cyanohydrin trimethylsilyl ethers in the presence of nanocrystalline magnesium oxide. The cyanohydrin trimethylsilyl ethers of aldehydes produced cyanohydrins in good to high yields on treatment with 2 N HCl. 29Si NMR spectral evidence proved that the reaction proceeds through the hypervalent silicate species by coordination to O2-/O- (Lewis basic site) of nanocrystalline magnesium oxide. Copyright Taylor & Francis Group, LLC.
- Lakshmi Kantam,Mahendar, Koosam,Sreedhar, Bojja,Vijay Kumar,Choudary
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experimental part
p. 3919 - 3936
(2009/04/11)
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- Rhodium-catalyzed silylation and intramolecular arylation of nitriles via the silicon-assisted cleavage of carbon-cyano bonds
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A rhodium-catalyzed silylation reaction of carbon - cyano bonds using disilane has been developed. Under these catalytic conditions, carbon-cyano bonds in aryl, alkenyl, allyl, and benzyl cyanides bearing a variety of functional groups can be silylated. The observation of an enamine side product in the silylation of benzyl cyanides and related stoichiometric studies indicate that the carbon-cyano bond cleavage proceeds through the deinsertion of silyl isocyanide from η2-iminoacyl complex B. Knowledge gained from these studies has led to the development of a new intramolecular biaryl coupling reaction in which aryl cyanides and aryl chlorides are cross-coupled.
- Tobisu, Mamoru,Kita, Yusuke,Ano, Yusuke,Chatani, Naoto
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supporting information; experimental part
p. 15982 - 15989
(2009/05/16)
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- Rhodium(III) iodide hydrate catalyzed three-component coupling reaction: synthesis of α-aminonitriles from aldehydes, amines, and trimethylsilyl cyanide
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Aryl imines formed from aldehydes and amines undergo smoothly in situ nucleophilic addition with trimethylsilyl cyanide (TMSCN) in the presence of catalytic amount of hydrated rhodium(III) iodide to?afford the corresponding α-aminonitriles in excellent yield. The low catalytic loading (2 mol %), mild experimental conditions, and short reaction time (mostly within 13 min) represent the key features of this novel catalytic system.
- Majhi, Anjoy,Kim, Sung Soo,Kadam, Santosh T.
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p. 5509 - 5514
(2008/12/20)
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- Robust and efficient, yet uncatalyzed, synthesis of trialkylsilyl-protected cyanohydrins from ketones
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(Chemical Equation Presented) High-yielding cyanosilylation of ketones with NaCN and various chlorotrialkylsilanes in DMSO proceeds smoothly without catalysis to give silyl-protected ketone cyanohydrins. The unique role of DMSO consists in rendering naked
- Cabirol, Fabien L.,Lim, Angela E. C.,Hanefeld, Ulf,Sheldon, Roger A.,Lyapkalo, Ilya M.
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p. 2446 - 2449
(2008/09/19)
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