- Trimethylsilyl cyanide addition to carbonyl compounds under neutral condition catalyzed by iodine
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Reaction of trimethylsilyl cyanide with aliphatic or aromatic aldehydes and ketones in the presence of a catalytic amount of elemental iodine produced the corresponding cyanohydrin trimethylsilyl ethers in very short time and high yields.
- Azizi, Najmedin,Saidi, Mohammad R.
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Read Online
- Pickering emulsion droplets hosting ionic liquid catalysts for continuous-flow cyanosilylation reaction
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An IL-catalyzed cyanosilylation reaction is an important route for synthesis of many fine chemicals, but it is currently conducted in a batch manner. Herein, we have developed a novel method to "immobilize" IL catalysts for continuous-flow reaction based
- Meng, Zhixin,Zhang, Ming,Yang, Hengquan
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Read Online
- Solvent-free heterogeneous catalysis for cyanosilylation in a modified sodalite-type Cu(II)-MOF
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Solvothermal reaction of Cu(OAc)2 and H3BTT·2HCl generated a sodalite-type metal-organic framework [(Cu4O0.27Cl0.73)3(H0.5BTT)8(H2O)12]·3MeOH·9DM
- Zhang, Ling-Juan,Han, Cai-Yun,Dang, Qin-Qin,Wang, Yan-Hong,Zhang, Xian-Ming
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Read Online
- Controllable Synthesis and Catalytic Performance of Nanocrystals of Rare-Earth-Polyoxometalates
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Large-scale isolation of nanocrystals of rare-earth-polyoxometalates (RE-POMs) catalysts is important in fundamental research and applications. Here, we synthesized a family of monomeric RE-POMs by the self-assembly of Ta/W mixed-addendum POM {P2/su
- Li, Shujun,Zhou, Yanfang,Peng, Qingpo,Wang, Ruoya,Feng, Xiaoge,Liu, Shuxia,Ma, Xiaoming,Ma, Nana,Zhang, Jie,Chang, Yi,Zheng, Zhiping,Chen, Xuenian
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Read Online
- Determination, par spectrometries infrarouge et Raman, de la stereochimie de cyclohexylcyanhydrines O-trimethylsilylees
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A homogeneous series of α-trimethylsiloxynitriles 1-8, obtained by cyanosilylation of cyclohexanones, was investigated by Raman and IR spectroscopies.This study yielded information that complements previous fragmentary NMR results.It was shown that both p
- Marchand, Annette,Gerval, Pierre,Picard, Jean-Paul
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Read Online
- Niobium phytate prepared from phytic acid and NbCl5: A highly efficient and heterogeneous acid catalyst
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The preparation of functional catalysts using naturally-occurring building blocks is of great importance. In this work, we designed a functional heterogeneous acid catalyst, niobium phytate, using phytic acid, which could be obtained from the seeds and grains of plants, as the building block to react with NbCl5. The prepared niobium phytate was characterized by XRD, FT-IR, XPS, SEM, TEM, NH3-TPD and N2 adsorption-desorption examinations. Niobium phytate showed very high activity for both cyanosilylation of carbonyl compounds and dehydration of carbohydrates. It was also found that niobium phytate had higher activity than commercial Nb2O5. In addition, niobium phytate could be easily recovered and reused without reducing the reaction activity considerably. Further study indicated that both higher acidity and lower crystallinity contributed significantly to the excellent catalytic performance of niobium phytate. The findings in this work provide insights into the design of new functional catalysts using naturally-occurring building blocks for various organic reactions.
- Xue, Zhimin,Zhang, Yuwei,Li, Guofeng,Wang, Jinfang,Zhao, Wancheng,Mu, Tiancheng
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Read Online
- A micro-environment tuning approach for enhancing the catalytic capabilities of lanthanide containing polyoxometalate in the cyanosilylation of ketones
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The as-synthesized (TBA)8H5[Nd(SiW11O39)2] manifested high catalytic activity for cyanosilylation of ketones, and its catalytic activity could be improved further through rational design of the reacti
- Li, Sang-Hao,Lin, Ming-Yuan,Nie, Yan-Mei,Yan, Jun
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Read Online
- Supported ionic liquid-like phases as organocatalysts for the solvent-free cyanosilylation of carbonyl compounds: From batch to continuous flow process
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Supported ionic liquid-like phases (SILLPs) are able to efficiently catalyse the cyanosilylation of carbonyl compounds using trimethylsilyl cyanide under solvent-free conditions. These organic catalysts were efficient for various carbonyl compounds includ
- Martin, Sergio,Porcar, Raul,Peris, Edgar,Burguete, Maria Isabel,Garcia-Verdugo, Eduardo,Luis, Santiago V.
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Read Online
- Synthesis, characterization, crystal structure of magnesium compound based 3, 3′, 5, 5′-azobenzentetracarboxylic acid and application as high-performance heterogeneous catalyst for cyanosilylation
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A novel coordination compound with the formula {[H3O]2[Mg(ABTC)(DMI)2]}n (1) (H4ABTC?=?3,3′,5,5′-azobenzene-tetracarboxylic acid, DMI?=?1,3-dimethy-2-imidazolidinone) as synthesized under solvothermal
- Li, Yong-Peng,Zhang, Ling-Juan,Ji, Wen-Juan
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Read Online
- 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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supporting information
p. 16035 - 16044
(2021/09/02)
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- n-Butyllithium as a highly efficient precatalyst for cyanosilylation of aldehydes and ketones
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A highly efficient cyanosilylation protocol mediated by the easily availablen-BuLi with a wide range of aldehydes and ketones was developed. This protocol features excellent yields with very lown-BuLi loadings (0.01-0.05 mol%) at room temperature, solvent
- Kang, Zihan,Wang, Yuhong,Xu, Xiaojuan,Xue, Mingqiang,Zhang, Wenxuan,Zhou, Shuai,Zhu, Xu
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supporting information
p. 7432 - 7437
(2021/09/07)
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- A novel yttrium-based metal-organic framework for the efficient solvent-free catalytic synthesis of cyanohydrin silyl ethers
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A new porous metal-organic framework (MOF) with the chemical formula [Y5L6(OH)3(DMF)3]·5H2O (1) (where L = 3-amino-4-hydroxybenzoate) has been prepared by a solvothermal procedure. The structural char
- Cepeda, Javier,Echenique-Errandonea, Estitxu,Fernández, Ignacio,Pérez, Juana M.,Rodríguez-Diéguez, Antonio,Rojas, Sara,Seco, José M.
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supporting information
p. 11720 - 11724
(2021/09/06)
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- Synthesis of cyanooxovanadate and cyanosilylation of ketones
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The cyanosilylation was performed by using metavanadate catalysts, and in situ measurements revealed the formation of [VO2(CN)3]2- and [VO4TMS2]- under reaction conditions. The reaction of [VO2(CN)3]2-, trimethylsilyl cyanide (TMSCN), and water afforded [
- Hayashi, Yoshihito,Kawabata, Hiroko,Kikukawa, Yuji
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p. 31688 - 31692
(2021/11/30)
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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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- 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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- Application of n-butyllithium in catalyzing cyanosilylation reaction of ketone and silane
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The invention discloses an application of n-butyllithium in catalyzing cyanosilylation reaction of ketone and silane. The n-butyllithium has high catalytic activity, low catalyst dosage and good substrate application range. After n-butyllithium, ketone an
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Paragraph 0028-0029
(2020/07/13)
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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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- 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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supporting information
p. 3042 - 3044
(2018/03/28)
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- Exploring physical and chemical properties in new multifunctional indium-, bismuth-, and zinc-based 1D and 2D coordination polymers
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Main group element coordination polymers (MGE-CPs) are important compounds for the development of multifunctional materials. However, there has been a shortage of studies regarding their structural, optical, catalytic, mechanical, and antibacterial proper
- Gomez,D'Vries,Lionello,Aguirre-Díaz,Spinosa,Costa,Fuertes,Pizarro,Kaczmarek,Ellena,Rozes,Iglesias,Van Deun,Sanchez,Monge,Soler-Illia
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p. 1808 - 1818
(2018/02/17)
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- Catalytic cyanosilylation using germylene stabilized platinum(ii) dicyanide
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The ability of a platinum compound to act as a catalyst for the cyanosilylation of carbonyl compounds is demonstrated through a well-defined germylene stabilized Pt(ii) dicyanide, trans-{(iBu)2ATIGe(iPr)}2Pt(CN)
- Sharma, Mahendra Kumar,Singh, Dharmendra,Mahawar, Pritam,Yadav, Ravi,Nagendran, Selvarajan
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supporting information
p. 5943 - 5947
(2018/05/14)
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- Synthesis of magnetically recoverable imidazolium hydrogen carbonate and its application as an N-heterocyclic carbene catalyst to cyanosilylation of aldehydes and ketones
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We prepared a magnetically recoverable imidazolium hydrogen carbonate by immobilizing an imidazolium hydrogen carbonate on magnetite and applied it as an N-heterocyclic carbene catalyst to the cyanosilylation of aldehydes and ketones. By employing the magnetite-supported imidazolium hydrogen carbonate as a catalyst, the cyanosilylation proceeded at 60?°C to provide the corresponding trimethylsilylated cyanohydrin in a fair chemical yield. Moreover, after the reaction, the magnetic catalyst was readily recovered by use of an external magnet and could be reused up to five times.
- Fujii, Akira,Choi, Jun-Chul,Fujita, Ken-ichi
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supporting information
p. 1515 - 1518
(2017/03/24)
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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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- 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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p. 439 - 444
(2017/02/24)
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- GLYCINE TRANSPORTER INHIBITOR
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The present invention provides novel compounds of formula [IA] or pharmaceutically acceptable salts thereof: which are useful in the prevention or treatment of diseases such as schizophrenia, Alzheimer's disease, cognitive impairment, dementia, anxiety disorders (e.g., generalized anxiety disorder, panic disorder, obsessive-compulsive disorder, social anxiety disorder, post-traumatic stress disorder, specific phobias, acute stress disorder), depression, drug dependence, spasm, tremor, pain, Parkinson's disease, attention deficit hyperactivity disorder, bipolar disorder, eating disorder, or sleep disorders, which is based on the glycine uptake-inhibiting action.
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Paragraph 0569; 0573; 0577
(2016/06/06)
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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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p. 1947 - 1952
(2016/11/25)
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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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- Toward understanding the structure-catalyst activity relationship of new indium MOFs as catalysts for solvent-free ketone cyanosilylation
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Four new indium metal-organic frameworks, MOFs, namely [In2(hfipbb)3(1,10-phen)2]·2H2O (InPF-12), [In2(hfipbb)3(2,2′-bipy)2]·2H2O (InPF-13), [In2(hfipbb)su
- Aguirre-Daz, Lina Mara,Iglesias, Marta,Snejko, Natalia,Gutirrez-Puebla, Enrique,Monge, M. ngeles
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p. 7058 - 7065
(2015/01/30)
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- Porous Zirconium-Phytic Acid Hybrid: A Highly Efficient Catalyst for Meerwein-Ponndorf-Verley Reductions
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The utilization of compounds from natural sources to prepare functional materials is of great importance. Herein, we describe for the first time the preparation of organic-inorganic hybrid catalysts by using natural phytic acid as building block. Zirconium phosphonate (Zr-PhyA) was synthesized by reaction of phytic acid and ZrCl4 and was obtained as a mesoporous material with pore sizes centered around 8.5 nm. Zr-PhyA was used to catalyze the mild and selective Meerwein-Ponndorf-Verley (MPV) reduction of various carbonyl compounds, e.g., of levulinic acid and its esters into γ-valerolactone. Further studies indicated that both Zr and phosphate groups contribute significantly to the excellent performance of Zr-PhyA. All natural: Porous zirconium phosphonate (Zr-PhyA) was synthesized simply by reaction of natural phytic acid (PhyA) and ZrCl4 and applied as a very efficient catalyst for the Meerwein-Ponndorf-Verley reduction of various carbonyl compounds. Both the Zr element and phosphate groups contributed significantly to the excellent catalytic performance of Zr-PhyA.
- Song, Jinliang,Zhou, Baowen,Zhou, Huacong,Wu, Lingqiao,Meng, Qinglei,Liu, Zhimin,Han, Buxing
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supporting information
p. 9399 - 9403
(2015/08/06)
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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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- Tri-lacunary polyoxometalates of Na8H[PW9O 34] as heterogeneous Lewis base catalysts for Knoevenagel condensation, cyanosilylation and the synthesis of benzoxazole derivatives
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We reported for the first time the development of tri-lacunary polyoxometalates (POMs) of Na8H[A-PW9O34] ·7H2O and Na8H[B-PW9O 34]·19H2O (Na-A-PW9 and Na-B-PW 9) as highly selective and efficient heterogeneous Lewis base catalysts for Knoevenagel condensation, cyanosilylation of various aldehydes and ketones and the synthesis of benzoxazole derivatives at 25 C under mild conditions. Since both Na-A-PW9 and Na-B-PW9 display no characteristic porosity, it is proposed that the catalytic reactions proceed not only on the surface and interface, but also in the bulk phase. The catalysts can be easily recovered and reused for at least six times without obvious decrease of catalytic activities and the structures of the catalysts remain unchanged after recycling. The easy preparation, high efficiency, reusability of the heterogeneous catalysts of Na-A-PW9 and Na-B-PW9 exhibit great potential for further application.
- Zhao, Shen,Chen, Yang,Song, Yu-Fei
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p. 140 - 146
(2014/03/21)
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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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- 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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- Method for the efficient synthesis of highly-substituted oxetan- and azetidin-, dihydrofuran- and pyrrolidin-3-ones and its application to the synthesis of (±)-pseudodeflectusin
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Highly substituted four- and five-membered heterocycles were prepared starting with O,P- and N,P-acetals by using a one-pot method involving base induced cyclization and a Horner-Wadsworth-Emmons (HWE) olefination reaction. Divergent synthesis of various heterocycles was achieved by using this method and transformations of the alkenyl group in the products of these processes were exemplified. Finally, a short and efficient synthesis of (±)- pseudodeflectusin based on the new methodology was achieved.
- Maegawa, Tomohiro,Otake, Kazuki,Hirosawa, Keiichi,Goto, Akihiro,Fujioka, Hiromichi
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supporting information
p. 4798 - 4801
(2013/01/15)
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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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- 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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- 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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- Benign coupling of reactions and separations with reversible ionic liquids
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Reversible ionic liquids are a novel class of solvents that combine an effective medium where reactions occur with a 'built-in' separation ability for facile recovery of the products and catalysts, making the solvent available for recycle. We report the utility of these solvents in a number of reactions (Claisen-Schmidt condensation, Heck C-C coupling, and CO2 capture) and discuss the effectiveness of the separation. We also provide insight into the challenges and limitations of using these unique solvent systems to couple reactions and separations.
- Hart, Ryan,Pollet, Pamela,Hahne, Dominique J.,John, Ejae,Llopis-Mestre, Veronica,Blasucci, Vittoria,Huttenhower, Hillary,Leitner, Walter,Eckert, Charles A.,Liotta, Charles L.
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experimental part
p. 1082 - 1090
(2010/03/30)
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- Organocatalytic synthesis of cyanohydrin trimethylsilyl ethers by potassium 4-benzylpiperidinedithiocarbamate under solvent-free conditions
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Potassium 4-benzylpiperidinedithiocarbamate was found to be an efficient organocatalyst for facile addition of trimethylsilyl cyanide to a wide variety of aldehydes and ketones to afford corresponding cyanohydrin trimethylsilyl ethers in high to quantitat
- Dekamin, Mohammad G.,Alizadeh, Roghieh,Naimi-Jamal, M. Reza
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experimental part
p. 229 - 235
(2010/11/17)
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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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experimental part
p. 946 - 948
(2010/04/23)
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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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experimental part
p. 3353 - 3359
(2009/12/26)
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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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- BENZISOXAZOLE COMPOUND
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Disclosed is a compound represented by the general formula (I) or a salt thereof: wherein any one of R1, R2 and R3 represents a group represented by the formula: -(CH2)m-NR11R12 (wherein m is 1 or 2; and R11 and R12 independently represent a hydrogen atom or a C1-6 alkyl group or may, together with a nitrogen atom to which R11 and R12 are bound, form a 4- or 5-membered cyclic group); the remaining two or R1, R2 and R3 independently represent a group represented by the formula: -(O)n-R21 (wherein n is 0 or 1; and R21 represents a hydrogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, or the like); and R4 represents a C1-6 alkyl group which may have a substituent or the like.
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Page/Page column 91
(2009/02/10)
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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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- 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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- 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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- Fe(Cp)2PF6: An efficient catalyst for cyanosilylation of carbonyl compounds under solvent free condition
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An efficient method for the addition of trimethylsilyl cyanide (TMSCN) to various aldehydes and ketones has been described using Fe(Cp)2PF6 (2.5 mol%) as a catalyst under solvent free condition. Excellent yields of trimethylsilylethe
- Khan, Noor-ul H.,Agrawal, Santosh,Kureshy, Rukhsana I.,Abdi, Sayed H.R.,Singh, Surendra,Jasra, Raksh V.
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p. 4361 - 4366
(2008/02/13)
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- Neutral π-nucleophile-catalyzed cyanation of aldehydes and ketones
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1-Methoxy-2-methyl-1-(trimethylsiloxy)propene, a neutral π-nucleophile, was found to be able to efficiently catalyze the cyanation (cyanosilylation and cyanocarbonation) of various aldehydes and ketones, and this study provided the first illustration of u
- Wang, Xiu,Tian, Shi-Kai
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p. 1416 - 1420
(2008/03/11)
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- Catalytic cyanosilylation of ketones with simple phosphonium salt
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In the presence of 1-5 mol % of benzyltriphenylphosphonium chloride, a wide variety of unconjugated and conjugated, acyclic and cyclic ketones were transformed to their corresponding cyanohydrin silyl ethers in excellent yields.
- Wang, Xiu,Tian, Shi-Kai
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p. 6010 - 6013
(2008/02/10)
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- DMAP-organocatalyzed O-silyl-O-(or C-)-benzoyl interconversions by means of benzoyl fluoride
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A mild and efficient transprotection of alcohols from silyl ethers 1a-f to benzoates 2a-f is reported in fair to good yields (50-98%). This silyl-acyl exchange reaction proceeds readily in acetonitrile at room temperature in the presence of benzoyl fluoride and DMAP as an acyl transfer catalyst. A two-step 'one-pot' DMAP-catalyzed silylcyanation-transprotection sequence which gives the corresponding O-benzoyl cyanohydrines 2g-l in high yields (72-98%) from various benzaldehyde and ketone derivatives is also reported. This original organocatalytic acyl transfer process was also found to be effective in the O-benzoylation of trimethysilyl enolates 1m-o, providing enol esters 2m-o. Lastly, the potential of this strategy is also illustrated by a DMAP-mediated Claisen condensation between ketene silyl acetals 1p-r and benzoyl fluoride. Georg Thieme Verlag Stuttgart.
- Poisson, Thomas,Dalla, Vincent,Papamica?l, Cyril,Dupas, Georges,Marsais, Francis,Levacher, Vincent
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p. 381 - 386
(2008/01/08)
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- Highly efficient trialkylsilylcyanation of aldehydes, ketones and imines catalyzed by a nucleophilic N-heterocyclic carbene
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The synthetic utility of N-heterocyclic carbenes was demonstrated by the trialkylsilylcyanation of aldehydes, ketones and imines. In the presence of a catalytic amount of 3a, the reactions with Me3SiCN proceeded smoothly to give the corresponding cyanohydrin trimethylsilyl ethers or amino nitrile derivatives in good to excellent yields.
- Kano, Taichi,Sasaki, Kouji,Konishi, Teppei,Mii, Haruka,Maruoka, Keiji
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p. 4615 - 4618
(2007/10/03)
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- Preparation, characterization and catalytic properties of polyaniline-supported metal complexes
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Polyaniline-supported Sc, In, Pd, Os and Re catalysts were prepared by using a simple protocol and the thus prepared catalysts were well characterized using FTIR, XPS, UV-Vis/DRS, TGA-DTA. All the catalysts were successfully employed in a wide range of organic transformations such as cyanation and allylation of carbonyl compound, Suzuki coupling of aryl halides and boronic acids, and, most importantly, in asymmetric dihydroxylation of olefins to afford optically active vicinal diols. All the catalysts were separated from the reaction mixture by simple filtration and reused with consistent activity for five cycles without noticeable leaching of metal from the support.
- Choudary, Boyapati M.,Roy, Moumita,Roy, Sarabindu,Kantam, M. Lakshmi,Sreedhar, Bojja,Kumar, Karasala Vijay
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p. 1734 - 1742
(2007/10/03)
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