- The catalytic activity of Zn(II) and Mn(II) organometallic complexes
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Zn(II) and Mn(II) organometallic complexes I and II were first used to catalyze the cyanosilylation reaction, and good catalytic results (24-99 %) were achieved. The catalytic activity of the complexes was determined by 1H NMR.
- Mei, Luo,Yan, Li Xiao,Wei, Chen,Hai, Zhang Jia
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Read Online
- Cyanosilylation of carbonyl compounds catalyzed by half-sandwich (η6-p-cymene) Ruthenium(II) complexes bearing heterocyclic hydrazone derivatives
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A new class of half-sandwich (?6-p-cymene) ruthenium(II) complexes supported by heterocyclic hydrazone derivatives of general formula [Ru(?6-p-cymene)(Cl)(L)] where L represents N’-((1H-pyrrol-2-yl)methylene)furan-2-carbohydrazide (L
- Alves, Luis G.,Bharathi, Madheswaran,Indira, Sekar,Martins, Ana M.,Shanmuga Bharathi, Kuppannan,Vinoth, Govindasamy
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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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supporting information
p. 16035 - 16044
(2021/09/02)
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- Silyl Cyanopalladate-Catalyzed Friedel-Crafts-Type Cyclization Affording 3-Aryloxindole Derivatives
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3-Aryloxindole derivatives were synthesized through a Friedel-Crafts-type cyclization. The reaction was catalyzed by a trimethylsilyl tricyanopalladate complex generated in situ from trimethylsilyl cyanide and Pd(OAc) 2. Wide varieties of diethyl phosphates derived from N -arylmandelamides were converted almost quantitatively into oxindoles. When N, N -dibenzylamide was used instead of an anilide substrate, a benzo-fused δ-lactam was obtained. An oxindole product was subjected to substitution reactions to afford 3,3-diaryloxindoles with two different aryl groups.
- Ece, Hamdiye,Tange, Yuji,Yurino, Taiga,Ohkuma, Takeshi
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supporting information
p. 935 - 939
(2021/02/22)
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- An uncoordinated tertiary nitrogen based tricarboxylate calcium network with Lewis acid-base dual catalytic sites for cyanosilylation of aldehydes
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The design and utilization of dual sites for synergistic catalysts has been recognised as an efficient method towards high-efficiency catalysis in the cyanosilylation of aldehydes, which gives key intermediates for the synthesis of a number of valuable na
- Wang, Ying-Xia,Wang, Hui-Min,Meng, Pan,Song, Dong-Xia,Hou, Juan-Juan,Zhang, Xian-Ming
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p. 1740 - 1745
(2021/02/16)
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- Organo-catalyzed Michael addition of 2-fluoro-2-arylacetonitriles
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An efficient synthesis of a variety of 2-arylacetonitriles containing a fluorinated stereogenic center through organo-catalyzed Michael addition reaction of 2-fluoro-2-arylacetonitriles has been developed. This protocol uses a cheap organocatalyst (DBU) and has a broad substrate scope: α, β-unsaturated ketones, esters, nitriles and sulfones were all successfully reacted. Importantly, water proved to be a good solvent for this reaction.
- Chen, De-Yin,Song, Shuai,Chen, Ling-Yan,Ren, Xinfeng,Li, Ya
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supporting information
(2021/03/01)
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- Conjugated Bis-Guanidines (CBGs) as β-Diketimine Analogues: Synthesis, Characterization of CBGs/Their Lithium Salts and CBG Li Catalyzed Addition of B?H and TMSCN to Carbonyls
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Herein, we report a range of conjugated bis-guanidines (CBGs) L [L={(ArHN)(ArHN)C=N?C=(NAr)(NHAr)}; Ar=2, 6-Me2 - C6H3, (1), 2, 4, 6-Me3?C6H2, (2), 2, 6-Et2?C6H3
- Peddarao, Thota,Baishya, Ashim,Sarkar, Nabin,Acharya, Rudresh,Nembenna, Sharanappa
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p. 2034 - 2046
(2021/05/27)
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- Pyrene carboxylate ligand based coordination polymers for microwave-assisted solvent-free cyanosilylation of aldehydes
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The new coordination polymers (CPs) [Zn(μ-1κO1:1κO2-L)(H2O)2]n·n(H2O) (1) and [Cd(μ4-1κO1O2:2κN:3,4κO3-L)(H2O)]n·n(H2
- Da Silva, M. Fátima C. Guedes,Karmakar, Anirban,Paul, Anup,Pombeiro, Armando J. L.,Sabatini, Elia Pantanetti
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- Alkoxo bridged heterobimetallic CoIIISnIV compounds with face shared coordination octahedra: Synthesis, crystal structure and cyanosilylation catalysis
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The self-assembly reaction of the Schiff base N,N’-ethylenebis(2-hydroxyacetophenoneimine) (H2L), CoCl2··6H2O and [SnPh2Cl2] led to the alkoxo-bridged heteroorganometallic CoIIISnIV/s
- Hazra, Susanta,Karmakar, Anirban,Pombeiro, Armando J. L.,da Silva, M. Fátima C. Guedes
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supporting information
(2021/07/13)
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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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- Zirconium-based MOF catalyst with double active sites and preparation method and application thereof
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The invention discloses a zirconium-based MOF catalyst loaded with double active sites as well as a preparation method and an application of the zirconium-based MOF catalyst. The method comprises thefollowing steps: adding zirconium salt and an organic ligand into an organic solvent, taking organic acid as a regulator, and carrying out self-assembly reaction to obtain a metal organic framework; adding salicylaldehyde for aldehyde amine condensation to obtain chelating coordination sites, adding palladium salt, and performing coordination through an impregnation method; reducing the obtained MOF in hydrogen to obtain an MOF loaded with Pd nanoparticles; reacting MOF and zinc salt in an organic solvent, and obtaining the catalyst. The Pd-Zn-coated UiO-68-NH2-CH3 catalyst synthesized by thepreparation method disclosed by the invention has efficient catalytic activity in a tandem alcohol oxidation/aldehyde cyanosilylation reaction. According to the catalyst, a metal organic framework UiO-68-NH2-CH3 is constructed, Pd nanoparticles and Zn are loaded by taking the metal organic framework UiO-68-NH2-CH3 as a carrier, the loading capacity of the Pd nanoparticles is 4-8wt%, and the loading capacity of the Zn is 3-5wt%.
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Paragraph 0071; 0073; 0075-0079
(2021/06/09)
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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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- 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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- Role of aromatic: Vs. aliphatic amine for the variation of structural, electrical and catalytic behaviors in a series of silver phosphonate extended hybrid solids
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Four inorganic-organic hybrid silver phosphonate compounds, [Ag(C10H8N2)(H4hedp)] (1), [Ag2(C10H8N2)(H3hedp)]·2H2O (2), [C4H12N2][Ag4(H2hedp)2] (3) and [C4H12N2][Ag10(H2hedp)4(H2O)2]·2H2O (4) (H5hedp = 1-hydroxyethane-1,1-diphosphonic acid), have been pre
- Rom, Tanmay,Paul, Avijit Kumar
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p. 13618 - 13634
(2020/10/26)
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- Multinuclear Zn(II)-arylhydrazone complexes as catalysts for cyanosilylation of aldehydes
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Three known multinuclear Zn(II)-arylhydrazone complexes, [Zn{(CH3)2SO}(H2O)(L1)] (1), [Zn2(CH3OH)2(μ-L2)2] (2) and [Zn4(μ-OH)2(1κO:2κO
- Aliyeva, Vusala A.,Guseinov, Firudin I.,Ma, Zhen,Mahmudov, Kamran T.,Pombeiro, Armando J. L.,Tagiev, Dilgam B.,Zubkov, Fedor I.
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- Application of n-butyllithium in catalyzing cyanosilylation reaction of aldehyde and silane
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The invention discloses an application of n-butyllithium in catalyzing cyanosilylation reaction of aldehyde and silane. The n-butyllithium has high catalytic activity, low catalyst dosage and good substrate application range, and after n-butyllithium, ald
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Paragraph 0025-0027
(2020/07/02)
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- Transition Metal Ions Regulated Structural and Catalytic Behaviors of Coordination Polymers
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Three new coordination polymers (CPs), I [Cu(L)(H2O)]·2H2O, II [Zn(L)], and III [Ag(HL)(CH3CN)], were synthesized by employing a novel pyrazole-based dicarboxylate ligand (H2L) through a solvothermal strategy. Single-crystal structural analysis established that compounds I and II exhibit two-dimensional (2D) sheet structures, while compound III possesses a one-dimensional (1D) ladder structure due to the connectivity of terminal solvent moiety. The geometries of metal ions vary from square planar (Cu2+ ion) to distorted tetrahedral (Zn2+ and Ag+ ion). Topological study showed that compound I has made a (4·62)2(42·62·82) net, while compounds II and III have exposed common (44·62) SQL net and (42·6) net, respectively. The Lewis acidic nature of compounds I, II, and III has been confirmed with various heterogeneous catalytic reactions. For the first time, one-pot multicomponent synthesis of α-amino amidine has been performed by the three CPs and the reaction kinetics has been altered by the variation of Lewis acidic metal centers. The roles of metal ions for structural variations and the catalytic performances are investigated in a series of CPs.
- Kumar, Nikhil,Rom, Tanmay,Singh, Virender,Paul, Avijit Kumar
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p. 5277 - 5288
(2020/09/09)
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- Layered double hydroxides (LDHs): As efficient heterogeneous catalyst for the cyanosilylation of aromatic aldehydes
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We report the first application of Layered Double Hydroxides (LDHs) as efficient and novel heterogeneous catalyst for the cyanosilylation of aldehydes with excellent yields and simple work up. The reaction between different aldehydes with electron-withdra
- Afi, Fahimeh,Mokhtari, Javad,Tahoori, Fatemeh
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- N-Heterocyclic Germylene and Stannylene Catalyzed Cyanosilylation and Hydroboration of Aldehydes
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Recent years have witnessed a significant growth in the area of low-valent main-group compounds due to their potential to activate small molecules. However, there is a paucity of examples of low-valent main-group compounds being used as single-site cataly
- Dasgupta, Rajarshi,Das, Shubhajit,Hiwase, Shweta,Pati, Swapan K.,Khan, Shabana
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supporting information
p. 1429 - 1435
(2019/03/26)
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- PhI(OAc)2-mediated alkoxyoxygenation of β,γ-unsaturated ketoximes: Preparation of isoxazolines bearing two contiguous tetrasubstituted carbons
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A PhI(OAc)2-promoted dioxygenation of allyl oximes, including one alkoxylation, has been developed. This reaction can give isoxazoline products bearing two contiguous tetrasubstituted carbons. Various oximes substrates bearing different aryl groups and tetrasubstituted-olefin moieties were compatible with the mild reaction conditions. A two-electron oxidation pathway was proposed based on results of preliminary mechanistic studies.
- Ye, Chenghao,Kou, Xuezhen,Yang, Guoqiang,Shen, Jiefeng,Zhang, Wanbin
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supporting information
p. 1148 - 1152
(2019/03/26)
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- Two scandium coordination polymers: Rapid synthesis and catalytic properties
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Two scandium coordination polymers (Sc-CPs), [Sc(L1)2(DMF)] (DMF = N,N′-dimethyl formamide, H2L1 = pyrazine-2,3-dicarboxylic acid) (1) and [Sc(L2)(C2O4)0.5(H2/su
- Zhu, Ziqian,Tao, Yufang,Jiang, Yansong,Zhang, Liying,Xu, Jianing,Wang, Li,Fan, Yong
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p. 5261 - 5268
(2019/09/16)
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- Method for aldehyde cyanosilylation reaction under conditions of no catalyst or solvent
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The invention discloses a method for an aldehyde cyanosilylation reaction under conditions of no catalyst or solvent. In a glove box, aldehyde and trimethylsilyl cyanide are sequentially added to a nuclear magnetic resonance tube, then, the glove box is m
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Paragraph 0085; 0086; 0087; 0091
(2018/11/22)
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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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- Bifunctional 2D Cd(II)-Based Metal-Organic Framework as Efficient Heterogeneous Catalyst for the Formation of C-C Bond
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A porous two-dimensional (2D) metal-organic framework (MOF), namely, [Cd(PBA)(DMF)]·DMF (Cd-PBA), has been solvothermally synthesized by the reaction of 5-(4-pyridin-3-yl-benzoylamino)-isophthalic acid ligand (H2PBA) and Cd(II) ions. Structural
- Hu, Lei,Hao, Gui-Xia,Luo, Hai-Dong,Ke, Chun-Xian,Shi, Guang,Lin, Jia,Lin, Xiao-Ming,Qazi, Umair Yaqub,Cai, Yue-Peng
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p. 2883 - 2889
(2018/05/09)
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- Cyanosilylation of Aldehydes Catalyzed by Iron(III) Arylhydrazone-β-Diketone Complexes
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Two known iron(iii) complexes, [Fe(H2O)3(L1)]·xH2O (x≤4 (1), 5 (2)) and [Fe(H2O)3(L2)]·3H2O (3), bearing the basic forms of 5-chloro-3-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl)-2-hydroxybenzenesulfonic acid (H3L1) and 3-(2-(2,4-dioxopentan-3-y
- Gurbanov, Atash V.,Maharramov, Abel M.,Zubkov, Fedor I.,Saifutdinov, Alexander M.,Guseinov, Firudin I.
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p. 190 - 194
(2018/03/09)
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- Cyanosilylation of aldehydes catalyzed by mixed ligand copper(II) complexes
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The new mixed ligand copper(II) complexes [Cu(HL)(H2O)(A)]·2H2O (1, NaH2L = sodium (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazinyl)benzenesulfonate, A = dimethylsulfoxide, [Cu(HL)(H2O)(B)] (2, B =
- Gurbanov, Atash V.,Mahmoudi, Ghodrat,Guedes da Silva, M. Fátima C.,Zubkov, Fedor I.,Mahmudov, Kamran T.,Pombeiro, Armando J.L.
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p. 130 - 136
(2017/11/14)
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- Cyanosilylation of aldehydes catalyzed by lanthanide derivatives comprising arylhydrazones of β-diketones
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Two known lanthanide complexes, [KLa(HL1)2{(CH3)2NCHO}2(H2O)3] (1) and [Sm(H2O)9](E-H2L2)3·2H2O (2) were prepare
- Huseynov, Fatali E.,Shamilov, Nazim T.,Mahmudov, Kamran T.,Maharramov, Abel M.,Guedes da Silva, M.Fátima C.,Pombeiro, Armando J.L.
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p. 102 - 105
(2017/09/06)
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- Alkali metal complexes as efficient catalysts for hydroboration and cyanosilylation of carbonyl compounds
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We report here reactions between the N-adamantyliminopyrolyl ligand 2-(AdNCH)-C4H3NH (L-H) and alkali metal hexamethyldisilazides [MN(SiMe3)2] (M = Li, Na and K) to afford the dimeric [{2-(AdNCH)-C4H
- Harinath, Adimulam,Bhattacharjee, Jayeeta,Nayek, Hari Pada,Panda, Tarun K.
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supporting information
p. 12613 - 12622
(2018/09/27)
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- Cadmium-based metal organic framework material as well as preparation method and application thereof
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The invention discloses a cadmium-based metal organic framework material as well as a preparation method and an application thereof. The preparation method of the cadmium-based metal organic frameworkmaterial comprises steps as follows: 1) synthesis of li
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Paragraph 0094-0095; 0099
(2020/03/29)
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- Two Gd(III) coordination polymers based on a flexible tricarboxylate: Syntheses, structures, luminescence and catalytic properties
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Two Gadolinium coordination polymers {[Gd·(TTTA)·(H2O)2]·2H2O}n (1) and [Gd·(TTTA)·DMF]n (2) have been synthesized based on Gd(NO3)3·6H2O and the flexible tripodal lig
- Zhu, Yu,Zhu, Min,Liu, Pan,Xia, Li,Wu, Yunlong,Xie, Jimin
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- Copper(II) complexes with carboxylic- or sulfonic-functionalized arylhydrazones of acetoacetanilide and their application in cyanosilylation of aldehydes
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The new copper(II) complexes [Cu(HL1)(H2O)(CH3OH)] (1, H3L1?= (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazinyl)benzoic acid) and [Cu(HL2)(H2O)(CH3OH)] (2,
- Gurbanov, Atash V.,Mahmudov, Kamran T.,Sutradhar, Manas,Guedes da Silva, Fátima C.,Mahmudov, Talib A.,Guseinov, Firudin I.,Zubkov, Fedor I.,Maharramov, Abel M.,Pombeiro, Armando J.L.
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- Trinuclear and polymeric cobalt(II or II/III) complexes with an arylhydrazone of acetoacetanilide and their application in cyanosilylation of aldehydes
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The new trinuclear [CoII(H2O)2(Me2NCHO)2{CoIII(1κNOO′:2κO″-μ-HL)}2(1κNOO′)]·2H2O (1) and polymeric [CoII(1κNOO′:2κO″-μ-HL)(MeOH)2]n (2
- Gurbanov, Atash V.,Maharramov, Abel M.,Guedes da Silva, M. Fátima C.,Pombeiro, Armando J.L.
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p. 632 - 637
(2017/07/26)
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- Cyanosilylation of aldehydes catalyzed by arylhydrazone di- and triorganotin(IV) complexes
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Two known organotin(IV) complexes, [Sn(C6H5)3HL1] (1) and [Sn(C2H5)2(1κO,2κO-H3L2) (1κO2-H3L2) (μ3-O)]2/su
- Gurbanov, Atash V.,Huseynov, Fatali E.,Maharramov, Abel M.,Guedes da Silva, M. Fátima C.,Pombeiro, Armando J.L.
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p. 118 - 121
(2017/08/04)
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- Reaction of sodium 2-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl) benzenesulfonate with ethylenediamine on Cu(ii) and Ni(ii) centres: Efficient Cu(ii) homogeneous catalysts for cyanosilylation of aldehydes
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By reacting copper(ii) or nickel(ii) salts with sodium 2-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl) benzenesulfonate (NaHL) in an EtOH/H2O solvent mixture and in the presence of ethylenediamine (en), [Cu(HL)2(en)2] (1) or {
- Mahmoud, Abdallah G.,Mahmudov, Kamran T.,Guedes Da Silva, M. Fátima C.,Pombeiro, Armando J. L.
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p. 54263 - 54269
(2016/07/06)
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- A Polyhedral Metal-Organic Framework Based on Supramolecular Building Blocks: Catalysis and Luminescent Sensing of Solvent Molecules
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A multifunctional polyhedral metal-organic framework with a pcu network topology based on supramolecular building blocks can be constructed by the reaction of Eu(NO3)3 and pyridine-3,5-dicarboxylic acid (H2PDC). The basic
- Lin, Xiao-Ming,Niu, Ji-Liang,Wen, Pei-Xian,Pang, Ying,Hu, Lei,Cai, Yue-Peng
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p. 4705 - 4710
(2016/08/11)
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- Three scandium compounds with unsaturated coordinative metal sites - Structures and catalysis
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Two scandium coordination polymers, a 2D supermolecule structure {[Sc(OH)(L1)2(H2O)]}n (1) (HL1 = isonicotinic acid), a 1D infinite chain structure {[Sc3(L2)4(H2
- Zhang, Liying,Wang, Li,Wang, Pengcheng,Song, Tianyou,Li, Da,Chen, Xiaobo,Fan, Yong,Xu, Jianing
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p. 931 - 938
(2015/06/15)
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- Solvent-Induced Facile Synthesis of Cubic-, Spherical-, and Honeycomb-Shape Palladium N-Heterocyclic Carbene Particles and Catalytic Applications in Cyanosilylation
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The facile synthesis of palladium N-heterocyclic carbene (NHC) particles with spherical, cubic, and honeycomb morphologies is accomplished. The structures of cubic and honeycomb particles are defined as an unprecedented trinuclear palladium-NHC complex. A
- Zhao, Huaixia,Li, Xinxiong,Li, Liuyi,Wang, Ruihu
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p. 3642 - 3647
(2015/08/18)
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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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- Syntheses, structures, molecular and cationic recognitions and catalytic properties of two lanthanide coordination polymers based on a flexible tricarboxylate
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Two lanthanide coordination polymers, namely, {[La(TTTA)(H 2O)2]·2H2O}n (La-TTTA) and [Nd(TTTA)(H2O)2]·2H2O}n (Nd-TTTA) have been hydrothermally synthesized through th
- Zhu, Yu,Wang, Yan-Mei,Xu, Ji,Liu, Pan,Weththasinha,Wu, Yun-Long,Lu, Xiao-Qing,Xie, Ji-Min
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p. 259 - 264
(2014/11/12)
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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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- A 3D In(III) coordination polymer derived from rigid dicarboxylate ligand: Synthesis, crystal structure and catalytic property
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A new indium coordination polymer, In(OH)(H2O)(1,4-bdc) (1,4-H2bdc = 1, 4-benzendicarboxylic acid), has been prepared under solvothermal conditions using a mixture of rigid organic linker and inorganic heteropolyacid (12-phosphotungs
- Xia, Jing,Zheng, Jifu,Xu, Jianing,Wang, Li,Yang, Lu,Su, Zhandong,Fan, Yong
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- Tuning the catalytic activity of lanthanide-organic framework for the cyanosilylation of aldehydes
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Lanthanide-organic framework (LnMOF) [Eu2(MELL)(H 2O)6] (1) was rapidly produced via microwave-assisted hydrothermal synthesis and its performance as heterogeneous catalyst for the cyanosilylation of aldehydes was investig
- Batista, Poliane K.,Alves, Danilo J.M.,Rodrigues, Marcelo O.,De Sá, Gilberto F.,Junior, Severino A.,Vale, Juliana A.
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- Probing the bifunctional catalytic activity of ceria nanorods towards the cyanosilylation reaction
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Ceria nanorods were demonstrated to be an active, bifunctional catalyst for the cyanosilylation of aldehydes. The catalytic activity of ceria was shown to be positively correlated with a decrease in the coordination numbers of neighbouring oxygen atoms ar
- Wang, Gonghua,Wang, Lu,Fei, Xiang,Zhou, Yunyun,Sabirianov, Renat F.,Mei, Wai Ning,Cheung, Chin Li
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p. 2602 - 2609
(2013/09/24)
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- Kinetics and mechanism of the racemic addition of trimethylsilyl cyanide to aldehydes catalysed by Lewis bases
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The mechanism by which four Lewis bases, triethylamine, tetrabutylammonium thiocyanate, tetrabutylammonium azide and tetrabutylammonium cyanide, catalyse the addition of trimethylsilyl cyanide to aldehydes is studied by a combination of kinetic and spectr
- North, Michael,Omedes-Pujol, Marta,Young, Carl
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experimental part
p. 4289 - 4298
(2012/07/14)
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- Asymmetric cyanohydrin synthesis using an aluminium(salan) complex
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The asymmetric addition of trimethylsilyl cyanide to aldehydes catalysed by chiral metal(salan) complexes has been investigated. Salan complexes of titanium and vanadium displayed only low catalytic activity, but a bimetallic aluminium(salan) complex gave
- North, Michael,Stewart, Emma L.,Young, Carl
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p. 1218 - 1225,8
(2020/09/09)
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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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- Cooperative thiourea-Bronsted acid organocatalysis: Enantioselective cyanosilylation of aldehydes with TMSCN
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We report a new thiourea - Bronsted acid cooperative catalytic system for the enantioselective cyanosilylation of aldehydes with yields up to 90% and enantioselectivities up to 88%. The addition of an achiral acid was found to be crucial for high asymmetric induction. Mechanistic investigations using a combination of NMR, ESI-MS, and density functional theory computations (including solvent corrections) at the M06/6-31G(d,p) level of theory suggest that the key catalytic species results from the cooperative interaction of bifunctional thioureas and an achiral acid that form well-defined chiral hydrogen-bonding environments.
- Zhang, Zhiguo,Lippert, Katharina M.,Hausmann, Heike,Kotke, Mike,Schreiner, Peter R.
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experimental part
p. 9764 - 9776
(2012/01/03)
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- Investigation of lewis acid versus lewis base catalysis in asymmetric cyanohydrin synthesis
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The asymmetric addition of trimethylsilyl cyanide to aldehydes can be catalysed by Lewis acids and/or Lewis bases, which activate the aldehyde and trimethylsilyl cyanide, respectively. It is not always apparent from the structure of the catalyst whether Lewis acid or Lewis base catalysis predominates. To investigate this in the context of using salen complexes of titanium, vanadium and aluminium as catalysts, a Hammett analysis of asymmetric cyanohydrin synthesis was undertaken. When Lewis acid catalysis is dominant, a significantly positive reaction constant is observed, whereas reactions dominated by Lewis base catalysis give much smaller reaction constants. [{Ti(salen)O}2] was found to show the highest degree of Lewis acid catalysis, whereas two [VO(salen)X] (X = EtOSO3 or NCS) complexes both displayed lower degrees of Lewis acid catalysis. In the case of reactions catalysed by [{Al(salen)}2O] and triphenyl- phosphine oxide, a non-linear Ham- mett plot was observed, which is indicative of a change in mechanism with increasing Lewis base catalysis as the carbonyl compound becomes more electron-deficient. These results suggested that the aluminium complex/tri- phenylphosphine oxide catalyst system should also catalyse the asymmetric addition of trimethylsilyl cyanide to ke- tones and this was found to be the case.
- North, Michael,Omedes-Pujol, Marta,Williamson, Courtney
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experimental part
p. 11367 - 11375
(2010/11/17)
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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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- 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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