- η6-mesityl,η1-imidazolinylidene-carbene- ruthenium(II) complexes: Catalytic activity of their allenylidene derivatives in alkene metathesis and cycloisomerisation reactions
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The reaction of electron-rich carbene-precursor olefins containing two imidazolinylidene moieties [(2,4,6- Me3C6H2CH2)NCH2 CH2N(R)C=]2 (2a: R = CH2CH2OMe, 2
- Cetinkaya, Bekir,Demir, Serpil,Oezdemir, Ismail,Toupet, Loic,Semeril, David,Bruneau, Christian,Dixneuf, Pierre H.
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- Carbon-carbon bond forming reactions with substrates absorbed non-covalently on a cellulose chromatography paper support
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Reactions and purifications, including carbon-carbon bond forming reactions, can be carried out on a cellulose support on which the substrates are non-covalently absorbed. The Royal Society of Chemistry.
- Hacon, Jonathon,Morris, Amanda,Johnston, Michael J.,Shanahan, Stephen E.,Barker, Mike D.,Inglis, Graham G. A.,Macdonald, Simon J. F.
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- Organic-inorganic hybrid silica material derived from a monosilylated Grubbs-Hoveyda ruthenium carbene as a recyclable metathesis catalyst
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The synthesis of a monosilylated Grubbs-Hoveyda ruthenium alkylidene complex is described, as well as the preparation and characterization of the corresponding material by sol-gel cogelification with tetraethoxysilane (TEOS) and the assay of this recyclab
- Borja, Guadalupe,Pleixats, Roser,Alibes, Ramon,Cattoen, Xavier,Chi Man, Michel Wong
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- Olefin metathesis in supercritical carbon dioxide
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Liquid or supercritical carbon dioxide (scCO2) is a versatile reaction medium for ring-opening metathesis polymerization (ROMP) and ring-closing olefin metathesis (RCM) reactions using well-defined metal catalysts. The molybdenum alkylidene complex 1 and ruthenium carbenes 2 and 3 bearing PCy3 or N-heterocyclic carbene ligands, respectively, can be used and are found to exhibit efficiency similar to that in chlorinated organic solvents. While compound 1 is readily soluble in scCO2, complexes 2 and 3 behave like heterogeneous catalysts in this reaction medium. Importantly, however, the unique properties of scCO2 provide significant advantages beyond simple solvent replacement. This pertains to highly convenient workup procedures both for polymeric and low molecular weight products, to catalyst immobilization, to reaction tuning by density control (RCM versus acyclic diene metathesis polymerization), and to applications of scCO2 as a protective medium for basic amine functions. The latter phenomenon is explained by the reversible formation of the corresponding carbamic acid as evidenced by 1H NMR data obtained in compressed CO2. Together with its environmentally and toxicologically benign character, these unique physicochemical features sum up to a very attractive solvent profile of carbon dioxide for sustainable synthesis and production.
- Fuerstner,Ackermann,Beck,Hori,Koch,Langemann,Liebl,Six,Leitner
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- Immobilization of grubbs catalyst as supported ionic liquid catalyst (Ru-SILC)
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Grubbs olefin metathesis catalyst was immobilized as a ruthenium-supported ionic liquid catalyst (Ru-SILC) in pores of amorphous alumina with the aid of ionic liquid [hmim]PF6. This Ru-SILC was effective for various olefin metathesis reactions
- Hagiwara, Hisahiro,Okunaka, Naotaro,Hoshi, Takashi,Suzuki, Toshio
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- Occlusion of Grubbs' catalysts in active membranes of polydimethylsiloxane: Catalysis in water and new functional group selectivities
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The Grubbs' first and second generation catalysts were occluded into cross-linked slabs of polydimethylsiloxane with volumes from 1 mm3 to 1 cm3 by swelling the polymer with catalyst and methylene chloride. Methylene chloride was evaporated under vacuum to yield occluded catalysts where their solvent was polydimethylsiloxane. These occluded catalysts were reacted with alkenes dissolved in H2O or H2O/MeOH mixtures that diffused into the polydimethylsiloxane to react by ring-closing metathesis and cross metathesis. Control experiments revealed that the catalysts remained occluded and metathesis did not occur in the solvent. Occlusion of these catalysts allowed commercially available Grubbs' catalysts to be used with H2O as the solvent while isolating the H2O sensitive ruthenium methylidene from exposure to H2O. Functional group selective experiments were carried out where the polydimethylsiloxane was an "active" membrane to exclude salts. Polydimethylsiloxane is a hydrophobic polymer, so the deprotonated salt of diallylmalonic acid did not diffuse into it while a diallylether diffused into it and reacted by metathesis. Thus, by controlling the polarity of reagents their reactivity can be controlled owing to the properties of polydimethylsiloxane rather than those of the Grubbs' catalysts. Occlusion of catalysts in polydimethylsiloxane has been shown to add new selectivities to mature catalysts. Copyright
- Mwangi, Martin T.,Runge, M. Brett,Bowden, Ned B.
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- Olefin metathesis catalyst bearing a chelating phosphine ligand
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An improved synthetic procedure for the complex (SPY-5-34)-dichloro- (κ2(C,P)-diphenyl-(2-benzylidene)-phosphine)-(1,3-bis(2,4, 6-trimethylphenyl)-4,5-dihydro-imidazol-2-ylidene)-ruthenium (2) was elaborated and the title compound was tested as
- Lexer, Christina,Burtscher, Daniel,Perner, Bernhard,Tzur, Eyal,Lemcoff, N. Gabriel,Slugovc, Christian
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- Metathesis in pure water mediated by supramolecular additives
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Supramolecular, water-soluble additives based on calix[n] arenes exhibit a beneficial influence on the ring-closing and cross metathesis of non-polar substrates in pure aqueous medium using standard Grubbs-II and Hoveyda-II catalysts. The catalytic activi
- Brendgen, Thomas,Fahlbusch, Tilmann,Frank, Markus,Schuehle, Daniel T.,Sessler, Miriam,Schatz, Juergen
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- Mixed N-heterocyclic carbene/phosphite ruthenium complexes: Towards a new generation of olefin metathesis catalysts
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The synthesis, characterisation and catalytic behaviour of ruthenium indenylidene complexes bearing an N-heterocyclic carbene and triisopropylphosphite are described.
- Bantreil, Xavier,Schmid, Thibault E.,Randall, Rebecca A. M.,Slawin, Alexandra M. Z.,Cazin, Catherine S. J.
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- An unusual cationic Ru(ii) indenylidene complex and its Ru(iii) derivative - Efficient catalysts for high temperature olefin metathesis reactions
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The use of a mixed phosphite/N-heterocyclic carbene bearing ruthenium precursor permits the synthesis and characterisation of unprecedented four-coordinate Ru(ii) and Ru(iii) cationic complexes adopting an unusual sawhorse structure. The cationic Ru(ii) c
- Songis, Olivier,Slawin, Alexandra M. Z.,Cazin, Catherine S. J.
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- Ruthenium-catalyzed olefin metathesis in ionic liquids
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Figure presented Ionic liquid 1-butyl-3-methylimidazoliumhexafluorophosphate ([bmim]PF6) is described as an effective medium for ring-closing metathesis (RCM) using Grubbs catalysts. When [bmim]PF6 was used as solvent, the RCM showed
- Buijsman, Rogier C.,Van Vuuren, Elizabeth,Sterrenburg, Jan Gerard
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- A convenient method for the efficient removal of ruthenium byproducts generated during olefin metathesis reactions.
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[reaction in text] An efficient method for removing ruthenium byproducts generated during olefin metathesis reactions with Grubbs catalysts is described. Treatment of the crude reaction products with triphenylphosphine oxide or dimethyl sulfoxide, followe
- Ahn,Yang,Georg
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- Allenyl esters as quenching agents for ruthenium olefin metathesis catalysts
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In the attempt to synthesize substituted allenyl esters through a metathesis coupling of unsubstituted allenyl esters and alkenes using a variety of ruthenium catalysts, it was discovered that allenyl esters themselves cleanly arrested the activity of the catalysts. Further studies suggests possible utility of allene esters as general quenching agents for metathesis reactions. To explore this idea, several representative olefin metathesis reactions, including ring closing, were successfully terminated by the addition of simple allenyl esters for more convenient purification.
- Roy, Animesh,Silvestri, Maximilian A.,Hall, Robert A.,Lepore, Salvatore D.
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- Ring-closing metathesis reactions: Interpretation of conversion-time data
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Conversion-time data were recorded for various ring-closing metathesis (RCM) reactions that lead to five- or six-membered cyclic olefins by using different precatalysts of the Hoveyda type. Slowly activated precatalysts were found to produce more RCM product than rapidly activated complexes, but this comes at the price of slower product formation. A kinetic model for the analysis of the conversion-time data was derived, which is based on the conversion of the precatalyst (Pcat) into the active species (Acat), with the rate constant kact, followed by two parallel reactions: 1) the catalytic reaction, which utilizes Acat to convert reactants into products, with the rate k cat, and 2) the conversion of Acat into the inactive species (Dcat), with the rate kdec. The calculations employ two experimental parameters: the concentration of the substrate (c(S)) at a given time and the rate of substrate conversion (-dc(S)/dt). This provides a direct measure of the concentration of Acat and enables the calculation of the pseudo-first-order rate constants kact, kcat, and kdec and of k S (for the RCM conversion of the respective substrate by Acat). Most of the RCM reactions studied with different precatalysts are characterized by fast kcat rates and by the kdec value being greater than the kact value, which leads to quasistationarity for Acat. The active species formed during the activation step was shown to be the same, regardless of the nature of different Pcats. The decomposition of Acat occurs along two parallel pathways, a unimolecular (or pseudo-first-order) reaction and a bimolecular reaction involving two ruthenium complexes. Electron-deficient precatalysts display higher rates of catalyst deactivation than their electron-rich relatives. Slowly initiating Pcats act as a reservoir, by generating small stationary concentrations of Acat. Based on this, it can be understood why the use of different precatalysts results in different substrate conversions in olefin metathesis reactions. Copyright
- Thiel, Vasco,Wannowius, Klaus-Juergen,Wolff, Christiane,Thiele, Christina M.,Plenio, Herbert
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- Ruthenium catalysts bearing chelating carboxylate ligands: application to metathesis reactions in water
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The novel catalytic system, composed of a ruthenium alkylidene containing a surfactant fragment in the catalysts molecule, is reported. Ring closing metathesis and cross metathesis reactions proceed efficiently in neat water at room temperature, in air, without need of adding an external surfactant.
- Gawin, Rafa?,Czarnecka, Patrycja,Grela, Karol
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- GaCl3-catalyzed allenyne cycloisomerizations to allenenes
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Cycloisomerizations of allenynes to allenenes have been studied in the presence of catalytic amounts of [Au(PPh3)]-SbF6 in dichloromethane or GaCl3 in toluene. Both catalytic systems are quite effective for terminal 1,6-al
- Lee, Sang Ick,Sim, So Hee,Kim, Soo Min,Kim, Kwang,Chung, Young Keun
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- Non covalent immobilization of pyrene-tagged ruthenium complexes onto graphene surfaces for recycling in olefin metathesis reactions
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Synthesis of Hoveyda-type ruthenium complexes, modified by pyrene tags on the NHC ligand and/or the benzylidene moiety, is described. Thanks to non-covalent π-π interactions these new complexes were immobilized on carbon supports [reduced graphene oxide (rGO) or graphene] and their activity and recoverability for metatheses reactions have been studied. A SIPr-based complex possessing the pyrene function on the benzylidene ligand (C2) delivered the best results for the ring closing metathesis of diethyldiallyl malonate as benchmark reaction. The presence of additional pyrene-functionalized styrenyl-ether as ligand to the rGO-supported catalyst (C2/L@rGO) noticeably improved the recycling procedure allowing supplementary efficient catalytic runs. This may be due either to a facilitated boomerang effect or to a gradual release of the active species in solution. Finally, catalyst C2/L@rGO was proven to be successfully used to promote metathesis reactions in a multisubstrate procedure, the same supported-catalyst batch being successively engaged to transform three different substrates, in diene and ene-yne RCM reactions.
- Nasrallah, Houssein,Germain, Stéphane,Queval, Pierre,Bouvier, Caroline,Mauduit, Marc,Crévisy, Christophe,Schulz, Emmanuelle
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- Immobilisation of the Grubbs III olefin metathesis catalyst with polyvinyl pyridine (PVP)
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A new concept for immobilising Grubbs III catalyst by direct coordination of ruthenium to poly vinyl pyridine (PVP) is presented. PVP was prepared by precipitation polymerisation, which led to small bead sizes (0.2-2 μm) and large surface areas. Compared
- Mennecke, Klaas,Grela, Karol,Kunz, Ulrich,Kirschning, Andreas
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- A dormant ruthenium catalyst bearing a chelating carboxylate ligand: In situ activation and application in metathesis reactions
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(Chemical Equation Presented) Sleeping beauty: A dormant catalyst, 1, can be activated in situ by various acids (HA) to form complexes 2 of high activity in olefin metathesis. After the reaction and when subjected to silica gel chromatography, these catalysts are readily transformed back into 1. This system shows a high degree of tunability and excellent applicability in model metathesis reactions.
- Gawin, Rafal,Makal, Anna,Wozniak, Krzysztof,Mauduit, Marc,Grela, Karol
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- A Thermo- and Photo-Switchable Ruthenium Initiator for Olefin Metathesis
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A ruthenium carbene complex bearing azobenzene functionality is reported. The complex exists in the form of two isomers differing by the size of the chelate ring. Both isomers were isolated by applying kinetic or thermodynamic control during the synthesis and characterized by X-ray diffraction analysis. The isomerization of the complex was studied by UV/Vis spectroscopy. The stable isomer was tested as a catalyst in olefin metathesis. The complex was activated at about 100°C to promote ring-closing and ring-opening polymerization metathesis reactions. The activation took place also at room temperature under middle ultraviolet radiation.
- Sashuk, Volodymyr,Danylyuk, Oksana
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- Nucleophile dependent formation of 6- and 7-membered: N -heterocycles by platinum-catalysed cyclisation of 1,5-bisallenes
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An unprecedented Pt-catalysed cyclisation of N-tethered 1,5-bisallenes in the presence of oxygen nucleophiles is reported, where formation of 6- or 7-membered rings is driven by the choice of nucleophile and the mechanism dictated by the nucleophile and the electronic properties of the bisallene. The reaction in the presence of alcohols gives preferentially vinyltetrahydropyridines with an extra alkoxy group and Pt-H as the active species in the catalytic cycle, while formation of di- and tetrahydroazepines with an extra hydroxyl group is favoured when water is used as nucleophile, via nucleophilic attack/carbocyclization as the favoured pathway. The products obtained are frequently found in the core of natural products with important biological activities, so understanding this complex mechanistic behaviour and exploiting this new methodology will have a big impact in organic synthesis and organometallic chemistry.
- Quirós, María Teresa,Hurtado-Rodrigo, César,Mu?oz, María Paz
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- Potassium carbonate-promoted stereospecific 5-endo-trig cyclization of unactivated allenes in the absence of any transition metals
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Formation of 3-pyrrolines from simple unactivated allenes bearing a protected amino group under basic conditions is described. Treatment of α-amino allenes with potassium carbonate in DMF under reflux in the absence of any transition-metal catalysts gave
- Ohno, Hiroaki,Kadoh, Yoichi,Fujii, Nobutaka,Tanaka, Tetsuaki
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- Fluorous phase-transfer activation of catalysts: Application of a new rate-enhancement strategy to alkene metathesis
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Reactions of the bis(pyridine) complex (H2IMes)(Py) 2(Cl)2Ru(=CHPh) and fluorous phosphines P(CH 2CH2Rfn)3 (n = a, 6; b, 8; c, 10; Rfn = (CF2)n-1
- Correa Da Costa, Rosenildo,Gladysz
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- Removable Water-Soluble Olefin Metathesis Catalyst via Host-Guest Interaction
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A highly removable N-heterocyclic carbene ligand for a transition-metal catalyst in aqueous media via host-guest interactions has been developed. Water-soluble adamantyl tethered ethylene glycol in the ligand leads a hydrophobic inclusion into the cavity of β-cyclodextrin. Ruthenium (Ru) olefin metathesis catalyst with this ligand demonstrated excellent performance in various metathesis reactions in water as well as in CH2Cl2, and removal of residual Ru was performed via filtration utilizing a host-guest interaction and extraction.
- Kim, Cheoljae,Ondrusek, Brian A.,Chung, Hoyong
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- Model studies towards kainic acid
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A novel photochemical approach to the kainoid ring system is presented alongside model studies to demonstrate its feasibility.
- Greenwood,Parsons
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- Ionic Liquids, 3. Synthesis and Utilisation of Protic Imidazolium Salts in Homogeneous Catalysis
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Protonation of 1-alkylimidazoles provides halogen-free salts which act as ionic liquids and proton reservoir in proton- and metal-assisted catalytic processes like dimerisation of methyl acrylate and ring closing metathesis, and lead to significant improvements both in activity and selectivity.
- Picquet, Michel,Tkatchenko, Igor,Tommasi, Immacolata,Wasserscheid, Peter,Zimmermann, Joerg
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- Ring-Closing Olefin Metathesis Catalyzed by Well-Defined Vanadium Alkylidene Complexes
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Vanadium-based catalysts have shown activity and selectivity in ring-opening metathesis polymerization of strained cyclic olefins comparable to those of Ru, Mo, and W catalysts. However, the application of V alkylidenes in routine organic synthesis is limited. Here, we present the first example of ring-closing olefin metathesis catalyzed by well-defined V chloride alkylidene phosphine complexes. The developed catalysts exhibit tolerance to various functional groups, such as an ether, an ester, a tertiary amide, a tertiary amine, and a sulfonamide. The size and electron-donating properties of the imido group and the phosphine play a crucial role in the stability of active intermediates. Reactions with ethylene and olefins suggest that both β-hydride elimination of the metallacyclobutene and bimolecular decomposition are responsible for catalyst degradation.
- Belov, Dmitry S.,Tejeda, Gabriela,Tsay, Charlene,Bukhryakov, Konstantin V.
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supporting information
p. 4578 - 4582
(2021/02/11)
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- Synthesis of Vanadium Oxo Alkylidene Complex and Its Reactivity in Ring-Closing Olefin Metathesis Reactions
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V imido alkylidenes have been applied for the ring-opening metathesis polymerization involving cyclic olefins. However, those complexes found limited application in reactions with acyclic terminal olefins due to instability toward ethylene. Experimental and theoretical studies show that the β-hydride elimination from unsubstituted metallacyclobutene is the primary decomposition pathway in those systems. Herein, we report the synthesis of the first catalytically active V oxo alkylidene, VO(CHSiMe3)(PEt3)2Cl, which exhibits the highest reported productivity with various terminal olefins in ring-closing metathesis reactions among known V catalysts. Presented DFT studies indicate that β-hydride elimination is significantly disfavored for V oxo species.
- Belov, Dmitry S.,Bukhryakov, Konstantin V.,Chakraborty, Indranil,Fenoll, Didac A.,Solans-Monfort, Xavier
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supporting information
p. 2939 - 2944
(2021/09/13)
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- Synthetic method of 3-aminopyrrolidine hydrochloride
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The invention discloses a synthetic method of 3-aminopyrrolidine hydrochloride. The synthetic method comprises the steps: S1, carrying out cyclization reaction on a compound I and a compound II to obtain a compound III; S2, reacting the compound III under the action of hydrogen halide gas to obtain a compound IV; S3, reacting the compound IV with organic sulfonamide in the presence of alkali to obtain a compound V; and S4, reacting the compound V with acid to obtain a compound VI. According to the synthetic method of the 3-aminopyrrolidine hydrochloride, aryl and alkyl sulfonic groups are introduced to protect two amino groups, and during deprotection, a single reaction condition can be used, so that operation steps are effectively reduced; when benzyl is used for protecting ammonia, precious metal palladium and high-pressure catalytic hydrogenation are used for deprotection, the production cost is high, the operation risk is high, aryl and alkane sulfonic groups are used for protection, only acid is used for catalytic hydrolysis for deprotection, and the reaction condition is mild.
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Paragraph 0092-0095; 0099-0102
(2021/03/31)
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- Activated Hoveyda-Grubbs Olefin Metathesis Catalysts Derived from a Large Scale Produced Pharmaceutical Intermediate – Sildenafil Aldehyde
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Two EWG-activated Hoveyda-Grubbs-type ruthenium complexes (Sil-II and Sil-II’) were obtained, characterized, and screened in a set of olefin metathesis reactions. These catalysts were conveniently synthesized from a commercially available pharmaceutical building block – Sildenafil aldehyde – in two steps only. Stability and catalytic activity tests disclosed that the bulkier NHC-ligand bearing catalyst Sil-II’ is visibly more stable and productive than its smaller NHC-analogue Sil-II. Good application profile of catalyst Sil-II’ was confirmed in a set of diverse metathesis reactions including ring-closing metathesis (RCM) and cross-metathesis (CM) of complex polyfunctional substrates of medicinal chemistry interest, including a challenging macrocyclization of the Pacritinib precursor. Compatibility of the new catalyst with various green solvents was checked and metathesis of Sildenafil and Tadalafil-based substrates was successfully conducted in acetone. The mechanism of Sil-II’ initiation has been investigated through kinetic experiments unveiling that the decrease of the steric hindrance of the chelating alkoxy moiety (from iPrO to EtO) favors the interchange initiation pathway over the typical dissociation pathway for other popular 2nd generation Hoveyda-Grubbs catalysts. (Figure presented.).
- Monsigny, Louis,Pi?tkowski, Jakub,Trzybiński, Damian,Wo?niak, Krzysztof,Niena?towski, Tomasz,Kajetanowicz, Anna,Grela, Karol
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supporting information
p. 4590 - 4604
(2021/08/13)
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- One-pot chemoenzymatic reactions in water enabled by micellar encapsulation
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The use of micellar conditions to enable one-pot reactions involving both transition metal and enzymatic catalysts is reported. Representative enzymatic transformations under micellar conditions are unaffected by the presence of non-ionic surfactants, including designer surfactants such as TPGS-750-M. Furthermore, the presence of enzymes has a negligible effect on transition metal catalysis under micellar conditions in water. Finally, three one-pot chemoenzymatic reactions in water are reported in which the micelle-forming surfactant TPGS-750-M is a crucial factor for reaction efficiency.
- Adams, Nicholas P.,Bushi, Jurgen,Hastings, Courtney J.,Kolb, Samuel J.
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p. 6187 - 6193
(2020/10/18)
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- Synthesis of N -Sulfonyl- and N -Acylpyrroles via a Ring-Closing Metathesis/Dehydrogenation Tandem Reaction
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N -Sulfonyl- and N -acylpyrroles were synthesized via olefin ring-closing metathesis of diallylamines and in situ oxidative aromatization in the presence of the ruthenium Grubbs catalyst and a suitable copper catalyst. In the presence of Cu(OTf) 2/s
- Chen, Weiqiang,Li, Hui-Jing,Liu, Ying,Nan, Xiang,Wu, Yan-Chao,Zhang, Yin-Lin
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p. 3651 - 3666
(2019/09/30)
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- Hoveyda–Grubbs catalysts with an N→Ru coordinate bond in a six-membered ring. Synthesis of stable, industrially scalable, highly efficient ruthenium metathesis catalysts and 2-vinylbenzylamine ligands as their precursors
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A novel and efficient approach to the synthesis of 2-vinylbenzylamines is reported. This involves obtaining 2-vinylbenzylamine ligands from tetrahydroisoquinoline by alkylation and reduction followed by the Hofmann cleavage. The resultant 2-vinylbenzyl-amines allowed us to obtain new Hoveyda–Grubbs catalysts, which were thoroughly characterised by NMR, ESIMS, and X-ray crystallography. The utility of this chemistry is further demonstrated by the tests of the novel catalysts (up to 10?2 mol %) in different metathesis reactions such as cross metathesis (CM), ring-closing metathesis (RCM) and ring-opening cross metathesis (ROCM).
- Polyanskii, Kirill B.,Alekseeva, Kseniia A.,Raspertov, Pavel V.,Kumandin, Pavel A.,Nikitina, Eugeniya V.,Gurbanov, Atash V.,Zubkov, Fedor I.
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supporting information
p. 769 - 779
(2019/04/17)
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- CRYSTAL AND SALT OF NITROIMIDAZOLE, AND MANUFACTURING METHOD THEREOF
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The present invention discloses a crystal form and salt of a nitroimidazole compound, and a manufacturing method thereof. The invention further comprises an application of the crystal form and salt in preparing a pharmaceutical product for preventing and treating an infection caused by Mycobacterium tuberculosis or another microbe.
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Paragraph 0087; 0090-0091
(2019/09/20)
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- Semiheterogeneous Purification Protocol for the Removal of Ruthenium Impurities from Olefin Metathesis Reaction Products Using an Isocyanide Scavenger
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A low-waste, time-economical, and scalable semiheterogeneous purification protocol for the removal of ruthenium residues from olefin metathesis (OM) reactions has been developed. It is based on the non-covalent immobilization of the commercially available
- Szczepaniak, Grzegorz,Noga?, Wojciech,Piatkowski, Jakub,Ruszczyńska, Anna,Bulska, Ewa,Grela, Karol
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supporting information
p. 836 - 844
(2019/04/17)
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- Visible-Light-Controlled Ruthenium-Catalyzed Olefin Metathesis
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Olefin metathesis is now one of the most efficient ways to create new carbon-carbon bonds. While most efforts focused on the development of ever-more efficient catalysts, a particular attention has recently been devoted to developing latent metathesis cat
- Theunissen, Cédric,Ashley, Melissa A.,Rovis, Tomislav
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supporting information
(2019/05/08)
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- Visible-Light-Controlled Ruthenium-Catalyzed Olefin Metathesis
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Olefin metathesis is now one of the most efficient ways to create new carbon-carbon bonds. While most efforts focused on the development of ever-more efficient catalysts, a particular attention has recently been devoted to developing latent metathesis cat
- Theunissen, Cédric,Ashley, Melissa A.,Rovis, Tomislav
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supporting information
p. 6791 - 6796
(2019/05/10)
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- Ethyl Lactate: A Green Solvent for Olefin Metathesis
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Compatibility of selected, commercially available ruthenium olefin metathesis catalysts with ethyl lactate as solvent was evaluated using a range of substrates and conditions. In addition, the preparation of a metathesis catalyst in simplified manner by u
- Planer, Sebastian,Jana, Anupam,Grela, Karol
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p. 4655 - 4661
(2019/10/28)
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- Ammonium NHC-tagged olefin metathesis catalysts-influence of counter-ions on catalytic activity
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Ruthenium-based catalysts bearing quaternary ammonium groups in their N-heterocyclic carbene (NHC) fragments and different counter-ions were synthesised and tested in various olefin metathesis transformations. Differences in catalytic activity in correlation with the nature of the present counter-ion were revealed. The unique properties of the described catalysts allow for the effective preparation of a variety of metathesis products with low ruthenium contamination and under green chemistry conditions.
- Tracz, Andrzej,Gawin, Anna,Bieniek, Micha?,Olszewski, Tomasz K.,Skowerski, Krzysztof
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supporting information
p. 8609 - 8614
(2018/06/08)
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- Nitrogen-coordination-containing ruthenium carbene catalyst and preparation method and application thereof
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The present invention discloses a nitrogen-coordination-containing ruthenium carbene catalyst and a preparation method and application thereof. The nitrogen-coordination-containing ruthenium carbene catalyst is characterized by being shown in a formula (I
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Paragraph 0077; 0078; 0079; 0080; 0112
(2018/11/22)
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- Carboxyl Graphene as a Superior Support for Bulky Ruthenium-Based Olefin Metathesis Catalyst
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A Hoveyda-type catalyst decorated with two quaternary ammonium tags was synthesized and noncovalently grafted on SiO2, SBA-15, and on carboxyl graphene. A comparative study showed that the efficiency of the dual-anchored heterogeneous catalysts was highly dependent on the properties of the supporting material with graphene outperforming silicate supports. The graphene-immobilized complex exhibited excellent efficiency reflected in turnover numbers obtained in ring-closing metathesis and in self-metathesis of 1-decene. Importantly, the solid-supported catalyst assured increased recyclability with no ruthenium leaching as confirmed by inductively coupled plasma mass spectrometry.
- Kaczanowska, Katarzyna,Chwalba, Micha?,Pastva, Jakub,Kub?, Martin,Ruszczyńska, Anna,Bulska, Ewa,Balcar, Hynek,Skowerski, Krzysztof
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p. 1837 - 1844
(2018/07/05)
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- ANTI-PULMONARY TUBERCULOSIS NITROIMIDAZOLE DERIVATIVE
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Disclosed is a substituted nitroimidazole derivative, which is mainly used for treating related diseases caused by mycobacterial infections, such as Mycobacterium tuberculosis, especially being suitable for diseases caused by resistant Mycobacterium tuberculosis.
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Paragraph 0614; 0617; 0618
(2017/12/31)
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- A nitrogen-containing cyclic olefin compound (by machine translation)
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[A] a method of efficiently producing the nitrogen-containing cyclic olefin compound. [Solution] the low valent niobium complex, (I) the formula represented by protective diallylamine N -, (II) a nitrogen-containing cyclic olefin compound represented by t
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Paragraph 0052
(2017/07/31)
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- New, potentially chelating NHC ligands; synthesis, complexation studies, and preliminary catalytic evaluation
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Two new N-heterocyclic carbene (NHC) ligands bearing 2-morpholino and 2-piperidinyl naphthyl wingtips were synthesised (2-SIMorNap and 2-SIPipNap). Nuclear magnetic resonance studies, in conjunction with crystal structures and derivatisation of the NHC salts using a chiral counteranion, revealed that the ligand wingtips are oriented anti with respect to each other. From the free carbene, palladium, ruthenium and iridium complexes were prepared. NHC-iridium dicarbonyl complexes were made in order to extract the TEP values for these ligands. The study showed that these NHC ligands are more electron-donating than normal, aryl-substituted NHCs. The palladium complexes were tested in representative Suzuki-Miyaura cross-coupling reactions and compared to the state of the art systems. Ruthenium-catalysed ring-closing metathesis with these ligands was also performed. It was found that Grubbs’ 2nd generation catalyst incorporating 2-SIPipNap did not initiate at room temperature and required heating for RCM to occur.
- Ou, Arnold,Wu, Linglin,Salvador, Alvaro,Sipos, Gellert,Zhao, Guangzhen,Skelton, Brian W.,Sobolev, Alexandre N.,Dorta, Reto
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supporting information
p. 3631 - 3641
(2017/03/22)
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- Dual-role of PtCl2 catalysis in the intramolecular cyclization of (hetero)aryl-allenes for the facile construction of substituted 2,3-dihydropyrroles and polyheterocyclic skeletons
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A Pt(ii)-catalyzed cyclization of (hetero)aryl-allenes has been developed, providing controllable synthesis of substituted 2,3-dihydropyrroles and polyheterocyclic skeletons. Another notable feature of this method is the dual-role of the Pt(ii) catalyst: initiation of the migration of the (hetero)arylmethylene group and the subsequent Friedel-Crafts type annulation.
- Zhang, Yan-Yan,Wei, Yin,Tang, Xiang-Ying,Shi, Min
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p. 5966 - 5969
(2017/07/11)
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- Preference of Ruthenium-Based Metathesis Catalysts toward Z- and E-Alkenes as a Guide for Selective Reactions to Alkene Stereoisomers
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As a guide for selective reactions toward either Z- or E-alkene in a metathesis reaction, the relative preference of metathesis Ru catalysts for each stereoisomer was determined by a method using time-dependent fluorescence quenching. We found that Ru-1 p
- Lee, Jihong,Kim, Kyung Hwan,Lee, Ok Suk,Choi, Tae-Lim,Lee, Hee-Seung,Ihee, Hyotcherl,Sohn, Jeong-Hun
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p. 7591 - 7596
(2016/09/09)
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- The Discovery of Quinoxaline-Based Metathesis Catalysts from Synthesis of Grazoprevir (MK-5172)
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Olefin metathesis (OM) is a reliable and practical synthetic methodology for challenging carbon-carbon bond formations. While existing catalysts can effect many of these transformations, the synthesis and development of new catalysts is essential to increase the application breadth of OM and to achieve improved catalyst activity. The unexpected initial discovery of a novel olefin metathesis catalyst derived from synthetic efforts toward the HCV therapeutic agent grazoprevir (MK-5172) is described. This initial finding has evolved into a class of tunable, shelf-stable ruthenium OM catalysts that are easily prepared and exhibit unique catalytic activity.
- Williams, Michael J.,Kong, Jongrock,Chung, Cheol K.,Brunskill, Andrew,Campeau, Louis-Charles,McLaughlin, Mark
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supporting information
p. 1952 - 1955
(2016/06/01)
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- Effective immobilisation of a metathesis catalyst bearing an ammonium-tagged NHC ligand on various solid supports
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An ammonium-tagged ruthenium complex, 8, was deposited on several widely available commercial solid materials such as silica gel, alumina, cotton, filter paper, iron powder or palladium on carbon. The resulting catalysts were tested in toluene or ethyl acetate, and found to afford metathesis products in high yield and with extremely low ruthenium contamination. Depending on the support used, immobilised catalyst 8 shows also additional traits, such as the possibility of being magnetically separated or the use for metathesis and subsequent reduction of the obtained double bond in one pot.
- Skowerski, Krzysztof,Biatecki, Jacek,Czarnocki, Stefan J.,Zukowska, Karolina,Grela, Karol
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supporting information
p. 5 - 15
(2016/04/05)
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- Nitro-Grela-type complexes containing iodides -robust and selective catalysts for olefin metathesis under challenging conditions
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Iodide-containing nitro-Grela-type catalysts have been synthesized and applied to ring closing metathesis (RCM) and cross metathesis (CM) reactions. These new catalysts have exhibited improved efficiency in the transformation of sterically, nondemanding a
- Tracz, Andrzej,Matczak, Mateusz,Urbaniak, Katarzyna,Skowerski, Krzysztof
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supporting information
p. 1823 - 1832
(2016/04/19)
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- A medium fluorous Grubbs-Hoveyda 2nd generation catalyst for phase transfer catalysis of ring closing metathesis reactions
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A fluorous Grubbs-Hoveyda metathesis catalyst supported on Teflon powder, that readily moves between the solid phase (Teflon) and the liquid phase (DMF) was prepared. By modulating the hydrophobicity of the reaction medium at the end of the reaction, the supported catalyst could be recovered by simple filtration even though the catalyst existed in a homogeneous state during the reaction. In RCM reactions, the catalyst could be reused up to three times with only a slight loss in reactivity with each subsequent cycle.
- Kobayashi, Yuki,Inukai, Sae,Kondo, Natsuki,Watanabe, Tomoko,Sugiyama, Yuya,Hamamoto, Hiromi,Shioiri, Takayuki,Matsugi, Masato
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p. 1363 - 1366
(2015/03/04)
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- Origins of initiation rate differences in ruthenium olefin metathesis catalysts containing chelating benzylidenes
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A series of second-generation ruthenium olefin metathesis catalysts was investigated using a combination of reaction kinetics, X-ray crystallography, NMR spectroscopy, and DFT calculations in order to determine the relationship between the structure of the chelating o-alkoxybenzylidene and the observed initiation rate. Included in this series were previously reported catalysts containing a variety of benzylidene modifications as well as four new catalysts containing cyclopropoxy, neopentyloxy, 1-adamantyloxy, and 2-adamantyloxy groups. The initiation rates of this series of catalysts were determined using a UV/vis assay. All four new catalysts were observed to be faster-initiating than the corresponding isopropoxy control, and the 2-adamantyloxy catalyst was found to be among the fastest-initiating Hoveyda-type catalysts reported to date. Analysis of the X-ray crystal structures and computed energy-minimized structures of these catalysts revealed no correlation between the Ru-O bond length and Ru-O bond strength. On the other hand, the initiation rate was found to correlate strongly with the computed Ru-O bond strength. This latter finding enables both the rationalization and prediction of catalyst initiation through the calculation of a single thermodynamic parameter in which no assumptions about the mechanism of the initiation step are made.
- Engle, Keary M.,Lu, Gang,Luo, Shao-Xiong,Henling, Lawrence M.,Takase, Michael K.,Liu, Peng,Houk,Grubbs, Robert H.
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p. 5782 - 5792
(2015/05/20)
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- Synthesis and catalytic activity of a Grubbs-Hoveyda pre-catalyst having a trimeric resting state
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A Grubbs-Hoveyda pre-catalyst having a trimeric resting state based on 2,4,6-trichloro-1,3,5-triazine was synthesized and the complex was characterized by NMR, HRMS and elemental analysis. The activity of this complex for ring-closing metathesis (RCM) was
- Liu, Guiyan,Wu, Bin,Wang, Jianhui
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p. 441 - 445
(2015/04/22)
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- Synthesis and catalytic study of ruthenium carbene catalyst containing a Zn-porphyrin ligand
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A ruthenium carbene complex containing a Zn-porphyrin ligand has been developed. The complex was characterized by 1H NMR, IR, HRMS and elemental analysis. The catalytic activity of the ruthenium carbene complex for olefin metathesis reactions w
- Xu, Ying,Zhang, Huizhu,Wang, Xinyuan,Liu, Guiyan
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p. 1393 - 1397
(2016/02/18)
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- Latent ruthenium-indenylidene catalysts bearing a N-heterocyclic carbene and a bidentate picolinate ligand
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A silver-free methodology was developed for the synthesis of unprecedented N-heterocyclic carbene ruthenium indenylidene complexes bearing a bidentate picolinate ligand. The highly stable (SIPr)(picolinate)RuCl(indenylidene) complex 4a (SIPr = 1,3- bis(2-
- Schmid, Thibault E.,Modicom, Florian,Dumas, Adrien,Borré, Etienne,Toupet, Loic,Baslé, Olivier,Mauduit, Marc
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supporting information
p. 1541 - 1546
(2016/04/09)
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- Ring-Closing and Cross-Metathesis with Artificial Metalloenzymes Created by Covalent Active Site-Directed Hybridization of a Lipase
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A series of Grubbs-type catalysts that contain lipase-inhibiting phosphoester functionalities have been synthesized and reacted with the lipase cutinase, which leads to artificial metalloenzymes for olefin metathesis. The resulting hybrids comprise the organometallic fragment that is covalently bound to the active amino acid residue of the enzyme host in an orthogonal orientation. Differences in reactivity as well as accessibility of the active site by the functionalized inhibitor became evident through variation of the anchoring motif and substituents on the N-heterocyclic carbene ligand. Such observations led to the design of a hybrid that is active in the ring-closing metathesis and the cross-metathesis of N,N-diallyl-p-toluenesulfonamide and allylbenzene, respectively, the latter being the first example of its kind in the field of artificial metalloenzymes.
- Basauri-Molina, Manuel,Verhoeven, Dide G. A.,Van Schaik, Arnoldus J.,Kleijn, Henk,Klein Gebbink, Robertus J. M.
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p. 15676 - 15685
(2015/11/03)
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- Ruthenium Olefin Metathesis Catalysts Containing Fluoride
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The reaction of the ruthenium complex cis-Caz-1 with silver fluoride affords the first example of an active olefin metathesis precatalyst containing fluoride ligands. The cis geometry of the precursor complex is key to the successful fluoride exchange rea
- Guidone, Stefano,Songis, Olivier,Falivene, Laura,Nahra, Fady,Slawin, Alexandra M. Z.,Jacobsen, Heiko,Cavallo, Luigi,Cazin, Catherine S. J.
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p. 3932 - 3939
(2015/11/27)
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- Copper-catalyzed domino homologation and cycloisomerization reactions for 3-pyrroline synthesis
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Copper bromide was found to be an efficient catalyst for a domino reaction sequence leading to 3-pyrrolines. The Cu(I)-catalyzed Crabbe reaction of propargyl sulfonamide and selective cycloisomerization of the allene intermediate were carried out using microwave irradiation conditions affording a wide range of 2-substituted- and 2,5-disubstituted-3-pyrrolines. Mechanistic studies of the reaction intermediates revealed two possible reaction pathways; both invoke the importance of vinyl copper intermediates.
- Shin, Ye Ho,Maheswara, Muchchintala,Hwang, Joon Young,Kang, Eun Joo
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supporting information
p. 2305 - 2311
(2014/04/17)
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- An attempt to provide an environmentally friendly solvent selection guide for olefin metathesis
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A range of environmentally conservative solvents was evaluated for application in olefin metathesis. Different commercially available and most frequently applied ruthenium catalysts were employed. The data obtained can be used as a guide to facilitate replacement of environmentally detrimental chlorinated or aromatic solvents with greener reaction media in order to make applications of olefin metathesis in both industry and academia more environmentally benign and sustainable processes.
- Skowerski, Krzysztof,Bialecki, Jacek,Tracz, Andrzej,Olszewski, Tomasz K.
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supporting information
p. 1125 - 1130
(2014/03/21)
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- Continuous flow olefin metathesis using a multijet oscillating disk reactor as the reaction platform
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The multijet oscillating disk (MJOD) flow reactor is a relatively new technology for continuous flow synthesis. This technology is still under investigation as an all-round platform for flow synthesis. In this article, findings are disclosed from a project where a MJOD flow reactor rig (reactor volume of ≈50 mL) was investigated as the reaction platform for ring closing metathesis and cross (self) metathesis reaction, using reaction mixture volumes down to only ≈5 mL. The Hoveyda-Grubbs second-generation catalyst was used without an inert atmosphere. The results of the flow synthesis provided excellent selectivity and high yield. For comparison purposes, the syntheses conducted in the MJOD reactor were compared with similar literature experiments performed with other flow technologies and batch conditions.
- Bjorsvik, Hans-Ren,Liguori, Lucia
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p. 1509 - 1515
(2015/02/19)
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- A six-coordinated cationic ruthenium carbyne complex with liable pyridine ligands: Synthesis, structure, catalytic investigation, and DFT study on initiation mechanism
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A novel six-coordinated high-valence cationic ruthenium carbyne complex bearing two liable pyridine ligands was prepared in high yield by the reaction of the ruthenium-based complex (IMesH2)(Cl)2(C 5H5N)2RuCHPh [IMesH2=1,3-dimesityl- 4,5-dihydroimida-zol-2-ylidene] with excess iodine as an oxidant in CH 2Cl2 at 25 °C under N2. The new ruthenium carbyne-based complex shows moderate to good catalytic activity for ring-closing metathesis reactions. Importantly, no double bond isomerization by-product was produced at elevated reaction temperatures (100 °C-137 °C) in the reaction catalyzed by the synthesized ruthenium carbyne complex. A mechanism involving the in situ conversion of the ruthenium carbyne through the addition of an iodide to the carbyne carbon was also proposed, and DFT calculations were performed to explain the initiating mechanism.
- Liu, Guiyan,Zheng, Lu,Shao, Mingbo,Zhang, Huizhu,Qiao, Weixia,Wang, Xiaojia,Liu, Bowen,Zhao, Haitao,Wang, Jianhui
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supporting information
p. 4718 - 4725
(2014/06/24)
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- Cobalt-mediated diastereoselective cross-coupling reactions between cyclic halohydrins and arylmagnesium reagents
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Cyclic TBS-protected iodohydrins (and bromohydrins) undergo a highly diastereoselective cross-coupling with various aryl- and heteroarylmagnesium reagents in the presence of THF-soluble CoCl2·2LiCl and TMEDA as a ligand leading to trans-2-arylcyclohexanol derivatives in good yields and dr up to >99:1. A range of functional groups are tolerated in the Grignard reagent (e.g., COOR, CN, CF3, SF5). The use of heterocyclic iodohydrins leads to trans-3,4-disubstituted pyrrolidines and tetrahydrofurans.
- Hammann, Jeffrey M.,Steib, Andreas K.,Knochel, Paul
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supporting information
p. 6500 - 6503
(2015/01/09)
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- Biotinylated metathesis catalysts: Synthesis and performance in ring closing metathesis
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Nine biotinylated Grubbs-Hoveyda and Grubbs-type metathesis catalysts were synthesized and evaluated in ring closing metathesis reactions of N-tosyl diallylamine and 5-hydroxy-2-vinylphenyl acrylate. Their catalytic activity in organic-and aqueous solvents was compared with the second generation Grubbs-Hoveyda catalyst. The position of the biotin-moiety on the N-heterocyclic carbene was found to critically influence the catalytic activity of the corresponding ruthenium-based catalysts. Springer Science+Business Media New York 2013.
- Kajetanowicz, Anna,Chatterjee, Anamitra,Reuter, Raphael,Ward, Thomas R.
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p. 373 - 379
(2014/06/24)
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- Synthesis, structure and catalytic study of oxygen chelated ruthenium (II) carbene complex
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New oxygen chelated ruthenium carbene complex containing carbonyl oxygen and ether oxygen has been developed. The X-ray structure of the complex showed that the carbonyl oxygen of the amide and the terminal oxygen of the benzylidene ether are both coordinated to the metal to give an octahedral structure. The catalytic activities of this new complex for olefin metathesis reactions were investigated and it exhibited excellent performances for the ring-closing metathesis (RCM) of diethyl diallymalonate at 30 °C and even at 0 °C. The initiation rate of the catalyst was higher than that for the Hoveyda catalyst ((H2IMes)(Cl)2Ru = C(H)(C6H 4-2-OiPr)) and it was also active for cross metathesis (CM).
- Liu, Guiyan,Shao, Mingbo,Zhang, Huizhu,Wang, Jianhui
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- Efficient ruthenium metathesis catalysts containing carborane ligands
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A first generation Hoveyda-Grubbs ruthenium complex with a closo-1,2-C 2B10H11 tag has been prepared. This new catalyst was tested in ring-closing metathesis (RCM) reactions and proved to be quite efficient. In addition, t
- Liu, Guiyan,Zhang, Huizhu,Zhao, Xia,Wang, Jianhui
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- Supported ruthenium-carbene catalyst on ionic magnetic nanoparticles for olefin metathesis
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The Grubbs-Hoveyda ruthenium-carbene complex has been covalently immobilized on ionic magnetic nanoparticles utilizing an imidazolium salt linker. The supported catalyst exhibited excellent catalytic activity for ring-closing metathesis (RCM) and cross-me
- Chen, Shu-Wei,Zhang, Zhi-Cheng,Ma, Miaofeng,Zhong, Chong-Min,Lee, Sang-Gi
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supporting information
p. 4969 - 4971
(2014/12/11)
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- METAL COMPLEXES, THEIR APPLICATION AND METHODS OF CARRYING OUT OF METATHESIS REACTION
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This disclosure relates to new metal complexes, such as compounds of Formula 1, and their application in olefin or alkyne metathesis and to methods of carrying out olefin metathesis reactions.
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Paragraph 00112
(2014/01/17)
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- RUTHENIUM POLYMERISATION CATALYSTS
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Cis and trans ruthenium complexes that can be used as catalysts for ring opening metathesis polymerisation (ROMP) are described. The complexes are generally square pyramidal in nature, having two anionic ligands X. Corresponding cationic complexes where one or both of the anionic ligands X are replaced by a non-co-ordinating anionic ligand are also described. Polymers such as polydicyclopentadiene (PDCPD) can be prepared using the catalysts.
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Paragraph 0091; 0092
(2014/08/19)
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- Rhodium-catalyzed asymmetric hydroarylation of 3-pyrrolines giving 3-arylpyrrolidines: Protonation as a key step
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A hydroxorhodium complex coordinated with (R)-segphos was found to catalyze the hydroarylation of 3-pyrrolines with arylboroxines under neutral conditions to give 3-arylpyrrolidines with high enantioselectivity in high yields.
- So, Chau Ming,Kume, Satoshi,Hayashi, Tamio
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p. 10990 - 10993
(2013/08/23)
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- Mixed N-heterocyclic carbene/phosphite ruthenium complexes: The effect of a bulkier NHC.
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The synthesis, characterization, and catalytic activity of two new complexes, 2a,b, featuring a sterically demanding NHC and two different phosphites are described. Complexes 2a,b display a mutually trans arrangement of the π-acidic phosphite and the strong σ-donor SIPr ligand (SIPr = N,N′-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene). The synergy between the phosphite and the NHC ligand was revealed in the RCM of challenging substrates leading to tetrasubstituted olefins where, in comparison to their phosphine-containing analogues, 2a,b allowed higher conversions of these challenging substrates.
- Urbina-Blanco, Cesar A.,Bantreil, Xavier,Wappel, Julia,Schmid, Thibault E.,Slawin, Alexandra M. Z.,Slugovc, Christian,Cazin, Catherine S. J.
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supporting information
p. 6240 - 6247
(2013/12/04)
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- Catalytic applications of recyclable silica immobilized NHC-ruthenium complexes
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A monosilylated Hoveyda-Grubbs ruthenium alkylidene has been prepared and grafted through the NHC ligand to a mesostructured silica, in refluxing toluene or at room temperature, giving two new organic-inorganic hybrid silica materials M2 and M3, respectiv
- Monge-Marcet, Amàlia,Pleixats, Roser,Catto?n, Xavier,Wong Chi Man, Michel
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p. 341 - 348
(2013/01/15)
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