Academic literature on the topic 'Grubbs-type catalyst'

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Journal articles on the topic "Grubbs-type catalyst"

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Balcar, Hynek, Naděžda Žilková, Martin Kubů, Michal Mazur, Zdeněk Bastl, and Jiří Čejka. "Ru complexes of Hoveyda–Grubbs type immobilized on lamellar zeolites: activity in olefin metathesis reactions." Beilstein Journal of Organic Chemistry 11 (November 4, 2015): 2087–96. http://dx.doi.org/10.3762/bjoc.11.225.

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Hoveyda–Grubbs type catalysts with cationic tags on NHC ligands were linker-free immobilized on the surface of lamellar zeolitic supports (MCM-22, MCM-56, MCM-36) and on mesoporous molecular sieves SBA-15. The activity of prepared hybrid catalysts was tested in olefin metathesis reactions: the activity in ring-closing metathesis of citronellene and N,N-diallyltrifluoroacetamide decreased in the order of support MCM-22 ≈ MCM-56 > SBA-15 > MCM-36; the hybrid catalyst based on SBA-15 was found the most active in self-metathesis of methyl oleate. All catalysts were reusable and exhibited low Ru leaching (<1% of Ru content). XPS analysis revealed that during immobilization ion exchange between Hoveyda–Grubbs type catalyst and zeolitic support occurred in the case of Cl− counter anion; in contrast, PF6 − counter anion underwent partial decomposition.
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Pieczykolan, Michał, Justyna Czaban-Jóźwiak, Maura Malinska, Krzysztof Woźniak, Reto Dorta, Anna Rybicka, Anna Kajetanowicz, and Karol Grela. "The Influence of Various N-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts." Molecules 25, no. 10 (May 12, 2020): 2282. http://dx.doi.org/10.3390/molecules25102282.

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A set of nitro-activated ruthenium-based Hoveyda-Grubbs type olefin metathesis catalysts bearing sterically modified N-hetero-cyclic carbene (NHC) ligands have been obtained, characterised and studied in a set of model metathesis reactions. It was found that catalysts bearing standard SIMes and SIPr ligands (4a and 4b) gave the best results in metathesis of substrates with more accessible C–C double bonds. At the same time, catalysts bearing engineered naphthyl-substituted NHC ligands (4d–e) exhibited high activity towards formation of tetrasubstituted C–C double bonds, the reaction which was traditionally Achilles’ heel of the nitro-activated Hoveyda–Grubbs catalyst.
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Vasiuta, Roman, Alexander Stockert, and Herbert Plenio. "Alternating ring-opening metathesis polymerization by Grubbs-type catalysts with N-pentiptycenyl, N-alkyl-NHC ligands." Chemical Communications 54, no. 14 (2018): 1706–9. http://dx.doi.org/10.1039/c7cc08476e.

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Mugemana, Clément, Konstantin V. Bukhryakov, Olivier Bertrand, Khanh B. Vu, Jean-François Gohy, Nikos Hadjichristidis, and Valentin O. Rodionov. "Ring opening metathesis polymerization of cyclopentene using a ruthenium catalyst confined by a branched polymer architecture." Polymer Chemistry 7, no. 17 (2016): 2923–28. http://dx.doi.org/10.1039/c6py00389c.

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A Grubbs-type Ru alkene metathesis catalyst has been covalently anchored in the core of a globular star polymer. The spatially-confined catalyst is capable of efficient ring-opening metathesis polymerization of cyclopentene, a low-strain monomer.
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Balcar, Hynek, Tushar Shinde, Naděžda Žilková, and Zdeněk Bastl. "Hoveyda–Grubbs type metathesis catalyst immobilized on mesoporous molecular sieves MCM-41 and SBA-15." Beilstein Journal of Organic Chemistry 7 (January 6, 2011): 22–28. http://dx.doi.org/10.3762/bjoc.7.4.

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A commercially available Hoveyda–Grubbs type catalyst (RC303 Zhannan Pharma) was immobilized on mesoporous molecular sieves MCM-41 and on SBA-15 by direct interaction with the sieve wall surface. The immobilized catalysts exhibited high activity and nearly 100% selectivity in several types of alkene metathesis reactions. Ru leaching was found to depend on the substrate and solvent used (the lowest leaching was found for ring-closing metathesis of 1,7-octadiene in cyclohexane – 0.04% of catalyst Ru content). Results of XPS, UV–vis and NMR spectroscopy showed that at least 76% of the Ru content was bound to the support surface non-covalently and could be removed from the catalyst by washing with THF.
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Paradiso, Veronica, Raffaele Contino, and Fabia Grisi. "NHC Ligand Effects on Ru-Catalyzed Cross-Metathesis of Renewable Materials." Catalysts 10, no. 8 (August 8, 2020): 904. http://dx.doi.org/10.3390/catal10080904.

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As petrochemical resources become increasingly scarce and expensive, much attention has been focused on renewable resources from biomass as alternative options for producing basic building blocks for chemical manufacturing. Catalytic olefin metathesis represents a powerful tool to transform biosourced structural motifs in valuable commodity, fine, and specialty chemicals. In that respect, the appropriate choice of the catalyst is the key issue of each metathesis transformation. The current study examines the influence of different N-heterocyclic carbene (NHC) ligands containing one or two N-alkyl substituents on the efficiency of Hoveyda–Grubbs-type catalysts in the cross-metathesis reaction of ethyl oleate with cis-1,4-diacetoxy-2-butene and cross-metathesis of eugenol acetate with cis-1,4-dichloro-2-butene. Interestingly, the introduction of alkyl N-substituents in the NHC ligand was revealed as beneficial for catalytic performances in the examined cross-metathesis (CM) reactions, leading to higher activity and/or selectivity than those observed in the presence of the classical, commercially available Hoveyda–Grubbs second generation catalyst (HGII).
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Kiselev, S. A., D. A. Lenev, A. A. Lyapkov, S. V. Semakin, G. Bozhenkova, F. Verpoort, and R. V. Ashirov. "Reactivity of norbornene esters in ring-opening metathesis polymerization initiated by a N-chelating Hoveyda II type catalyst." RSC Advances 6, no. 7 (2016): 5177–83. http://dx.doi.org/10.1039/c5ra25197d.

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The reactivity and activation parameters for the ROMP of eight norbornene esters in the presence of a N-chelating Hoveyda–Grubbs II type catalyst were determined. Kinetic studies prove that these parameters highly depend on the monomer structures.
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Zhang, Huan, Ying Li, Songxue Shao, Haihong Wu, and Peng Wu. "Grubbs-type catalysts immobilized on SBA-15: A novel heterogeneous catalyst for olefin metathesis." Journal of Molecular Catalysis A: Chemical 372 (June 2013): 35–43. http://dx.doi.org/10.1016/j.molcata.2013.01.034.

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Lemcoff, N., and Or Eivgi. "Turning the Light On: Recent Developments in Photoinduced Olefin Metathesis." Synthesis 50, no. 01 (September 21, 2017): 49–63. http://dx.doi.org/10.1055/s-0036-1589113.

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Olefin metathesis is one of the most important methods to form carbon–carbon double bonds and has found many applications in industry and academia. The ability to initiate the reaction using external stimulus such as light, with high spatial and temporal resolution is highly advantageous and provides creative novel opportunities in organic syntheses and material sciences. This review article covers recent advances in light-activated olefin metathesis reactions from the development of novel complexes that can be initiated photochemically to recently reported applications of photoinduced olefin metathesis, as well as the bright newly emerging field of photoredox-mediated metal-free ROMP.1 Introduction2 Light-Activated Olefin Metathesis Complexes2.1 Sulfur-Chelated Hoveyda–Grubbs-Type Complexes2.2 Nitrogen-Chelated Hoveyda–Grubbs-Type Complexes2.3 Catalyst Activation with Photoacid Generators2.4 Phototuning of Active Complexes2.5 Photoactivation of Non-Grubbs-Type Olefin Metathesis Complexes3 Photoredox-Mediated Metal-Free ROMP4 Applications of Photoinduced Olefin Metathesis4.1 Chromatic Orthogonal Olefin Metathesis4.2 UV-Filter-Assisted Olefin Metathesis4.3 Photolithographic Olefin Metathesis Polymerization5 Conclusions
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Pastva, Jakub, Jiří Čejka, Naděžda Žilková, Oto Mestek, Mojca Rangus, and Hynek Balcar. "Hoveyda–Grubbs first generation type catalyst immobilized on mesoporous molecular sieves." Journal of Molecular Catalysis A: Chemical 378 (November 2013): 184–92. http://dx.doi.org/10.1016/j.molcata.2013.06.006.

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Dissertations / Theses on the topic "Grubbs-type catalyst"

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Van, der Gryp Percy. "Separation of Grubbs-based catalysts with nanofiltration / Percy van der Gryp." Thesis, North-West University, 2008. http://hdl.handle.net/10394/2902.

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Jordaan, Margaritha. "Experimental and theoretical investigation of new Grubbs-type catalysts for the metathesis of alkenes / Margaritha Jordaan." Thesis, North-West University, 2007. http://hdl.handle.net/10394/1578.

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Motoboli, Mpho Princess. "Synthesis and modelling of imine derivatives as ligands for Grubbs type pre–catalysts / by Mpho Princess Motoboli." Thesis, North-West University, 2010. http://hdl.handle.net/10394/4633.

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The Grubbs type pre–catalysts are widely used for olefin metathesis. The pre–catalysts exhibit high activity and selectivity, but low stability and short lifetimes Salicylideneanilines (SA) are Schiff bases that can be derived from the reaction of amine derivatives with salicylaldehyde and 2–hydroxy–1–naphthaldehyde. These ligands were synthesized to improve the activity, stability and lifetime of the Grubbs first and second generation pre–catalysts. In an attempt to improve on these properties both theoretical and experimental investigations were conducted. Molecular modelling was done using Material Studio, Dmol3 (PW91/GGA/DNP) to evaluate potential imine derivative as ligands for Grubbs type pre–catalysts, for the metathesis reaction with 1–octene. Forty five ligands were chosen to investigate properties for suitable ligands. The usefulness of the HOMO energy as preliminary criteria for screening suitable ligands was investigated. The HOMO energy of possible ligands was calculated against the well defined Verpoort ligand. In this study the ligand with lower energy than that of the Verpoort's ligand was considered. Analysis of the electron density, electrostatic potential, Fukui functions, HOMOLUMO orbitals and population analysis were used to address the research problem. The second criteria included being found in literature, synthesis procedure as well as a high yield. The two most promising ligands were chosen to be synthesized. These ligands were used in the synthesis of new Grubbs 1 and 2 type pre–catalysts. The third criteria were the dissociation energy (Ru–N) for the new Grubbs type pre–catalysts for activation properties that may influence the hemilability. Furthermore molecular modelling helped to gain insight into the mechanism of the 1–octene metathesis reaction by using the Potential Energy Surface (PES) scan. Both ligands were successfully synthesized according to literature methods. The ligands were characterized by MS, IR and NMR techniques. The synthesis of substituted Grubbs 1 type pre–catalysts was unsuccessful. The substituted Grubbs 2 type pre–catalysts were obtained and characterized by MALDI–TOF and NMR techniques. The two substituted Grubbs 2 type pre–catalysts were tested for metathesis activity with 1–octene. Only one substituted pre–catalyst was active for metathesis. This catalyst was less active and selective than the Grubbs first and second generation pre–catalysts but showed an increased lifetime.
Thesis (M.Sc. (Chemistry))--North-West University, Potchefstroom Campus, 2011.
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Book chapters on the topic "Grubbs-type catalyst"

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Taber, Douglass. "Developments in Alkene Metathesis." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0024.

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Alkene metathesis has been extended to increasingly complex starting materials and products. Nitriles are good donors to coordinatively-unsaturated transition metal centers, so tend to inhibit the reaction. Ren He of Dalian University of Technology has found (Tetrahedron Lett. 2007, 48, 4203) that inclusion of the loosely-coordinating 2-methyl pyridine in the reaction enables facile cross-coupling with acrylonitrile 2. Although crosscoupling with (Z, Z)-sorbate is not efficient, Dennis P. Curran of the University of Pittsburgh has shown (Organic Lett. 2007, 9, 5) that cross-coupling with (E, Z)-sorbate 5 works well. For large scale work, he has developed a Hoveyda-type catalyst with a perfluoro tail, that is recoverable in 70% recrystallized yield from the reaction mixture. Shigefumi Kuwahara of Tohoku University has reported (Tetrahedron Lett. 2007, 48, 3163) a practical alternative for direct metathesis to deliver (E, E)-dienyl esters. Continuing the investigation of tandem Ru-catalyzed reactions, Marc L. Snapper of Boston College effected (Organic Lett. 2007, 9, 1749) metathesis with methacrolein 8a, then added Ph3P and diazoacetate, to give the diene 11. A range of common Ru catalysts worked well for this transformation. In an alternative approach to trisubstituted alkene construction, Stellios Arseniyadis and Janine Cossy of ESPCI Paris have demonstrated (Organic Lett. 2007, 9, 1695) that inclusion of Cl-catecholborane 14 allows clean cross metathesis with the lactone 13. The construction of tetrasubstituted alkenes has been more challenging. Yann Schrodi of Materia, Inc. (Organic Lett. 2007, 9, 1589) has described a catalyst 17 that is particularly effective. Complex 17 was superior to a catalyst reported (Organic Lett. 2007, 9, 1339) shortly earlier by Robert H. Grubbs of Caltech. Debendra K. Mohapatra of the National Chemical Laboratory, Pune, and Professor Grubbs, in a new approach to macrocyclic stereocontrol, have made (Tetrahedron Lett. 2007, 48, 2621) the remarkable observation that the cyclization of the bis ether 19a gave 20 in a 9:1 E / Z ratio, while cyclization of the diol 9b gave only Z - 21. Oligomer formation can often compete in such medium ring-forming reactions. Deryn E. Fogg of the University of Ottawa has raised (J. Am. Chem. Soc. 2007, 129, 1024) the cautionary (but happy!) observation that while the cyclization, for instance, of 22 proceeded efficiently to give 23, at an intermediate point in the transformation the product was more than half oligomer.
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Taber, Douglass F. "Alkene and Alkyne Metathesis: Grandisol (Goess), 8-Epihalosilane (Kouklovsky/Vincent), (+)-Chinensiolide B (Hall)." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0033.

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The cost of using Grubbs-type catalysts could be reduced dramatically if the turnover could be improved. Richard L. Pederson of Materia found (Organic Lett. 2010, 12, 984) that in MTBE at 50°C, the ring-closing metathesis of 1 proceeded to completion in 8 hours with just 500 ppm of H2 catalyst 2. Jianhui Wang of Tianjin University constructed (Angew. Chem. Int. Ed. 2010, 49, 4425) a modified H2 catalyst 5 tethered to a nitrobenzospiropyran. After the cyclization of 4 to 6 was run in CH2Cl2, the mixture was irradiated with visible light, converting 5 into its ionic form, which could be extracted with glycol/methanol, leaving little Ru residue in the cyclized product. In the dark, the catalyst reverted and could be extracted back into CH2Cl2 and reused. In a complementary approach, David W. Knight of Cardiff University found (Tetrahedron Lett. 2010, 51, 638) that the residual Ru after metathesis could be reduced to < 2 ppm simply by stirring the product with H2O2. Cyclopropenes such as 6 are readily available in enantiomerically pure form by the addition of diazoacetates to alkynes. Christophe Meyer and Janine Cossy of ESPCI ParisTech showed (Organic Lett. 2010, 12, 248) that with a Ti additive, G2 cyclized 7 to 8. Siegfried Blechert of the Technische Universität Berlin devised (Angew. Chem. Int. Ed. 2010, 49, 3972) the chiral Ru catalyst 11, which converted the prochiral 9 to 12 in high ee. Daesung Lee of the University of Illinois, Chicago, explored (J. Am. Chem. Soc. 2010, 132, 8840) the cyclization of the diyne 13 with 14 under G2 catalysis. Depending on the terminal substituent, the cyclization could be directed selectively to 15 or 16. Bran C. Goess of Furman University took advantage (J. Org. Chem. 2010, 75, 226) of alkyne ring-closing metathesis for the conversion of 17 to 18. Selective hydrogenation then delivered the boll weevil pheromone grandisol 19. Cyrille Kouklovsky and Guillaume Vincent of the Université de Paris Sud extended (J. Org. Chem. 2010, 75, 4333) ring-opening/ring-closing metathesis to the nitroso Diels-Alder adduct 20. Reduction led to 8-epihalosilane 22.
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