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Journal articles on the topic 'Grubbs-type catalyst'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

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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2

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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3

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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4

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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5

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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6

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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7

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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8

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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9

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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10

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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11

Webster, Charles Edwin. "Computational Insights into Degenerate Ethylene Exchange with a Grubbs-Type Catalyst." Journal of the American Chemical Society 129, no. 24 (June 2007): 7490–91. http://dx.doi.org/10.1021/ja071588d.

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12

Sivaramakrishna, Akella, Chinduluri Sravani, Sadhana Venkatesh, B. B. Pavankumar, Kari Vijayakrishna, Haamid R. Bhat, Prakash C. Jha, and Gregory S. Smith. "Theoretical and experimental investigations on stability and chemistry of organoiridium(iii) complexes." RSC Advances 6, no. 107 (2016): 105528–39. http://dx.doi.org/10.1039/c5ra27350a.

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Novel iridacyclononanes of the type {where L = PPh₃, PEt₃ and P(OMe)₃} have been synthesized from their bis(1-pentenyl)iridium(iii) precursors through a ring-closing metathesis reaction using Grubbs' 1st generation catalyst.

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13

Antonova, Alexandra S., Marina A. Vinokurova, Pavel A. Kumandin, Natalia L. Merkulova, Anna A. Sinelshchikova, Mikhail S. Grigoriev, Roman A. Novikov, Vladimir V. Kouznetsov, Kirill B. Polyanskii, and Fedor I. Zubkov. "Application of New Efficient Hoveyda–Grubbs Catalysts Comprising an N→Ru Coordinate Bond in a Six-Membered Ring for the Synthesis of Natural Product-Like Cyclopenta[b]furo[2,3-c]pyrroles." Molecules 25, no. 22 (November 17, 2020): 5379. http://dx.doi.org/10.3390/molecules25225379.

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The ring rearrangement metathesis (RRM) of a trans-cis diastereomer mixture of methyl 3-allyl-3a,6-epoxyisoindole-7-carboxylates derived from cheap, accessible and renewable furan-based precursors in the presence of a new class of Hoveyda–Grubbs-type catalysts, comprising an N→Ru coordinate bond in a six-membered ring, results in the difficult-to-obtain natural product-like cyclopenta[b]furo[2,3-c]pyrroles. In this process, only one diastereomer with a trans-arrangement of the 3-allyl fragment relative to the 3a,6-epoxy bridge enters into the rearrangement, while the cis-isomers polymerize almost completely under the same conditions. The tested catalysts are active in the temperature range from 60 to 120 °C at a concentration of 0.5 mol % and provide better yields of the target tricycles compared to the most popular commercially available second-generation Hoveyda–Grubbs catalyst. The diastereoselectivity of the intramolecular Diels–Alder reaction furan (IMDAF) reaction between starting 1-(furan-2-yl)but-3-en-1-amines and maleic anhydride, leading to 3a,6-epoxyisoindole-7-carboxylates, was studied as well.

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14

Balcar, Hynek, and Jiří Čejka. "SBA-15 as a Support for Effective Olefin Metathesis Catalysts." Catalysts 9, no. 9 (September 2, 2019): 743. http://dx.doi.org/10.3390/catal9090743.

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Olefin metathesis is the catalytic transformation of olefinic substrates, finding a wide range of applications in organic synthesis. The mesoporous molecular sieve Santa Barbara Amorphous (SBA-15) has proven to be an excellent support for metathesis catalysts thanks to its regular mesoporous structure, high BET area, and large pore volume. A survey of catalysts consisting of (i) molybdenum and tungsten oxides on SBA-15, and (ii) molybdenum and ruthenium organometallic complexes (Schrock and Grubbs-type carbenes) on SBA-15 is provided together with their characterization and catalytic performance in various metathesis reactions. The comparison with catalysts based on other supports demonstrates the high quality of the mesoporous molecular sieve SBA-15 as an advanced catalyst support.

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15

Hryniewicka, Agnieszka, Szymon Suchodolski, Agnieszka Wojtkielewicz, Jacek W. Morzycki, and Stanisław Witkowski. "New metathesis catalyst bearing chromanyl moieties at the N-heterocyclic carbene ligand." Beilstein Journal of Organic Chemistry 11 (December 30, 2015): 2795–804. http://dx.doi.org/10.3762/bjoc.11.300.

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The synthesis of a new type of Hoveyda–Grubbs 2nd generation catalyst bearing a modified N-heterocyclic carbene ligands is reported. The new catalyst contains an NHC ligand symmetrically substituted with chromanyl moieties. The complex was tested in model CM and RCM reactions. It showed very high activity in CM reactions with electron-deficient α,β-unsaturated compounds even at 0 °C. It was also examined in more demanding systems such as conjugated dienes and polyenes. The catalyst is stable, storable and easy to purify.

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16

Xi, Zhenxing, Hassan S. Bazzi, and John A. Gladysz. "Liquid/solid phase transfer activation of Grubbs-type alkene metathesis catalysts; application of silver salts of sulfonated polystyrene." Catal. Sci. Technol. 4, no. 12 (2014): 4178–82. http://dx.doi.org/10.1039/c4cy01021c.

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17

Zarka, M. Tobias, Oskar Nuyken, and Ralf Weberskirch. "Polymer-Bound, Amphiphilic Hoveyda-Grubbs-Type Catalyst for Ring-Closing Metathesis in Water." Macromolecular Rapid Communications 25, no. 8 (April 2004): 858–62. http://dx.doi.org/10.1002/marc.200300297.

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18

Simal, François, Dominique Jan, Lionel Delaude, Albert Demonceau, Marie-Rose Spirlet, and Alfred F. Noels. "Evaluation of ruthenium-based complexes for the controlled radical polymerization of vinyl monomers." Canadian Journal of Chemistry 79, no. 5-6 (May 1, 2001): 529–35. http://dx.doi.org/10.1139/v00-206.

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New complexes of the type RuCl2(p-cymene)L where the ligand L is either a phosphine or a stable triazolinylidene carbene have been tested and compared to the Grubbs' benzylidene complex RuCl2(=CHPh)(PCy3)2 as catalyst precursors for the controlled atom transfer radical polymerization (ATRP) of methyl methacrylate and of various para-substituted styrenes. Kinetic data and Hammett ρ constants are reported, as well as the X-ray structure of the ortho-metallated triazolinylidene-ruthenium(II) complex RuCl(p-cymene)[1,2-phenylene[3,4-diphenyl-1H-1,2,4-triazol-1-yl-5(4H)-ylidene]].Key words: ruthenium, carbene, chelate complex, homogeneous catalysis, atom transfer radical polymerization.

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19

Balcar, Hynek, Naděžda Žilková, Martin Kubů, Miroslav Polášek, and Jiří Zedník. "Metathesis of cardanol over ammonium tagged Hoveyda-Grubbs type catalyst supported on SBA-15." Catalysis Today 304 (April 2018): 127–34. http://dx.doi.org/10.1016/j.cattod.2017.09.049.

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20

Tiso, Till, Daniel F. Sauer, Klaus Beckerle, Christian C. Blesken, Jun Okuda, and Lars M. Blank. "A Combined Bio-Chemical Synthesis Route for 1-Octene Sheds Light on Rhamnolipid Structure." Catalysts 10, no. 8 (August 4, 2020): 874. http://dx.doi.org/10.3390/catal10080874.

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Here we report a chemoenzymatic approach to synthesize 1-octene from carbohydrates via ethenolysis of rhamnolipids. Rhamnolipids synthesized by P. putida contain a double bond between carbon five and six, which is experimentally confirmed via olefin cross metathesis. Utilizing these lipids in the ethenolysis catalyzed by a Grubbs−Hoveyda-type catalyst selectively generates 1-octene and with good conversions. This study shows the potential of chemoenzymatic approaches to produce compounds for the chemical industry from renewable resources.

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21

Shinde, Tushar, Naděžda Žilková, Vladimíra Hanková, and Hynek Balcar. "Hoveyda–Grubbs type metathesis catalyst immobilized on mesoporous molecular sieves—The influence of pore size on the catalyst activity." Catalysis Today 179, no. 1 (January 2012): 123–29. http://dx.doi.org/10.1016/j.cattod.2011.06.012.

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22

Grimm, Alexander R., Daniel F. Sauer, Tayebeh Mirzaei Garakani, Kristin Rübsam, Tino Polen, Mehdi D. Davari, Felix Jakob, Johannes Schiffels, Jun Okuda, and Ulrich Schwaneberg. "Anchor Peptide-Mediated Surface Immobilization of a Grubbs-Hoveyda-Type Catalyst for Ring-Opening Metathesis Polymerization." Bioconjugate Chemistry 30, no. 3 (January 15, 2019): 714–20. http://dx.doi.org/10.1021/acs.bioconjchem.8b00874.

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23

Brodzka, Anna, Dominik Koszelewski, and Ryszard Ostaszewski. "Dual Activity of Grubbs-Type Catalyst in the Transvinylation of Carboxylic Acids and Ring-Closing Metathesis Reactions." Journal of Organic Chemistry 85, no. 23 (November 16, 2020): 15305–13. http://dx.doi.org/10.1021/acs.joc.0c02135.

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24

Koy, Maximilian, Hagen J. Altmann, Benjamin Autenrieth, Wolfgang Frey, and Michael R. Buchmeiser. "Grubbs–Hoveyda type catalysts bearing a dicationic N-heterocyclic carbene for biphasic olefin metathesis reactions in ionic liquids." Beilstein Journal of Organic Chemistry 11 (September 15, 2015): 1632–38. http://dx.doi.org/10.3762/bjoc.11.178.

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The novel dicationic metathesis catalyst [(RuCl2(H2ITapMe2)(=CH–2-(2-PrO)-C6H4))2+ (OTf−)2] (Ru-2, H2ITapMe2 = 1,3-bis(2’,6’-dimethyl-4’-trimethylammoniumphenyl)-4,5-dihydroimidazol-2-ylidene, OTf− = CF3SO3 −) based on a dicationic N-heterocyclic carbene (NHC) ligand was prepared. The reactivity was tested in ring opening metathesis polymerization (ROMP) under biphasic conditions using a nonpolar organic solvent (toluene) and the ionic liquid (IL) 1-butyl-2,3-dimethylimidazolium tetrafluoroborate [BDMIM+][BF4 −]. The structure of Ru-2 was confirmed by single crystal X-ray analysis.

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25

Lloyd-Jones, Guy C, Alan J Robinson, Laurent Lefort, and Johannes G de Vries. "A Simple and Effective Co-Catalyst for Ring-Closing Enyne Metathesis Using Grubbs I type Catalysts: A Practical Alternative to “Mori’s Conditions”." Chemistry - A European Journal 16, no. 31 (July 21, 2010): 9449–52. http://dx.doi.org/10.1002/chem.201001510.

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26

Núñez-Zarur, Francisco, Xavier Solans-Monfort, Roser Pleixats, Luis Rodríguez-Santiago, and Mariona Sodupe. "DFT Study on the Recovery of Hoveyda-Grubbs-Type Catalyst Precursors in Enyne and Diene Ring-Closing Metathesis." Chemistry - A European Journal 19, no. 43 (September 20, 2013): 14553–65. http://dx.doi.org/10.1002/chem.201301898.

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27

Michalek, Florian, Daniel Mädge, Jürgen Rühe, and Willi Bannwarth. "The activity of covalently immobilized Grubbs–Hoveyda type catalyst is highly dependent on the nature of the support material." Journal of Organometallic Chemistry 691, no. 24-25 (December 2006): 5172–80. http://dx.doi.org/10.1016/j.jorganchem.2006.06.030.

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28

Ashirov, R. V., D. I. Zemlyakov, A. A. Lyapkov, and S. A. Kiselev. "Kinetics of the metathesis polymerization of 5,6-Di(methoxycarbonyl)bicyclo[2.2.1]hept-2-enes on an original Hoveyda-Grubbs II type catalyst." Kinetics and Catalysis 54, no. 4 (July 2013): 469–74. http://dx.doi.org/10.1134/s0023158413040010.

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29

Hansen, Sven Michael, Frank Rominger, Markus Metz, and Peter Hofmann. "The First Grubbs-Type Metathesis Catalyst withcis Stereochemistry: Synthesis of [(η2-dtbpm)Cl2Ru=CH−CH=CMe2] from a Novel, Coordinatively Unsaturated Dinuclear Ruthenium Dihydride." Chemistry - A European Journal 5, no. 2 (February 1, 1999): 557–66. http://dx.doi.org/10.1002/(sici)1521-3765(19990201)5:2<557::aid-chem557>3.0.co;2-a.

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30

Song, Wei, Yadi Li, Xunhu Liu, Zongyi Xu, Jianhua Wu, and Liang Ding. "Functional Block Copolymers Carrying One Double-Stranded Ladderphane and One Single-Stranded Block in a Facile Metathesis Cyclopolymerization Procedure." International Journal of Molecular Sciences 20, no. 20 (October 18, 2019): 5166. http://dx.doi.org/10.3390/ijms20205166.

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In order to improve the poor film-forming ability of polymeric ladderphane, di-block copolymers containing perylene diimide (PDI)-linked double-stranded poly(1,6–heptadiyne) ladderphane and branched alkyl side chains modified single-stranded poly(1,6–heptadiyne) were synthesized by metathesis cyclopolymerization (MCP) using Grubbs third-generation catalyst (Ru–III) in tetrahydrofuran solvent. The first block containing the ladderphane structure leads to higher thermal-stability, wider UV–vis absorption, lower LUMO level and ladderphane-induced rigidity and poor film-forming ability. The second block containing long alkyl chains is crucial for the guarantee of excellent film-forming ability. By comparing the effect of ladderphane structure on the resulted copolymers, single-stranded poly(1,6–heptadiyne) derivatives with PDI pedant were also processed. The structures of copolymers were proved by 1H NMR and gel permeation chromatography, electrochemical, photophysical, and thermal-stability performance were achieved by cyclic voltammetry (CV), UV-visible spectroscopy and thermogravimetric analysis (TGA) measurements. According to the experiment results, both copolymers possessed outstanding film-forming ability, which cannot be realized by small PDI molecules and oligomers. And they can serve as a superior candidate as for n-type materials, especially for their relatively wide range of light absorption (λ = 200~800 nm), and lower LUMO level (−4.3 and −4.0 eV).

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31

Yang, Sheng-Yong, Miklos J. Szabo, Artur Michalak, Thomas Weiss, Warren E. Piers, Richard F. Jordan, and Tom Ziegler. "The Exploration of Neutral Azoligand-Based Grubbs Type Palladium(II) Complex as Potential Catalyst for the Copolymerization of Ethylene with Acrylonitrile: A Theoretical Study Based on Density Functional Theory." Organometallics 24, no. 6 (March 2005): 1242–51. http://dx.doi.org/10.1021/om049015m.

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32

Matsuo, Takashi. "Functionalization of Ruthenium Olefin-Metathesis Catalysts for Interdisciplinary Studies in Chemistry and Biology." Catalysts 11, no. 3 (March 10, 2021): 359. http://dx.doi.org/10.3390/catal11030359.

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Hoveyda–Grubbs-type complexes, ruthenium catalysts for olefin metathesis, have gained increased interest as a research target in the interdisciplinary research fields of chemistry and biology because of their high functional group selectivity in olefin metathesis reactions and stabilities in aqueous media. This review article introduces the application of designed Hoveyda–Grubbs-type complexes for bio-relevant studies including the construction of hybrid olefin metathesis biocatalysts and the development of in-vivo olefin metathesis reactions. As a noticeable issue in the employment of Hoveyda–Grubbs-type complexes in aqueous media, the influence of water on the catalytic activities of the complexes and strategies to overcome the problems resulting from the water effects are also discussed. In connection to the structural effects of protein structures on the reactivities of Hoveyda–Grubbs-type complexes included in the protein, the regulation of metathesis activities through second-coordination sphere effect is presented, demonstrating that the reactivities of Hoveyda–Grubbs-type complexes are controllable by the structural modification of the complexes at outer-sphere parts. Finally, as a new-type reaction based on the ruthenium-olefin specific interaction, a recent finding on the ruthenium complex transfer reaction between Hoveyda–Grubbs-type complexes and biomolecules is introduced.

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33

Kobyzhcha, N. I., V. S. Pyliavskyi, V. V. Sukhoveev, and V. I. Kashkovskyi. "Derivatives of pyrimidine-2,4,6-triones as components of additives to increase the lubricating properties of motor fuels." Catalysis and petrochemistry, no. 30 (2020): 97–101. http://dx.doi.org/10.15407/kataliz2020.30.097.

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One of the important tasks of modern petrochemistry is the development of new additives that can improve the performance of motor fuels. With the expansion of the number of automotive and agricultural machinery and increasing its technical level, the demand for a wider range of petroleum products is increasing and, as well, the requirements for their quality are increasing. As the environmental and operational requirements for motor fuels are constantly increasing, it is necessary to find new, more efficient additives. The paper describes the synthesis of spirocyclic pyrimidine-2,4,6-trionеs by ring-closing metathesis reactions (RCM). This type of transformation is actively used in petrochemical and organic syntheses and allows to obtain compounds that are difficult to synthesize by conventional methods of organic chemistry. RCM conversion was performed using a Grubbs-Hoveyda catalyst in an amount of 5 mol. %. The compounds formed during the reaction were investigated as additives to motor fuels. Studies of the effect of synthesized spiropyrimidine-2,4,6-trione derivatives as additives on the tribological characteristics of ethanol and diesel fuel were evaluated on a four-ball tribometer in terms of critical load. At least three experiments were performed at each load. The error of the experiment was less than 5%. It was found that substances 2c and 2b increase the lubricating properties of ethanol - the critical load to the fuel burr when adding the synthesized compounds increased by 25%. Spiropyrimidine-2,4,6-trione 2b also had a positive effect on the lubricity of diesel fuel and had the effect of increasing the load to burr by 12% at a concentration of 0.032%. Thus, derivatives of spiropyrimidine-2,4,6-triones have proven to be promising compounds for the manufacture of motor fuels.

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34

Pijnenburg, Niels J. M., Eder Tomás-Mendivil, Kimberley E. Mayland, Henk Kleijn, Martin Lutz, Anthony L. Spek, Gerard van Koten, and Robertus J. M. Klein Gebbink. "Monomeric and dendritic second generation Grubbs- and Hoveyda–Grubbs-type catalysts for olefin metathesis." Inorganica Chimica Acta 409 (January 2014): 163–73. http://dx.doi.org/10.1016/j.ica.2013.06.018.

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35

Sauer, Daniel F., Johannes Schiffels, Takashi Hayashi, Ulrich Schwaneberg, and Jun Okuda. "Olefin metathesis catalysts embedded in β-barrel proteins: creating artificial metalloproteins for olefin metathesis." Beilstein Journal of Organic Chemistry 14 (November 19, 2018): 2861–71. http://dx.doi.org/10.3762/bjoc.14.265.

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This review summarizes the recent progress of Grubbs–Hoveyda (GH) type olefin metathesis catalysts incorporated into the robust fold of β-barrel proteins. Anchoring strategies are discussed and challenges and opportunities in this emerging field are shown from simple small-molecule transformations over ring-opening metathesis polymerizations to in vivo olefin metathesis.

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36

Wappel, Julia, Roland C. Fischer, Luigi Cavallo, Christian Slugovc, and Albert Poater. "Simple activation by acid of latent Ru-NHC-based metathesis initiators bearing 8-quinolinolate co-ligands." Beilstein Journal of Organic Chemistry 12 (January 28, 2016): 154–65. http://dx.doi.org/10.3762/bjoc.12.17.

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A straightforward synthesis utilizing the ring-opening metathesis polymerization (ROMP) reaction is described for acid-triggered N,O-chelating ruthenium-based pre-catalysts bearing one or two 8-quinolinolate ligands. The innovative pre-catalysts were tested regarding their behavior in ROMP and especially for their use in the synthesis of poly(dicyclopentadiene) (pDCPD). Bearing either the common phosphine leaving ligand in the first and second Grubbs olefin metathesis catalysts, or the Ru–O bond cleavage for the next Hoveyda-type catalysts, this work is a step forward towards the control of polymer functionalization and living or switchable polymerizations.

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37

Jatmika, Catur, Kenta Goshima, Kazumo Wakabayashi, Naoki Akiyama, Shun Hirota, and Takashi Matsuo. "Second-coordination sphere effects on the reactivities of Hoveyda–Grubbs-type catalysts: a ligand exchange study using phenolic moiety-functionalized ligands." Dalton Transactions 49, no. 33 (2020): 11618–27. http://dx.doi.org/10.1039/d0dt02353a.

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38

van der Gryp, Percy, Anro Barnard, Jean-Pierre Cronje, Dennis de Vlieger, Sanette Marx, and Hermanus C. M. Vosloo. "Separation of different metathesis Grubbs-type catalysts using organic solvent nanofiltration." Journal of Membrane Science 353, no. 1-2 (May 1, 2010): 70–77. http://dx.doi.org/10.1016/j.memsci.2010.02.032.

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39

Schoeps, Dirk, Kristian Buhr, Marga Dijkstra, Katrin Ebert, and Herbert Plenio. "Batchwise and Continuous Organophilic Nanofiltration of Grubbs-Type Olefin Metathesis Catalysts." Chemistry - A European Journal 15, no. 12 (March 9, 2009): 2960–65. http://dx.doi.org/10.1002/chem.200802153.

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40

Barbasiewicz, Michał, Michał Michalak, and Karol Grela. "A New Family of Halogen-Chelated Hoveyda-Grubbs-Type Metathesis Catalysts." Chemistry - A European Journal 18, no. 45 (October 2, 2012): 14237–41. http://dx.doi.org/10.1002/chem.201202817.

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41

Krause, Jens O, Said Lubbad, Oskar Nuyken, and Michael R Buchmeiser. "Monolith- and Silica-Supported Carboxylate-Based Grubbs–Herrmann-Type Metathesis Catalysts." Advanced Synthesis & Catalysis 345, no. 8 (August 2003): 996–1004. http://dx.doi.org/10.1002/adsc.200303037.

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42

Dinger, Maarten B., Piotr Nieczypor, and Johannes C. Mol. "Adamantyl-SubstitutedN-Heterocyclic Carbene Ligands in Second-Generation Grubbs-Type Metathesis Catalysts." Organometallics 22, no. 25 (December 2003): 5291–96. http://dx.doi.org/10.1021/om034062k.

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43

Cheong, Jian Liang, Daniel Wong, Song-Gil Lee, Jaehong Lim, and Su Seong Lee. "Role of grafted alkoxybenzylidene ligand in silica-supported Hoveyda–Grubbs-type catalysts." Chemical Communications 51, no. 6 (2015): 1042–45. http://dx.doi.org/10.1039/c4cc08627a.

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44

Buchmeiser, Michael, and Emily Anderson. "‘Pseudo-halide’ Derivatives of Grubbs- and Schrock-Type Catalysts for Olefin Metathesis." Synlett 2012, no. 02 (December 22, 2011): 185–207. http://dx.doi.org/10.1055/s-0031-1290120.

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45

Ullah, Mohammad Shahid, Sadia Afrin Chhanda, and Shinichi Itsuno. "ADMET Polymerization of Dimeric Cinchona Squaramides for the Preparation of a Highly Enantioselective Polymeric Organocatalyst." Catalysts 10, no. 5 (May 25, 2020): 591. http://dx.doi.org/10.3390/catal10050591.

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Under the acyclic diene metathesis (ADMET) reaction condition, the C3-vinyl groups of cinchona alkaloids readily react with each other to form a C-C bond. A novel type of cinchona alkaloid polymers was synthesized from dimeric cinchona squaramides using the Hoveyda-Grubbs’ second-generation catalysts (HG2) by means of ADMET reaction. The chiral polymers, containing cinchona squaramide moieties in their main chains, were subsequently employed as catalysts for the enantioselective Michael reaction to give the corresponding chiral adducts in high yields with excellent enantioselectivity and diastereoselectivity. Both enantiomers from the asymmetric Michael reaction were distinctively prepared while using the polymeric catalysts, possessing pseudoenantiomeric structures. The catalysts were readily recovered from the reaction mixture and recycled several times due to the insolubility of the cinchona-based squaramide polymers.

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46

Peterson, Gregory I., Sanghee Yang, and Tae-Lim Choi. "Synthesis of Functional Polyacetylenes via Cyclopolymerization of Diyne Monomers with Grubbs-type Catalysts." Accounts of Chemical Research 52, no. 4 (January 28, 2019): 994–1005. http://dx.doi.org/10.1021/acs.accounts.8b00594.

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47

Kajetanowicz, Anna, Justyna Czaban, G. Rajesh Krishnan, Maura Malińska, Krzysztof Woźniak, Humera Siddique, Ludmila G. Peeva, Andrew G. Livingston, and Karol Grela. "Batchwise and Continuous Nanofiltration of POSS-Tagged Grubbs-Hoveyda-Type Olefin Metathesis Catalysts." ChemSusChem 6, no. 1 (October 19, 2012): 182–92. http://dx.doi.org/10.1002/cssc.201200466.

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48

Borré, Etienne, Frederic Caijo, Christophe Crévisy, and Marc Mauduit. "New library of aminosulfonyl-tagged Hoveyda–Grubbs type complexes: Synthesis, kinetic studies and activity in olefin metathesis transformations." Beilstein Journal of Organic Chemistry 6 (December 6, 2010): 1159–66. http://dx.doi.org/10.3762/bjoc.6.132.

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Seven novel Hoveyda–Grubbs precatalysts bearing an aminosulfonyl function are reported. Kinetic studies indicate an activity enhancement compared to Hoveyda’s precatalyst. A selection of these catalysts was investigated with various substrates in ring-closing metathesis of dienes or enynes and cross metathesis. The results demonstrate that these catalysts show a good tolerance to various chemical functions.

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Małecki, Paweł, Katarzyna Gajda, Osman Ablialimov, Maura Malińska, Roman Gajda, Krzysztof Woźniak, Anna Kajetanowicz, and Karol Grela. "Hoveyda–Grubbs-Type Precatalysts with UnsymmetricalN-Heterocyclic Carbenes as Effective Catalysts in Olefin Metathesis." Organometallics 36, no. 11 (May 25, 2017): 2153–66. http://dx.doi.org/10.1021/acs.organomet.7b00211.

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Vieille-Petit, Ludovic, Xinjun Luan, Michele Gatti, Sascha Blumentritt, Anthony Linden, Hervé Clavier, Steven P. Nolan, and Reto Dorta. "Improving Grubbs’ II type ruthenium catalysts by appropriately modifying the N-heterocyclic carbene ligand." Chemical Communications, no. 25 (2009): 3783. http://dx.doi.org/10.1039/b904634h.

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