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Journal articles on the topic 'Supported organocatalysis'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 February 2022

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1

Sánchez-Antonio, Omar, Kevin A. Romero-Sedglach, Erika C. Vázquez-Orta, and Eusebio Juaristi. "New Mesoporous Silica-Supported Organocatalysts Based on (2S)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction." Molecules 25, no. 19 (2020): 4532. http://dx.doi.org/10.3390/molecules25194532.

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Novel organocatalytic systems based on the recently developed (S)-proline derivative (2S)-[5-(benzylthio)-4-phenyl-(1,2,4-triazol)-3-yl]-pyrrolidine supported on mesoporous silica were prepared and their efficiency was assessed in the asymmetric aldol reaction. These materials were fully characterized by FT-IR, MS, XRD, and SEM microscopy, gathering relevant information regarding composition, morphology, and organocatalyst distribution in the doped silica. Careful optimization of the reaction conditions required for their application as catalysts in asymmetric aldol reactions between ketones a

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2

Zhang, Long, Lingyun Cui, Sanzhong Luo, and Jin-Pei Cheng. "ChemInform Abstract: Supported Asymmetric Organocatalysis." ChemInform 44, no. 18 (2013): no. http://dx.doi.org/10.1002/chin.201318230.

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3

Huang, Yibo, and Wei Zhang. "ChemInform Abstract: Magnetic Nanoparticle-Supported Organocatalysis." ChemInform 45, no. 45 (2014): no. http://dx.doi.org/10.1002/chin.201445276.

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4

Ferré, M., R. Pleixats, M. Wong Chi Man, and X. Cattoën. "Recyclable organocatalysts based on hybrid silicas." Green Chemistry 18, no. 4 (2016): 881–922. http://dx.doi.org/10.1039/c5gc02579f.

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5

Rodríguez-Escrich, Carles, and Miquel A. Pericàs. "Organocatalysis on Tap: Enantioselective Continuous Flow Processes Mediated by Solid-Supported Chiral Organocatalysts." European Journal of Organic Chemistry 2015, no. 6 (2015): 1173–88. http://dx.doi.org/10.1002/ejoc.201403042.

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6

Upadhyay, Praveenkumar, and Vivek Srivastava. "Proline Based Organocatalysis: Supported and Unsupported Approach." Current Organocatalysis 3, no. 3 (2016): 243–69. http://dx.doi.org/10.2174/2213337202666150812230640.

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7

Rodriguez-Escrich, Carles, and Miquel A. Pericas. "ChemInform Abstract: Organocatalysis on Tap: Enantioselective Continuous Flow Processes Mediated by Solid-Supported Chiral Organocatalysts." ChemInform 46, no. 16 (2015): no. http://dx.doi.org/10.1002/chin.201516338.

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8

Wang, Chang An, Yuan Zhang, Jiao Yi Shi, and Wei Wang. "A Self-Supported Polymeric MacMillan Catalyst for Homogeneous Organocatalysis and Heterogeneous Recycling." Chemistry - An Asian Journal 8, no. 6 (2013): 1110–14. http://dx.doi.org/10.1002/asia.201300152.

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9

Bulman Page, Philip C., Andrew Mace, Damien Arquier, et al. "Towards heterogeneous organocatalysis: chiral iminium cations supported on porous materials for enantioselective alkene epoxidation." Catalysis Science & Technology 3, no. 9 (2013): 2330. http://dx.doi.org/10.1039/c3cy00352c.

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10

Kisszékelyi, Péter, Sándor Nagy, Zsuzsanna Fehér, Péter Huszthy, and József Kupai. "Membrane-Supported Recovery of Homogeneous Organocatalysts: A Review." Chemistry 2, no. 3 (2020): 742–58. http://dx.doi.org/10.3390/chemistry2030048.

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As catalysis plays a significant role in the development of economical and sustainable chemical processes, increased attention is paid to the recovery and reuse of high-value catalysts. Although homogeneous catalysts are usually more active and selective than the heterogeneous ones, both catalyst recycling and product separation pose a challenge for developing industrially feasible methods. In this respect, membrane-supported recovery of organocatalysts represents a particularly useful tool and a valid option for organocatalytic asymmetric synthesis. However, catalyst leaching/degradation and

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11

Benmaati, Aouicha, Hadjira Zahmani, Salih Hacini, et al. "From Simple Cyclic 1,3-Ketoamides to Complex Spirolactams by Supported Heterogeneous Organocatalysis with PS-BEMP." Synthesis 48, no. 19 (2016): 3217–31. http://dx.doi.org/10.1055/s-0035-1561485.

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The reaction between cyclic 1,3-ketoamides and Michael acceptors in the presence of a catalytic amount of a polymer-supported organobase PS-BEMP has been developed for a direct access to spirocyclic 1,3-ketolactams through a domino Michael addition/hemiacetalization sequence. The products could be isolated in high chemical yields and purities after simple filtration, and the catalyst could be re-used without any re-activation. These spirolactams, containing a hemiaminal moiety, may be viewed as precursors of N-acyliminium intermediates upon Lewis acid activation, which allowed various subseque

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12

Liu, Hailing. "Nucleophilic polymer-supported tertiaryphosphine organocatalysis: [3+2] annulation reaction of alkyl 2-butynoates with activated alkenes." Chemical Research in Chinese Universities 30, no. 4 (2014): 593–95. http://dx.doi.org/10.1007/s40242-014-4063-5.

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13

Kim, Hyun Sook, Yu-Mi Song, Jin Seok Choi, Jung Woon Yang, and Hogyu Han. "Heterogeneous organocatalysis for the asymmetric desymmetrization of meso-cyclic anhydrides using silica gel-supported bis-cinchona alkaloids." Tetrahedron 60, no. 52 (2004): 12051–57. http://dx.doi.org/10.1016/j.tet.2004.10.046.

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14

Krishnan, G. Rajesh, and Krishnapillai Sreekumar. "First Example of Organocatalysis by Polystyrene-Supported PAMAM Dendrimers: Highly Efficient and Reusable Catalyst for Knoevenagel Condensations." European Journal of Organic Chemistry 2008, no. 28 (2008): 4763–68. http://dx.doi.org/10.1002/ejoc.200800516.

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15

Ötvös, Sándor B., István M. Mándity, and Ferenc Fülöp. "Highly Efficient 1,4-Addition of Aldehydes to Nitroolefins: Organocatalysis in Continuous Flow by Solid-Supported Peptidic Catalysts." ChemSusChem 5, no. 2 (2012): 266–69. http://dx.doi.org/10.1002/cssc.201100332.

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16

Pecchioli, Tommaso, Manoj Kumar Muthyala, Rainer Haag, and Mathias Christmann. "Multivalent polyglycerol supported imidazolidin-4-one organocatalysts for enantioselective Friedel–Crafts alkylations." Beilstein Journal of Organic Chemistry 11 (May 12, 2015): 730–38. http://dx.doi.org/10.3762/bjoc.11.83.

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The first immobilization of a MacMillan’s first generation organocatalyst onto dendritic support is described. A modified tyrosine-based imidazolidin-4-one was grafted to a soluble high-loading hyperbranched polyglycerol via a copper-catalyzed alkyne–azide cycloaddition (CuAAC) reaction and readily purified by dialysis. The efficiency of differently functionalized multivalent organocatalysts 4a–c was tested in the asymmetric Friedel–Crafts alkylation of N-methylpyrrole with α,β-unsaturated aldehydes. A variety of substituted enals was investigated to explore the activity of the catalytic syste

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17

Coupillaud, Paul, Julien Pinaud, Nicolas Guidolin, et al. "Poly(ionic liquid)s based on imidazolium hydrogen carbonate monomer units as recyclable polymer-supported N -heterocyclic carbenes: Use in organocatalysis." Journal of Polymer Science Part A: Polymer Chemistry 51, no. 21 (2013): 4530–40. http://dx.doi.org/10.1002/pola.26869.

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18

Chakrabarty, Kuheli, Atanu Basak, Animesh Ghosh, and Gourab Kanti Das. "Ionic liquid supported acid additive stabilizes the transition structure of organocatalytic asymmetric direct aldol reaction by proton donation: A quantum mechanical study." Journal of Theoretical and Computational Chemistry 15, no. 06 (2016): 1650049. http://dx.doi.org/10.1142/s0219633616500498.

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ONIOM studies were performed on the transition structure (TS) of organocatalytic direct aldol reaction by using ionic liquid supported benzoic acid (ILS-PhCO2H) as an additive. Results obtained from this computation suggest direct involvement of ILS-PhCO2H in the TS as a proton donor. It has also come out from the present study that, the counter ion of the ILS-acid additive may also play significant role to maintain the proper TS geometry by holding the organocatalyst and the acid additive close together during the course of reaction.

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19

Yang, Yun-Chin, and David E. Bergbreiter. "Soluble polymer-supported organocatalysts." Pure and Applied Chemistry 85, no. 3 (2012): 493–509. http://dx.doi.org/10.1351/pac-con-12-05-03.

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Organocatalysts have been extensively studied for the past few decades as alternatives to transition-metal catalysts. Immobilizing organocatalysts on polymer supports allows easy recovery and simple product purification after a reaction. Select examples of recent reports that describe the potential advantages of using soluble polymers to prepare soluble polymer-supported organocatalysts useful in organic synthesis are reviewed.

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20

Liu, Hai-Ling, Huan-Feng Jiang, Lin Xu та Hai-Ying Zhan. "Solvent-free heterogeneous organocatalysis: stereoselective isomerization of α,β-ynones to (E,E)-α,β-γ,δ-dienones catalyzed by polymer-supported tertiaryphosphines". Tetrahedron Letters 48, № 47 (2007): 8371–75. http://dx.doi.org/10.1016/j.tetlet.2007.09.093.

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21

Zhang, Richeng, Guohui Yin, Yang Li, Xilong Yan, and Ligong Chen. "Resin-immobilized pyrrolidine-based chiral organocatalysts for asymmetric Michael additions of ketones and aldehydes to nitroolefins." RSC Advances 5, no. 5 (2015): 3461–64. http://dx.doi.org/10.1039/c4ra10684a.

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22

Sagamanova, Irina K., Sonia Sayalero, Sheila Martínez-Arranz, Ana C. Albéniz, and Miquel A. Pericàs. "Asymmetric organocatalysts supported on vinyl addition polynorbornenes for work in aqueous media." Catalysis Science & Technology 5, no. 2 (2015): 754–64. http://dx.doi.org/10.1039/c4cy01344a.

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23

Yang, Yun-Chin, and David E. Bergbreiter. "ChemInform Abstract: Soluble Polymer-Supported Organocatalysts." ChemInform 44, no. 21 (2013): no. http://dx.doi.org/10.1002/chin.201321249.

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24

Akiyama, Midori, Kengo Akagawa, Hidetake Seino, and Kazuaki Kudo. "Peptide-catalyzed kinetic resolution of planar-chiral metallocenes." Chem. Commun. 50, no. 58 (2014): 7893–96. http://dx.doi.org/10.1039/c4cc03266g.

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25

Lanzilotto, Valeria, Cesare Grazioli, Matus Stredansky, et al. "Tailoring surface-supported water–melamine complexes by cooperative H-bonding interactions." Nanoscale Advances 3, no. 8 (2021): 2359–65. http://dx.doi.org/10.1039/d0na01034k.

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26

Wan, Jingwei, Lu ding, Tao Wu, Xuebing Ma, and Qian Tang. "Facile one-pot fabrication of magnetic nanoparticles (MNPs)-supported organocatalysts using phosphonate as an anchor point through direct co-precipitation method." RSC Adv. 4, no. 72 (2014): 38323–33. http://dx.doi.org/10.1039/c4ra04720f.

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Novel MNP-supported organocatalysts were prepared by one-pot co-precipitation and surface modification using phosphonate as an anchor point, and exhibited excellent performance in aqueous asymmetric aldol reactions.

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27

Franconetti, Antonio, and Gonzalo de Gonzalo. "Recent Developments on Supported Hydrogen-bond Organocatalysts." ChemCatChem 10, no. 24 (2018): 5554–72. http://dx.doi.org/10.1002/cctc.201801459.

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28

Großeheilmann, Julia, Thomas Fahrenwaldt, and Udo Kragl. "Organic Solvent Nanofiltration-Supported Purification of Organocatalysts." ChemCatChem 8, no. 2 (2015): 322–25. http://dx.doi.org/10.1002/cctc.201500902.

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29

Gupta, Ajay, Ramen Jamatia, and Amarta Kumar Pal. "Ferrite-supported glutathione: an efficient, green nano-organocatalyst for the synthesis of pyran derivatives." New Journal of Chemistry 39, no. 7 (2015): 5636–42. http://dx.doi.org/10.1039/c5nj00657k.

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30

Wang, Song, Pingwei Liu, Wen-Jun Wang, Zhiguo Zhang, and Bo-Geng Li. "Hyperbranched polyethylene-supported l-proline: a highly selective and recyclable organocatalyst for asymmetric aldol reactions." Catalysis Science & Technology 5, no. 7 (2015): 3798–805. http://dx.doi.org/10.1039/c5cy00250h.

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31

Jose, T., S. Cañellas, M. A. Pericàs, and A. W. Kleij. "Polystyrene-supported bifunctional resorcinarenes as cheap, metal-free and recyclable catalysts for epoxide/CO2 coupling reactions." Green Chemistry 19, no. 22 (2017): 5488–93. http://dx.doi.org/10.1039/c7gc02856c.

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32

Ge, Xin, Chao Qian, Xiaoming Ye, and Xinzhi Chen. "Asymmetric reduction of imines with trichlorosilane catalyzed by valine-derived formamide immobilized onto magnetic nano-Fe3O4." RSC Advances 5, no. 80 (2015): 65402–7. http://dx.doi.org/10.1039/c5ra08516k.

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Magnetic nano-Fe<sub>3</sub>O<sub>4</sub>-supported organocatalysts were synthesized by anchoring valine-derived formamide onto the surface of Fe<sub>3</sub>O<sub>4</sub> magnetic nanoparticles, which were applied in the asymmetric reduction of imines with trichlorosilane.

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33

Osorio-Planes, Laura, Carles Rodríguez-Escrich, and Miquel A. Pericàs. "Removing the superfluous: a supported squaramide catalyst with a minimalistic linker applied to the enantioselective flow synthesis of pyranonaphthoquinones." Catalysis Science & Technology 6, no. 13 (2016): 4686–89. http://dx.doi.org/10.1039/c6cy00473c.

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A new, cost-effective polystyrene-supported squaramide organocatalyst has been shown to mediate the highly enantioselective formation of pyranonaphthoquinones in flow through a sequential two-step process.

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34

Zamboulis, Alexandra, Nicolas J. Rahier, Matthias Gehringer, et al. "Silica-supported l-proline organocatalysts for asymmetric aldolisation." Tetrahedron: Asymmetry 20, no. 24 (2009): 2880–85. http://dx.doi.org/10.1016/j.tetasy.2009.11.024.

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35

Gruttadauria, Michelangelo, Francesco Giacalone, and Renato Noto. "Supported proline and proline-derivatives as recyclable organocatalysts." Chemical Society Reviews 37, no. 8 (2008): 1666. http://dx.doi.org/10.1039/b800704g.

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36

Nongrum, Ridaphun, Geetmani Singh Nongthombam, Mattilang Kharkongor, et al. "A nano-organo catalyzed route towards the efficient synthesis of benzo[b]pyran derivatives under ultrasonic irradiation." RSC Advances 6, no. 110 (2016): 108384–92. http://dx.doi.org/10.1039/c6ra24108e.

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37

Giacalone, Francesco, Michelangelo Gruttadauria, Paola Agrigento, Vincenzo Campisciano та Renato Noto. "Polystyrene-supported organocatalysts for α-selenenylation and Michael reactions". Catalysis Communications 16, № 1 (2011): 75–80. http://dx.doi.org/10.1016/j.catcom.2011.08.040.

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38

Polshettiwar, Vivek, Babita Baruwati, and Rajender S. Varma. "Magnetic nanoparticle-supported glutathione: a conceptually sustainable organocatalyst." Chemical Communications, no. 14 (2009): 1837. http://dx.doi.org/10.1039/b900784a.

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39

Piccardi, Riccardo, Anais Coffinet, Erica Benedetti, Serge Turcaud, and Laurent Micouin. "Continuous Flow Synthesis of Dimethylalkynylaluminum Reagents." Synthesis 48, no. 19 (2016): 3272–78. http://dx.doi.org/10.1055/s-0035-1561484.

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A new process for the synthesis of dimethylalkynylaluminum reagents under flow conditions is described. It involves a base-catalyzed alumination of terminal alkynes using a resin-supported organocatalyst. Final organometallic species are obtained in solution, and can further react with various aldehydes or nitrones.

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40

Kisszékelyi, Péter, Zsuzsanna Fehér, Sándor Nagy, et al. "Synthesis of C3-Symmetric Cinchona-Based Organocatalysts and Their Applications in Asymmetric Michael and Friedel–Crafts Reactions." Symmetry 13, no. 3 (2021): 521. http://dx.doi.org/10.3390/sym13030521.

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In this work, anchoring of cinchona derivatives to trifunctional cores (hub approach) was demonstrated to obtain size-enlarged organocatalysts. By modifying the cinchona skeleton in different positions, we prepared four C3-symmetric size-enlarged cinchona derivatives (hub-cinchonas), which were tested as organocatalysts and their catalytic activities were compared with the parent cinchona (hydroquinine) catalyst. We showed that in the hydroxyalkylation reaction of indole, hydroquinine provides good enantioselectivities (up to 73% ee), while the four new size-enlarged derivatives resulted in si

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41

Ma, Shuang, and Patrick Toy. "Self-Supported N-Heterocyclic Carbenes and Their Use as Organocatalysts." Molecules 21, no. 8 (2016): 1100. http://dx.doi.org/10.3390/molecules21081100.

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42

Rueping, Magnus, Erli Sugiono, Alexander Steck, and Thomas Theissmann. "Synthesis and Application of Polymer-Supported Chiral Brønsted Acid Organocatalysts." Advanced Synthesis & Catalysis 352, no. 2-3 (2010): 281–87. http://dx.doi.org/10.1002/adsc.200900746.

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43

Kristensen, Tor E., Kristian Vestli, Kim A. Fredriksen, Finn K. Hansen, and Tore Hansen. "Synthesis of Acrylic Polymer Beads for Solid-Supported Proline-Derived Organocatalysts." Organic Letters 11, no. 14 (2009): 2968–71. http://dx.doi.org/10.1021/ol901134v.

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44

Ferré, Meritxell, Xavier Cattoën, Michel Wong Chi Man, and Roser Pleixats. "Recyclable Silica-Supported Proline Sulphonamide Organocatalysts for Asymmetric Direct Aldol Reaction." ChemistrySelect 1, no. 21 (2016): 6741–48. http://dx.doi.org/10.1002/slct.201601859.

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45

Giacalone, Francesco, Michelangelo Gruttadauria, and Renato Noto. "ChemInform Abstract: Supported Organocatalysts as a Powerful Tool in Organic Synthesis." ChemInform 42, no. 13 (2011): no. http://dx.doi.org/10.1002/chin.201113255.

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46

Mrówczyński, Radosław, Alexandrina Nan, and Jürgen Liebscher. "Magnetic nanoparticle-supported organocatalysts – an efficient way of recycling and reuse." RSC Advances 4, no. 12 (2014): 5927. http://dx.doi.org/10.1039/c3ra46984k.

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47

Brunelli, Nicholas A., and Christopher W. Jones. "Tuning acid–base cooperativity to create next generation silica-supported organocatalysts." Journal of Catalysis 308 (December 2013): 60–72. http://dx.doi.org/10.1016/j.jcat.2013.05.022.

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48

Androvič, Ladislav, Pavel Drabina, Markéta Svobodová, and Miloš Sedlák. "Polystyrene supported benzoylthiourea—pyrrolidine organocatalyst for the enantioselective Michael addition." Tetrahedron: Asymmetry 27, no. 16 (2016): 782–87. http://dx.doi.org/10.1016/j.tetasy.2016.06.015.

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49

Ayats, Carles, Andrea H. Henseler, and Miquel A. Pericàs. "A Solid-Supported Organocatalyst for Continuous-Flow Enantioselective Aldol Reactions." ChemSusChem 5, no. 2 (2012): 320–25. http://dx.doi.org/10.1002/cssc.201100570.

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50

Abdelkawy, Mahmoud A., El-Saied A. Aly, Mahmoud A. El-Badawi, and Shinichi Itsuno. "Chitosan-supported cinchona urea: Sustainable organocatalyst for asymmetric Michael reaction." Catalysis Communications 146 (November 2020): 106132. http://dx.doi.org/10.1016/j.catcom.2020.106132.

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