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Journal articles on the topic 'Organocatalyst'

Author: Grafiati

Published: 4 June 2021

Last updated: 26 July 2025

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1

Shaikh, Isak Rajjak. "Organocatalysis: Key Trends in Green Synthetic Chemistry, Challenges, Scope towards Heterogenization, and Importance from Research and Industrial Point of View." Journal of Catalysts 2014 (March 26, 2014): 1–35. http://dx.doi.org/10.1155/2014/402860.

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This paper purports to review catalysis, particularly the organocatalysis and its origin, key trends, challenges, examples, scope, and importance. The definition of organocatalyst corresponds to a low molecular weight organic molecule which in stoichiometric amounts catalyzes a chemical reaction. In this review, the use of the term heterogenized organocatalyst will be exclusively confined to a catalytic system containing an organic molecule immobilized onto some sort of support material and is responsible for accelerating a chemical reaction. Firstly, a brief description of the field is provid

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2

Noraishah Abdullah, Zurina Shaameri, Ahmad Sazali Hamzah, and Mohd Fazli Mohammat. "Synthesis of Trans-4-Hydroxyprolineamide and 3-Ketoproline Ethyl Ester for Green Asymmetric Organocatalysts." Journal of Advanced Research in Applied Sciences and Engineering Technology 38, no. 1 (2024): 97–108. http://dx.doi.org/10.37934/araset.38.1.97108.

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Organocatalysts have become one of the three pillars in asymmetric reactions, along with metal catalysis and enzyme catalysis. Organocatalysis is widely acknowledged in both academia and industry as a practical and advantageous synthetic method owing to its operational ease, readily available catalyst, environmentally friendly, and minimal toxicity. Much attention has been focused on the organocatalyst for its superior properties as an efficient and clean catalyst. In this work, a series of green organocatalysts of trans-4-hydroxyprolineamide were efficiently obtained in a two-step reaction ut

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3

Srivastava, Vivek. "Ionic liquid mediated recyclable sulphonimide based organocatalysis for aldol reaction." Open Chemistry 8, no. 2 (2010): 269–72. http://dx.doi.org/10.2478/s11532-009-0140-x.

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AbstractSulphonimide based organocatalyst was used to catalyze the aldol reaction in ionic liquid media. On the basis of yield and selectivity the ionic liquid mediated system was found superior in comparison with organic solvents. The added advantages of this ionic liquid mediated organocatalysis are easy recovery of product and the recyclability of the organocatalyst.

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Li, Feifei, Wanting Yang, Mengmeng Li, and Lin Lei. "LED-induced controlled radical polymerization with an in situ bromine–iodine transformation and block polymerization combined with ring-opening polymerization using one organocatalyst." Polymer Chemistry 10, no. 29 (2019): 3996–4005. http://dx.doi.org/10.1039/c9py00685k.

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5

K, Gayathiri. "A Survey on Brain Tumor Segmentation Using Deep Learning for MRI Images." International Journal for Research in Applied Science and Engineering Technology 13, no. 2 (2025): 120–25. https://doi.org/10.22214/ijraset.2025.66771.

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The synthesis of aminobenzylnaphthols by organocatalysis has generated interest due to the mild reaction conditions and environmental benefits. It has been shown that (1,4-diazacyclo[2.2.2]octane) has demonstrated high efficiency as an organocatalyst for the three component condensation reaction. These reactions lead to the synthesis of a novel class of aminobenzylnaphthols under various solvent conditions offering remarkable advantages like: mild reaction conditions, high yields, selectivity and simplicity. This protocol is particularly appealing for the synthesis of complex organic molecules

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6

Rani, Sushma. "Optimization of Three Components, One Pot Synthesis of Aminobenzylnaphthol Exploiting Electrophilicity of Azomethines under Varying Conditions." International Journal for Research in Applied Science and Engineering Technology 13, no. 2 (2025): 126–36. https://doi.org/10.22214/ijraset.2025.66779.

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The synthesis of aminobenzylnaphthols by organocatalysis has generated interest due to the mild reaction conditions and environmental benefits. It has been shown that (1,4-diazacyclo[2.2.2]octane) has demonstrated high efficiency as an organocatalyst for the three component condensation reaction. These reactions lead to the synthesis of a novel class of aminobenzylnaphthols under various solvent conditions offering remarkable advantages like: mild reaction conditions, high yields, selectivity and simplicity. This protocol is particularly appealing for the synthesis of complex organic molecules

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Rani, Sushma. "Optimization of Three Component, One Pot Synthesis of aminobenzylnaphthol Exploiting Electrophilicity of azomethines Under Varying Conditions." International Journal for Research in Applied Science and Engineering Technology 13, no. 6 (2025): 1432–42. https://doi.org/10.22214/ijraset.2025.72431.

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The synthesis of aminobenzylnaphthols by organocatalysis has generated interest due to the mild reaction conditions and environmental benefits. It has been shown that (1,4-diazacyclo[2.2.2]octane) has demonstrated high efficiency as an organocatalyst for the three component condensation reaction. These reactions lead to the synthesis of a novel class of aminobenzylnaphthols under various solvent conditions offering remarkable advantages like: mild reaction conditions, high yields, selectivity and simplicity. This protocol is particularly appealing for the synthesis of complex organic molecules

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8

Malamiri, Fatemeh, Samad Khaksar, Rashid Badri, and Elham Tahanpesar. "Organocatalytic Combinatorial Synthesis of Quinazoline, Quinoxaline and Bis(indolyl)methanes." Combinatorial Chemistry & High Throughput Screening 23, no. 1 (2020): 83–88. http://dx.doi.org/10.2174/1386207323666191213123026.

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Aim and Objective: An efficient and practical procedure for the synthesis of heterocyclic compounds such as quinazolines, quinoxalines and bis(indolyl)methanes was developed using 3,5-bis(trifluoromethyl) phenyl ammonium hexafluorophosphate (BFPHP) as a novel organocatalyst. Material and Method: All of the obtained products are known compounds and identified by IR, 1HNMR, 13CNMR and melting points. Results: Various products were obtained in good to excellent yields under reaction conditions. Conclusion: The BFPHP organocatalyst demonstrates a novel class of non-asymmetric organocatalysts, whic

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9

Brozinski, Hannah L., Joshua P. Delaney, and Luke C. Henderson. "A Snapshot of Ionic-Liquid-Tagged Proline-Based Organocatalysts." Australian Journal of Chemistry 66, no. 8 (2013): 844. http://dx.doi.org/10.1071/ch13218.

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This highlight focuses on the developments in ionic-liquid (IL)-tagged proline-based organocatalysts. An overview of catalyst structure and application to asymmetric transformations is provided, and a representative synthesis of an IL-tagged organocatalyst is also discussed.

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10

Fredriksen, Kim A., Tor E. Kristensen, and Tore Hansen. "Combined bead polymerization and Cinchona organocatalyst immobilization by thiol–ene addition." Beilstein Journal of Organic Chemistry 8 (July 20, 2012): 1126–33. http://dx.doi.org/10.3762/bjoc.8.125.

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In this work, we report an unusually concise immobilization of Cinchona organocatalysts using thiol–ene chemistry, in which catalyst immobilization and bead polymerization is combined in a single step. A solution of azo initiator, polyfunctional thiol, polyfunctional alkene and an unmodified Cinchona-derived organocatalyst in a solvent is suspended in water and copolymerized on heating by thiol–ene additions. The resultant spherical and gel-type polymer beads have been evaluated as organocatalysts in catalytic asymmetric transformations.

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11

Nájera, Carmen, José Miguel Sansano, and Enrique Gómez-Bengoa. "Heterocycle-based bifunctional organocatalysts in asymmetric synthesis." Pure and Applied Chemistry 88, no. 6 (2016): 561–78. http://dx.doi.org/10.1515/pac-2016-0403.

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AbstractDifferent chiral bifunctional organocatalysts derived from trans-cyclohexane-1,2-diamine bearing different types of guanidine units able to form-hydrogen bonding activation have been designed. Conformational rigid 2-aminobenzimidazoles bearing a tertiary amino group have been used in enantioselective Michael type reactions of activated methylene compounds to nitroalkenes. The C2 symmetric bis(2-aminobenzimidazole) derivatives the appropriate organocatalyst for the conjugate addition of 1,3-dicarbonyl compounds to maleimides as well as for the SN1 reaction of benzylic alcohols with carb

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12

Zhang, Hong Ying, and Xue Ming Yan. "Efficient Enantioselective Michael Addition of Nitroalkenes Catalyzed by a New Surfactant-Type Thiourea Organocatalyst in Water." Advanced Materials Research 1015 (August 2014): 602–5. http://dx.doi.org/10.4028/www.scientific.net/amr.1015.602.

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A new surfactant-type bifunctional thiourea organocatalysts were synthesized. In the presence of 10 mol% PhCOOH, the Michael reaction of nitroalkenes with various nucleophiles could be catalyzed smoothly by this new organocatalyst in water at room temperature, giving the desired adducts in good yields with high diastereoselectivities (syn/anti=82/18->99/1) and excellent enantioselectivities (up to 97% ee)

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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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14

Miura, Tsuyoshi, Hiroshi Akutsu, Kosuke Nakashima, et al. "Design of Novel Hydrogen-Bonding Donor Organocatalysts and Their Application to Asymmetric Direct Aldol Reaction." Synlett 28, no. 11 (2017): 1363–67. http://dx.doi.org/10.1055/s-0036-1558971.

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Asymmetric catalytic activities of various organocatalysts bearing double hydrogen-bonding donor units showing different pK a values were examined for direct aldol reactions of cyclohexanone with aromatic aldehydes. Organocatalyst with motif exhibiting the highest acidity resulted in the corresponding aldol products with the highest enantioselectivity. A good correlation has been observed between the asymmetric catalytic activity for direct aldol reactions and acidities of double hydrogen-bonding donating units.

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15

Dargó, Gyula, Dóra Erdélyi, Balázs Molnár, Péter Kisszékelyi, Zsófia Garádi, and József Kupai. "A novel recyclable organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen." Beilstein Journal of Organic Chemistry 19 (November 24, 2023): 1811–24. http://dx.doi.org/10.3762/bjoc.19.133.

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Synthesizing organocatalysts is often a long and cost-intensive process, therefore, the recovery and reuse of the catalysts are particularly important to establish sustainable organocatalytic transformations. In this work, we demonstrate the synthesis, application, and recycling of a new lipophilic cinchona squaramide organocatalyst. The synthesized lipophilic organocatalyst was applied in Michael additions. The catalyst was utilized to promote the Michael addition of cyclohexyl Meldrum’s acid to 4-chloro-trans-β-nitrostyrene (quantitative yield, up to 96% ee). Moreover, 1 mol % of the catalys

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16

Félix, Ana Rita G., Pedro R. D. Simões, Francisco J. P. M. Sousa, M. Elisa Silva Serra, and Dina Murtinho. "Chiral Thiazolidine based Organocatalysts: Synthesis and Application in Asymmetric Aldol Reactions." Letters in Organic Chemistry 17, no. 5 (2020): 372–80. http://dx.doi.org/10.2174/2210681209666190807155816.

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Several novel chiral organocatalysts derived from thiazolidines containing amide and thioureia functionalities were synthesized in good yields. These organocatalysts were tested in the asymmetric aldol reaction of acetone with p-nitrobenzaldehyde. Reaction parameters such as reaction time, catalyst loading and solvent were optimized. Products with conversions up to 84% and enantiomeric ratios (er) up to 84.5:15.5 (R:S) were obtained. The effect of several chiral and non-chiral additives on the reactivity and selectivity of the reaction was also evaluated. The reaction was extended to other aro

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17

BOZKURT, Selahattin. "Asimetrik Michael Katılma Tepkimesi için Prolin bazlı β-Hidroksiamit Organokatalizörü". Afyon Kocatepe Üniversitesi Uluslararası Mühendislik Teknolojileri ve Uygulamalı Bilimler Dergisi 5, № 1 (2022): 13–17. http://dx.doi.org/10.53448/akuumubd.1111800.

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Applications of chiral organocatalysts in reaction types capable of forming C-C bonds, such as Michael addition, are one of the important research areas of recent years. One of the best examples of Michael addition, one of the important works of organic reaction types, is the reaction of nitroolefins with ketones in the presence of organocatalysts. In this study, L-proline-based amide derivative was synthesized with moderate yield and its structure was elucidated by various techniques. As an organocatalyst, its effect on enantiomeric excess (e.e.) was investigated in Michael addition studies a

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18

Ranaivoarimanana, Naliharifetra, Kyohei Kanomata, and Takuya Kitaoka. "Concerted Catalysis by Nanocellulose and Proline in Organocatalytic Michael Additions." Molecules 24, no. 7 (2019): 1231. http://dx.doi.org/10.3390/molecules24071231.

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Cellulose nanofibers (CNFs) have recently attracted much attention as catalysts in various reactions. Organocatalysts have emerged as sustainable alternatives to metal-based catalysts in green organic synthesis, with concerted systems containing CNFs that are expected to provide next-generation catalysis. Herein, for the first time, we report that a representative organocatalyst comprising an unexpected combination of 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO)-oxidized CNFs and proline shows significantly enhanced catalytic activity in an asymmetric Michael addition.

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19

Sahoo, Biswa Mohan, and Bimal Krishna Banik. "Organocatalysis: Trends of Drug Synthesis in Medicinal Chemistry." Current Organocatalysis 6, no. 2 (2019): 92–105. http://dx.doi.org/10.2174/2213337206666190405144423.

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Background:The continuous increase in challenges associated with the effective treatment of life threatening diseases influences the development of drug therapies with suitable physicochemical properties, efficiency and selectivity. So, organocatalysis is a potential synthetic tool which is accelerating the development of new drug molecules.Methods:Organocatalysis reactions can be carried out at lower temperatures and in milder pH conditions as compared to metal based catalysed reactions. Due to ready availability of catalysts, stability, purity, low toxicity and easy in handling of the chemic

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20

Tözendemir, Deniz, та Cihangir Tanyeli. "The synthesis of chiral β-naphthyl-β-sulfanyl ketones via enantioselective sulfa-Michael reaction in the presence of a bifunctional cinchona/sulfonamide organocatalyst". Beilstein Journal of Organic Chemistry 17 (18 лютого 2021): 494–503. http://dx.doi.org/10.3762/bjoc.17.43.

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Cinchona alkaloid-derived organocatalysts are widely employed in various asymmetric transformations, yielding products with high enantiopurity. In this respect, a bifunctional quinine-derived sulfonamide organocatalyst was developed to catalyze the asymmetric sulfa-Michael reaction of naphthalene-1-thiol with trans-chalcone derivatives. The target sulfa-Michael adducts were obtained with up to 96% ee under mild conditions and with a low (1 mol %) catalyst loading. Selected enantiomerically enriched sulfa-Michael addition products were subjected to oxidation to obtain the corresponding sulfones

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21

Keskin, Elif, Cigdem Yolacan, and Feray Aydogan. "Synthesis of New Di- and Triamides as Potential Organocatalysts for Asymmetric Aldol Reaction in Water." Acta Chimica Slovenica 67, no. 4 (2020): 1014–23. http://dx.doi.org/10.17344/acsi.2018.4748.

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New di- or triamide organocatalysts derived from (L)-proline were synthesized and successfully used in the direct asymmetric aldol reaction of aliphatic ketones and aromatic aldehydes in water at 0 °C in the presence of benzoic acid as co-catalyst. (S)-methyl-2-((S)-3-hydroxy-2-((S)-3-pyrrolidine-2-carboxamido)propanamido)-3-phenylpropanoate (7c) as organocatalyst showed best results under these reaction conditions, and good diastereoselectivities (up to 99%), enantioselectivities (up to 98%) and yields (up to 91%) were observed.

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Wang, Bing, Junjie Zhang, Yun Xue, et al. "Enhanced Catalytic Activity of TEMPO-Mediated Aerobic Oxidation of Alcohols via Redox-Active Metal–Organic Framework Nodes." Molecules 28, no. 2 (2023): 593. http://dx.doi.org/10.3390/molecules28020593.

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Metal–organic frameworks (MOFs) are outstanding platforms for heterogeneous catalysis due to their tunable pore size, huge surface area, large porosity, and potential active sites. The design and synthesis of MOF/organocatalyst co-catalytic systems have attracted considerable interest owing to their high catalytic activity, low toxicity, and mild reaction conditions. Herein, we reported the synthesis of a bifunctional TEMPO-IsoNTA organocatalyst featuring a pyridyl group as an anchoring site and a TEMPO radical as a catalytic active site. By using the topologically isomorphic structures of MIL

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Xu, En-Jie, Yan Song, Zhong-Lin Wei, et al. "Novel chiral proline-based organocatalysts with amide and thiourea–amine units for highly efficient asymmetric aldol reaction in saturated brine without additives." Canadian Journal of Chemistry 97, no. 5 (2019): 352–59. http://dx.doi.org/10.1139/cjc-2018-0352.

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A series of novel proline-based organocatalysts with amide and thiourea-amine units (7a–7f) were developed and evaluated in the asymmetric aldol reaction of 4-nitrobenzaldehyde with cyclohexanone. The organocatalyst (7c or 7d, 5 mol%) exhibited efficient catalytic activity to afford aldol products in high diastereoselectivity (up to >99:1), enantioselectivity (up to >99%), and yield (up to >96%) at 0 °C in saturated brine without adding an acid. Aldol products of benzaldehyde derivatives almost universally provide high diastereoselectivity and enantioselectivity.

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Agarwal, Shikha, Priyanka Kalal, Ayushi Sethiya, and Jay Soni. "Taurine: A Water Friendly Organocatalyst in Organic Reactions." Mini-Reviews in Organic Chemistry 19, no. 5 (2022): 617–28. http://dx.doi.org/10.2174/1570193x18666211122112327.

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: Organocatalysis has become a powerful tool in organic synthesis for the formation of C-C and C-X (N, S, O, etc.) bonds, leading to the formation of complex molecules from easily available starting materials. It provides an alternative platform to the conventional synthesis and fulfills the principles of green chemistry. During the last decades, taurine has emerged as a promising organocatalyst in an array of organic transformations in addition to its plentiful biological properties. It is highly stable, easy to store and separate, water-soluble, of low cost, easily available, and recyclable.

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Buchcic-Szychowska, Aleksandra, Stanisław Leśniak, and Michał Rachwalski. "Chiral Aziridine Phosphines as Highly Effective Promoters of Asymmetric Rauhut–Currier Reaction." Symmetry 14, no. 8 (2022): 1631. http://dx.doi.org/10.3390/sym14081631.

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A series of chiral enantiomerically pure aziridines containing a phosphine moiety were synthesized and successfully applied as organocatalysts in asymmetric intramolecular Rauhut–Currier reactions of p-quinone derivatives. The desired chiral phenols were achieved in high chemical yields and with satisfactory values of enantiomeric excess (up to 98% ee, in some cases). The stereochemical course of the title reaction may be controlled by the use of an appropriate enantiomer of the catalyst. The individual enantiomers of the organocatalyst led to the formation of specific enantiomers of the chira

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Kawka, Aleksandra, Karol Bester, Agnieszka Bukowska, and Wiktor Bukowski. "Salophen-Type Schiff Bases Functionalized with Pyridinium Halide Units as Metal-Free Catalysts for Synthesis of Cyclic Carbonates from Carbon Dioxide and Terminal Epoxides." Catalysts 14, no. 10 (2024): 658. http://dx.doi.org/10.3390/catal14100658.

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Objectives: Salophen-type Schiff bases functionalized with 4-(dimethylamino)pyridinium halide units are shown to be effective single-component catalysts for the synthesis of cyclic carbonates from terminal epoxides and carbon dioxide. Methods: Using one of such trifunctional organocatalysts, epichlorohydrin could be selectively converted to the target cyclic carbonate under 2 bar of CO2 at 120 °C. Results: Over 80% conversion of E3 was then observed when organocatalyst S3 was used in the amount of 0.5 mol% (TON = 156) and even the use of 0.05 mol% S3 guaranteed almost 50% conversion of E3 to C

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Brahmachari, Goutam, Nayana Nayek, Khondekar Nurjamal, Indrajit Karmakar, and Sanchari Begam. "Triethylamine — A Versatile Organocatalyst in Organic Transformations: A Decade Update." Synthesis 50, no. 21 (2018): 4145–64. http://dx.doi.org/10.1055/s-0037-1609909.

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Organocatalysts play pivotal roles in accomplishing a wide range of useful organic transformations, and organocatalytic reactions are now becoming powerful tools in the construction of simple to complex molecular scaffolds. This remarkable field is growing rapidly with new concepts and designs. During the recent past, triethylamine (or N,N-diethylethanamine), has emerged as an efficient organocatalyst in carrying out so many organic transformations, thereby producing interesting molecular frameworks. Triethylamine is relatively safe, commercially available and cheap. This review offers a decad

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Zakia Afzal, Zakia Afzal, and Naghmana Rashid and Humaira Nadeem Naghmana Rashid and Humaira Nadeem. "Stereoselective Synthesis, Spectral Characterization, Docking and Biological Screening of Coumarin Derivatives." Journal of the chemical society of pakistan 43, no. 3 (2021): 330. http://dx.doi.org/10.52568/000580/jcsp/43.03.2021.

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The compounds being synthesized in present research are chiral in nature so for getting enantiopure compounds, stereoselective synthesis was carried out by organocatalysis. The importance of enantiopure compounds can not be overstated because the living systems are chiral in nature and response of enantiomers can be very different in living systems. The organocatalysed synthesis was accumplished using 4-hydroxycoumarin and variously substituted dibenzylideneacetones as reactants and the organocatalyst being used was 9-amino-9-deoxyepiquinine. The range of enantioselectivity achieved was 24-95%

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Zakia Afzal, Zakia Afzal, and Naghmana Rashid and Humaira Nadeem Naghmana Rashid and Humaira Nadeem. "Stereoselective Synthesis, Spectral Characterization, Docking and Biological Screening of Coumarin Derivatives." Journal of the chemical society of pakistan 43, no. 3 (2021): 330. http://dx.doi.org/10.52568/000580.

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The compounds being synthesized in present research are chiral in nature so for getting enantiopure compounds, stereoselective synthesis was carried out by organocatalysis. The importance of enantiopure compounds can not be overstated because the living systems are chiral in nature and response of enantiomers can be very different in living systems. The organocatalysed synthesis was accumplished using 4-hydroxycoumarin and variously substituted dibenzylideneacetones as reactants and the organocatalyst being used was 9-amino-9-deoxyepiquinine. The range of enantioselectivity achieved was 24-95%

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Geng, Zhi-Cong, Jian Chen, Ning Li та ін. "Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives". Beilstein Journal of Organic Chemistry 8 (9 жовтня 2012): 1710–20. http://dx.doi.org/10.3762/bjoc.8.195.

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The catalytic synthesis of nitrogen-containing heterocycles is of great importance to medicinal and synthetic chemists, and also a challenge for modern chemical methodology. In this paper, we report the synthesis of pyrazolidine derivatives through a domino aza-Michael/hemiacetal sequence with chiral or achiral secondary amines as organocatalysts. Thus, a series of achiral pyrazolidine derivatives were obtained with good yields (up to 90%) and high diastereoselectivities (>20:1) with pyrrolidine as an organocatalyst, and enantioenriched pyrazolidines are also achieved with good results (up

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Guajardo, Nadia, Christoph R. Müller, Rodrigo Schrebler, Carlos Carlesi, and Pablo Domínguez de María. "Deep Eutectic Solvents for Organocatalysis, Biotransformations, and Multistep Organocatalyst/Enzyme Combinations." ChemCatChem 8, no. 6 (2015): 1020–27. http://dx.doi.org/10.1002/cctc.201501133.

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Wojaczyńska, Elżbieta, Franz Steppeler, Dominika Iwan, Marie-Christine Scherrmann, and Alberto Marra. "Synthesis and Applications of Carbohydrate-Based Organocatalysts." Molecules 26, no. 23 (2021): 7291. http://dx.doi.org/10.3390/molecules26237291.

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Organocatalysis is a very useful tool for the asymmetric synthesis of biologically or pharmacologically active compounds because it avoids the use of noxious metals, which are difficult to eliminate from the target products. Moreover, in many cases, the organocatalysed reactions can be performed in benign solvents and do not require anhydrous conditions. It is well-known that most of the above-mentioned reactions are promoted by a simple aminoacid, l-proline, or, to a lesser extent, by the more complex cinchona alkaloids. However, during the past three decades, other enantiopure natural compou

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Mondal, Anirban, and Kartick Chandra Bhowmick. "Asymmetric Direct Aldol Reaction Catalyzed by (1R, 2R)-(+)-1, 2- Diammonium Cyclohexane-L-tartrate in Water." Current Organocatalysis 6, no. 2 (2019): 165–70. http://dx.doi.org/10.2174/2213337206666181227151140.

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Background: A cheap and commercially available organocatalyst, (1R, 2R)-(+)-1, 2- diammonium cyclohexane-L-tartrate 1 was applied in direct aldol reaction in water. The organocatalyst 1 afforded aldol products from cyclohexanone and substituted aromatic aldehydes with high yield (up to 90%) and good stereoselectivity (up to 99% ee and up to 11.5:1 dr) in large volume of water (10 ml). Methods: The same aldol reaction when carried out in the presence of more expensive organocatalyst e.g. (1R, 2R)-(+)-1,2-diaminocyclohexane and 1,6-hexanediaoic acid as acid additive furnished the aldol products

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Faisca Phillips, Ana Maria, and Armando J. L. Pombeiro. "Atropselective Organocatalytic Synthesis of Chiral Compounds Containing Nitrogen along the Axis of Chirality." Symmetry 15, no. 6 (2023): 1261. http://dx.doi.org/10.3390/sym15061261.

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Atropisomers, i.e., stereoisomers that are distinct because their free rotation about a single bond is hindered by steric interactions between nearby bulky groups or by electrostatics, may interact with their surroundings in different ways, and may also exhibit different properties. They may be found as natural products, as pharmaceutical or agricultural active ingredients, as chiral ligands and organocatalysts, and in functional materials. Our ability to synthesize them stereoselectively and in a sustainable way, using achiral materials and simply with the aid of an organocatalyst and mild co

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35

Beletskaya, Irina P., and Alexei D. Averin. "New trends in the cross-coupling and other catalytic reactions." Pure and Applied Chemistry 89, no. 10 (2017): 1413–28. http://dx.doi.org/10.1515/pac-2016-1110.

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AbstractA mini-review covers the latest achievements in the field of metal-mediated cross-coupling reactions among which are palladium-catalyzed Heck, Suzuki, cyanation and amination reactions. The aspects of the application of Pd nanoparticles (PdNPs) are discussed. The possibilities of the applications of Cu(I)-catalyzed reactions are described. Special emphasis is made on the synthesis of polymacrocyclic compounds like porphyrin dyads and triads, polyazacryptands bearing fluorophore groups using catalytic methods. The application of Pd-catalyzed CH-activation reactions for porphyrin modific

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36

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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37

Çetin, Adnan, Ishak Bildirici, and Selçuk Gümüş. "Novel Pyrazole Derivatives Having Mono/Di Chiral Centered Group as Organocatalyst for Henry Reaction." Macedonian Journal of Chemistry and Chemical Engineering 39, no. 1 (2020): 17. http://dx.doi.org/10.20450/mjcce.2020.1954.

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The chiral substituted pyrazole-3-carboxamides (4a-c), pyrazole-3-carboxylates (5a-c), pyrazole-3-thioureides (7a-c) and pyrazole-3,4-dicarboxamides (10a-c) were prepared via the pyrazolo-3-chlorocarbonyl 2, pyrazolo-3,4-dicarboxy methyl ester 3 with pyrazole-3-isothiocyanate 6 with different (R)-chiral amino alcohols. All of the synthesized chiral compounds binding a pyrazole skeleton were investigated as organocatalysts for asymmetric aldol reactions between nitromethane and p-nitrobenzaldehyde in the presence of CuCl. Enantiomeric excesses and the reaction yields were found to be appropriat

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38

Shubina, Tatyana E., Matthias Freund, Sebastian Schenker, Timothy Clark, and Svetlana B. Tsogoeva. "Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity." Beilstein Journal of Organic Chemistry 8 (September 7, 2012): 1485–98. http://dx.doi.org/10.3762/bjoc.8.168.

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A new guanidine-thiourea organocatalyst has been developed and applied as bifunctional organocatalyst in the Michael addition reaction of diethyl malonate to trans-β-nitrostyrene. Extensive DFT calculations, including solvent effects and dispersion corrections, as well as ab initio calculations provide a plausible description of the reaction mechanism.

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39

Porcar, Raúl, Eduardo García-Verdugo, Belén Altava, Maria Isabel Burguete, and Santiago V. Luis. "Chiral Imidazolium Prolinate Salts as Efficient Synzymatic Organocatalysts for the Asymmetric Aldol Reaction." Molecules 26, no. 14 (2021): 4190. http://dx.doi.org/10.3390/molecules26144190.

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Chiral imidazolium l-prolinate salts, providing a complex network of supramolecular interaction in a chiral environment, have been studied as synzymatic catalytic systems. They are demonstrated to be green and efficient chiral organocatalysts for direct asymmetric aldol reactions at room temperature. The corresponding aldol products were obtained with moderate to good enantioselectivities. The influence of the presence of chirality in both the imidazolium cation and the prolinate anion on the transfer of chirality from the organocatalyst to the aldol product has been studied. Moreover, interes

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40

Jacoby, Caroline Gross, Jorge Hugo Sbardelotto, Tales da Silva Daitx, Bianca Thaís Dalberto, Raquel Santos Mauler та Paulo Henrique Schneider. "Poly(ε-caprolactones) Initiated by Chiral Compounds: A New Protocol to Support Organocatalysts". Catalysts 13, № 1 (2023): 164. http://dx.doi.org/10.3390/catal13010164.

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This work investigates the support of organocatalysts in polyesters, a class of polymers seldom used for this purpose. The proposal is to use the hydroxyl groups present in the structure of the chosen chiral compounds to promote the polymerization of ε-caprolactone, generating the support and anchoring the organocatalyst in a single step. A very simple method, with acid catalysis, was employed, that showed versatility in generating supported catalysts with different structures and functional groups and modulating the mass of the materials to generate specific solubility characteristics. In thi

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41

Vural, Ummu, Mustafa Durmaz, and Abdulkadir Sirit. "A novel calix[4]arene-based bifunctional squaramide organocatalyst for enantioselective Michael addition of acetylacetone to nitroolefins." Organic Chemistry Frontiers 3, no. 6 (2016): 730–36. http://dx.doi.org/10.1039/c6qo00135a.

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A new chiral calix[4]arene-based organocatalyst 3 bearing bis-squaramide moieties was designed and synthesized from p-tert-butylcalix[4]arene. This bifunctional organocatalyst was used in the enantioselective conjugate addition of acetyl acetone to β-nitrostyrenes. The corresponding adducts were obtained in good to excellent yields with high enantioselectivities.

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42

Shim, Jae Ho, Seok Hyun Cheun, Hyeon Soo Kim, and Deok-Chan Ha. "Enantioselective Organocatalyzed Michael Addition of Isobutyraldehyde to Maleimides in Aqueous Media." Molecules 27, no. 9 (2022): 2759. http://dx.doi.org/10.3390/molecules27092759.

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Thiourea was introduced into (R,R)-1,2-diphenylethylenediamine as an organocatalyst to promote the reaction between isobutyraldehydes and maleimides. Enantioselective Michael addition reaction was carried out as an eco-friendly method using water as the solvent. As a result of the reaction between isobutyraldehyde and maleimide, ≥97% yield and 99% enantioselectivity were obtained at a low catalyst loading of 0.01 mol%. The solvent effect can be explained by theoretical calculations that indicate the participation of a transition state, in which the CF3 substituent of the catalyst is a hydrogen

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43

Shim, Jae Ho, Seok Hyun Cheun, Hyeon Soo Kim, and Deok-Chan Ha. "Enantioselective Organocatalyzed Michael Addition of Isobutyraldehyde to Maleimides in Aqueous Media." Molecules 27, no. 9 (2022): 2759. http://dx.doi.org/10.3390/molecules27092759.

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Thiourea was introduced into (R,R)-1,2-diphenylethylenediamine as an organocatalyst to promote the reaction between isobutyraldehydes and maleimides. Enantioselective Michael addition reaction was carried out as an eco-friendly method using water as the solvent. As a result of the reaction between isobutyraldehyde and maleimide, ≥97% yield and 99% enantioselectivity were obtained at a low catalyst loading of 0.01 mol%. The solvent effect can be explained by theoretical calculations that indicate the participation of a transition state, in which the CF3 substituent of the catalyst is a hydrogen

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44

Thorat, Prashant B., Santosh V. Goswami, Wamanrao N. Jadhav, and Sudhakar R. Bhusare. "Water-Assisted Organocatalysis: An Enantioselective Green Protocol for the Henry Reaction." Australian Journal of Chemistry 66, no. 6 (2013): 661. http://dx.doi.org/10.1071/ch12428.

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We report an enantioselective Henry (nitroaldol) reaction catalysed by an organocatalyst using water as solvent. The enantioselective synthesis of β-nitroalcohols was achieved by using a neutral chiral organocatalyst, through strong hydrogen bonding, which results in the formation of corresponding products in excellent yield and enantioselectivity at room temperature. Other attractive features of the method are the eco-friendly, non-hazardous, and mild reaction conditions, inexpensive catalyst, and simple work up conditions.

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45

Tashakkorian, Hamed, Moslem Mansour Lakouraj, and Mona Rouhi. "p-Sulfonic Acid Calix[4]arene as an Efficient Catalyst for One-Pot Synthesis of Pharmaceutically Significant Coumarin Derivatives under Solvent-Free Condition." International Journal of Medicinal Chemistry 2015 (December 20, 2015): 1–8. http://dx.doi.org/10.1155/2015/738202.

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One-pot and efficient protocol for preparation of some potent pharmaceutically valuable coumarin derivatives under solvent-free condition via direct coupling using biologically nontoxic organocatalyst, calix[4]arene tetrasulfonic acid (CSA), was introduced. Calix[4]arene sulfonic acid has been incorporated lately as a magnificent and recyclable organocatalyst for the synthesis of some organic compounds. Nontoxicity, solvent-free conditions, good-to-excellent yields for pharmaceutically significant structures, and especially ease of catalyst recovery make this procedure valuable and environment

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46

Sohtome, Yoshihiro, Takahisa Yamaguchi, Shinji Tanaka, and Kazuo Nagasawa. "Sequential enantiodivergent organocatalysis: reversibility in enantioswitching controlled by a conformationally flexible guanidine/bisthiourea organocatalyst." Organic & Biomolecular Chemistry 11, no. 17 (2013): 2780. http://dx.doi.org/10.1039/c3ob27479a.

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47

Oudghiri, Khaoula, Zahira Belattmania, Hamid Elmouli, et al. "Mechanistic Insights into the Selective Synthesis of 4H-Pyran Derivatives On-Water Using Naturally Occurring Alginate from Sargassum muticum: Experimental and DFT Study." Gels 8, no. 11 (2022): 713. http://dx.doi.org/10.3390/gels8110713.

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The naturally occurring sodium alginate (SA) biopolymer from the Sargassum muticum (Yendo) Fensholt was employed as a green organocatalyst for the synthesis of 4H-pyran derivatives. The naturally extracted macromolecule was fully characterized using different analyses, including nuclear magnetic resonance (NMR), Fourier-transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), and Energy Dispersive X-ray Analysis (EDX). The catalytic activity of SA was investigated in the one-pot reaction between aldehydes, malononitrile, and 1,3-dicarbonyl compounds in water at room temperat

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48

Spiaggia, Fabio, Gloria Uccello Barretta, Anna Iuliano, Carlo Baldassari, Federica Aiello, and Federica Balzano. "A Squaramide-Based Organocatalyst as a Novel Versatile Chiral Solvating Agent for Carboxylic Acids." Molecules 29, no. 10 (2024): 2389. http://dx.doi.org/10.3390/molecules29102389.

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A squaramide-based organocatalyst for asymmetric Michael reactions has been tested as a chiral solvating agent (CSA) for 26 carboxylic acids and camphorsulfonic acid, encompassing amino acid derivatives, mandelic acid, as well as some of its analogs, propionic acids like profens (ketoprofen and ibuprofen), butanoic acids and others. In many cases remarkably high enantiodifferentiations at 1H, 13C and 19F nuclei were observed. The interaction likely involves a proton transfer from the acidic substrates to the tertiary amine sites of the organocatalyst, thus allowing for pre-solubilization of th

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49

Grand, Julien, Carole Alayrac, Simona Moldovan, and Bernhard Witulski. "Synthesis, Material Properties, and Organocatalytic Performance of Hypervalent Iodine(III)-Oxidants in Core–Shell-Structured Magnetic Nanoparticles." Catalysts 14, no. 10 (2024): 677. http://dx.doi.org/10.3390/catal14100677.

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Magnetic nanoparticles (MNPs) based on magnetite (Fe3O4) are attractive catalyst supports due to their high surface area, easy preparation, and facile separation, but they lack stability in acidic reaction media. The search for MNPs stable in oxidative acidic reaction media is a necessity if one wants to combine the advantages of MNPs as catalyst supports with those of iodine(III) reagents being environmentally benign oxidizers. In this work, immobilized iodophenyl organocatalysts on magnetite support (IMNPs) were obtained by crossed-linking polymerization of 4-iodostyrene with 1,4-divinylbenz

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50

Takagi, Koji, Nao Sakakibara, Shoko Kikkawa, and Seiji Tsuzuki. "Dicationic oligotelluroxane or mononuclear telluronium cation? Elucidation of the true catalytic species and activation mechanism of the benzylic carbon-halogen bond." Chemical Communications 57, no. 100 (2021): 13736–39. http://dx.doi.org/10.1039/d1cc06311a.

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