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Organocatalysis in the Chemical Transformations
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Organocatalysis in the Chemical Transformations

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalysis in Organic and Polymer Chemistry".

Deadline for manuscript submissions: closed (1 August 2023) | Viewed by 17775

Special Issue Editor

Dr. Adriana Maria da Silva

E-Mail Website
Guest Editor
Instituto Nacional de Metrologia, Qualidade e Tecnologia (INMETRO), Duque de Caxias, RJ, Brazil
Interests: heterogeneous catalysis; catalysts synthesis; CO2 conversion; biomass conversion and sustainable process; graphene-based catalysts; supported-organocatalysts; nanometrology applied to catalysts
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Organocatalysis is a breakthrough in chemical transformations, offering innovation, superior activity, selectivity and, notably, a sustainable approach at a relatively low cost. It relies on the use of small organic molecules (isolated or attached to supports) with a huge range of applications, including fine chemistry, novel molecule synthesis, storage energy components, and photoredox and electrocatalytics processes. Organocatalysis was recognized as a tool for controlling the chirality of molecules by the Nobel Prize in Chemistry 2021, awarded for "the development of asymmetric organocatalysis."

Despite all these advantages, novel organocatalysts must be designed to meet the requirements for large-scale production. A combination of organic molecules with heterogeneous supports can advance manufacturing under the industrial perspective.

This issue is dedicated to organocatalysis, aiming to provide further insight into the organocatalysis research and positively contribute to the progression of this knowledge field. Therefore, our colleagues are invited to submit their valuable research to this special volume, including experimental and theoretical results.

Kind regards,

Prof. Dr. Adriana Maria da Silva
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Catalysts is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2200 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

 

Keywords

  • organocatalysis
  • heterogeneous organocatalysis
  • organocatalyzed reactions
  • metallo-organocatalysis
  • chiral
  • asymmetric
  • computational development

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Related Special Issue

Published Papers (9 papers)

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Editorial

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2 pages, 177 KiB  
Editorial
Organocatalysis in the Chemical Transformations
by Adriana Maria da Silva
Catalysts 2023, 13(9), 1282; https://doi.org/10.3390/catal13091282 - 7 Sep 2023
Viewed by 878
Abstract
Organocatalysis has been a breakthrough in chemical transformations becoming viable the conversion of challenging reactions through the sustainable use of small organic molecules as catalysts [...] Full article
(This article belongs to the Special Issue Organocatalysis in the Chemical Transformations)

Research

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10 pages, 1323 KiB  
Article
Similarities and Differences between Site-Selective Acylation and Phosphorylation of Amphiphilic Diols, Promoted by Nucleophilic Organocatalysts Decorated with Outer-Sphere Appendages
by Or Fleischer, Tom Targel, Fatma Saady and Moshe Portnoy
Catalysts 2023, 13(2), 361; https://doi.org/10.3390/catal13020361 - 7 Feb 2023
Cited by 3 | Viewed by 1432 | Correction
Abstract
We demonstrated recently that organocatalysts, based on a nucleophilic core (N-alkylimidazole or 4-aminopyridine) and decorated with an extensive secondary-sphere envelope (connected to the core through a benzyl substituent), strongly affect the site selectivity in acylation and phosphorylation of amphiphilic diols, sometimes entirely overriding [...] Read more.
We demonstrated recently that organocatalysts, based on a nucleophilic core (N-alkylimidazole or 4-aminopyridine) and decorated with an extensive secondary-sphere envelope (connected to the core through a benzyl substituent), strongly affect the site selectivity in acylation and phosphorylation of amphiphilic diols, sometimes entirely overriding the innate predisposition of the substrate. Preliminary studies pointed out that, despite some similarities, there are differences between the two transformations, regarding the influence of various catalyst features on the selectivity. To fully elucidate this, extended families of organocatalysts of the said design were examined, activity- and selectivity-wise, in the abovementioned transformations of model alcohol and amphiphilic diol substrates. A comparison of the influence of the catalyst design on the two reactions revealed that while the inductive electron donation of the o,o-dialkoxybenzyl substituent of the core, combined with the catalytic intermediate-stabilizing influence of some of the secondary-sphere components, causes an increase in the catalyst activity in both reactions and in the site selectivity in phosphorylation, its effect on the site selectivity in acylation is opposite. On the other hand, the lipophilicity of the secondary-sphere appendages improves the apolar site-favoring selectivity in both reactions. Thus, both factors work in concert in phosphorylation, but in opposite directions in acylation. Full article
(This article belongs to the Special Issue Organocatalysis in the Chemical Transformations)
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26 pages, 5668 KiB  
Article
Ring-Opening Polymerization of rac-Lactide Catalyzed by Octahedral Nickel Carboxylate Complexes
by Alexey Nikiforov, Natalia Panina, Daniil Blinou, Vladislav Gurzhiy, Juliya Nashchekina, Evgenia Korzhikova-Vlakh, Alexey Eremin and Mariia Stepanova
Catalysts 2023, 13(2), 304; https://doi.org/10.3390/catal13020304 - 29 Jan 2023
Cited by 5 | Viewed by 2819
Abstract
To date, nickel(II) complexes have not been practically investigated as catalysts in ring-opening polymerization (ROP) of lactide to produce biodegradable poly(lactic acid), which is in demand in biomedicine and industry. In this study, carboxylate complexes of nickel(II) containing various N-donor ligands with different [...] Read more.
To date, nickel(II) complexes have not been practically investigated as catalysts in ring-opening polymerization (ROP) of lactide to produce biodegradable poly(lactic acid), which is in demand in biomedicine and industry. In this study, carboxylate complexes of nickel(II) containing various N-donor ligands with different nuclearity, metal core rigidity and nature of carboxylate ligands were synthesized and studied by infrared spectroscopy, X-ray diffraction, elemental and thermogravimetric analyses. The obtained complexes were examined in the ROP of the rac-lactide in bulk and in toluene solution with and without the addition of a benzyl alcohol initiator. In the series of complexes studied, the complex [Ni(DBED)2(O2CC(CH3)3)2]·(CH3)3CCO2H (DBED is N,N′-dibenzylethylenediamine) was a syndioselective catalyst and showed the highest catalytic ability in the polymerization without the addition of benzyl alcohol. For this complex, according to 1D DOSY 1H NMR spectroscopy and mass spectrometry with electrospray ionization, polymerization is initiated by a free secondary amine, DBED, leaving the metal’s inner coordination sphere. Based on the experimental data obtained, a comprehensive density functional theory (DFT) study of the ROP pathways including the initiation and first chain growth cycle steps with a detailed description of the intermediates and evaluation of the energy barriers of the steps was carried out. It was shown that one of the key roles in the reaction process is played by carboxylate ligands, which act as proton carriers from the initiator molecule and have a significant influence on the reactivity of the catalytic metal complexes. Full article
(This article belongs to the Special Issue Organocatalysis in the Chemical Transformations)
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16 pages, 1745 KiB  
Article
Development of L-Proline-Based Chiral Ionic Liquids for Asymmetric Michael Reaction
by Karolina Zalewska, Isabel Pinto, Luis Cabrita, Małgorzata E. Zakrzewska, João P. Noronha, M. Nunes da Ponte and Luis C. Branco
Catalysts 2023, 13(2), 270; https://doi.org/10.3390/catal13020270 - 25 Jan 2023
Cited by 3 | Viewed by 2231
Abstract
Different Chiral Ionic Liquids (CIL) based on L-proline have been developed. Simple and efficient synthetic methodologies are used, allowing preparation in good yields for twelve novel CILs using L-proline as a cation or anion combined with suitable counter-ions. A detailed physical and chemical [...] Read more.
Different Chiral Ionic Liquids (CIL) based on L-proline have been developed. Simple and efficient synthetic methodologies are used, allowing preparation in good yields for twelve novel CILs using L-proline as a cation or anion combined with suitable counter-ions. A detailed physical and chemical characterization of the CILs was performed to evaluate the influence of counter-ions on the final properties. The most promissory CILs were tested as efficient chiral catalysts in IL media for asymmetric Michael addition reactions of ketones and aldehydes to nitro-olefins. Similar or even better conversions and enantioselectivities (ee up to 95%) compared to the original L-proline were achieved. Additionally, a good product extraction performance using supercritical CO2 processes was obtained. Full article
(This article belongs to the Special Issue Organocatalysis in the Chemical Transformations)
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14 pages, 3868 KiB  
Article
Poly(ε-caprolactones) Initiated by Chiral Compounds: A New Protocol to Support Organocatalysts
by Caroline Gross Jacoby, Jorge Hugo Sbardelotto, Tales da Silva Daitx, Bianca Thaís Dalberto, Raquel Santos Mauler and Paulo Henrique Schneider
Catalysts 2023, 13(1), 164; https://doi.org/10.3390/catal13010164 - 10 Jan 2023
Cited by 2 | Viewed by 1505
Abstract
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 [...] Read more.
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 this way, the catalysts can be solubilized in some organic solvents, such as dichloromethane, but at the end of the reaction, they can be recovered in a heterogeneous way, through precipitation in more apolar solvents. The materials were applied as organocatalysts on an aldol addition test reaction and the product could be obtained in excellent yields and good stereoselectivity. The polymer did not show signs of degradation after the reaction, proving to be robust and suitable for use in catalysis; however, a recycling process appears to be necessary for its reuse. Full article
(This article belongs to the Special Issue Organocatalysis in the Chemical Transformations)
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Review

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27 pages, 6778 KiB  
Review
Organocatalytic Transformations from Sulfur Ylides
by Marcio Hayashi and Antonio C. B. Burtoloso
Catalysts 2023, 13(4), 689; https://doi.org/10.3390/catal13040689 - 31 Mar 2023
Cited by 10 | Viewed by 2748
Abstract
Sulfur ylides are an important class of organic compounds due to their ability to perform many different transformations that can give diverse and interesting products with a high degree of complexity. Although metal-catalyzed transformations are frequent in this class of compounds, organocatalyzed transformations [...] Read more.
Sulfur ylides are an important class of organic compounds due to their ability to perform many different transformations that can give diverse and interesting products with a high degree of complexity. Although metal-catalyzed transformations are frequent in this class of compounds, organocatalyzed transformations remain scarce. From initial works, this review aims to show organocatalyzed transformations from sulfur ylides, involving cyclopropanation and formal N–H, S–H, and C–H insertion reactions, including enantioselective versions. The proposed mechanisms and the modes of activation of these organocatalysts will be covered. Furthermore, advances in this area and potential challenges to be circumvented in the near future will also be discussed. Full article
(This article belongs to the Special Issue Organocatalysis in the Chemical Transformations)
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52 pages, 13982 KiB  
Review
Recent Advances in Greener Asymmetric Organocatalysis Using Bio-Based Solvents
by Lorena S. R. Martelli, Ingrid V. Machado, Jhonathan R. N. dos Santos and Arlene G. Corrêa
Catalysts 2023, 13(3), 553; https://doi.org/10.3390/catal13030553 - 9 Mar 2023
Cited by 6 | Viewed by 2486
Abstract
Efficient synthetic methods that avoid the extensive use of hazardous reagents and solvents, as well as harsh reaction conditions, have become paramount in the field of organic synthesis. Organocatalysis is notably one of the best tools in building chemical bonds between carbons and [...] Read more.
Efficient synthetic methods that avoid the extensive use of hazardous reagents and solvents, as well as harsh reaction conditions, have become paramount in the field of organic synthesis. Organocatalysis is notably one of the best tools in building chemical bonds between carbons and carbon-heteroatoms; however, most examples still employ toxic volatile organic solvents. Although a portfolio of greener solvents is now commercially available, only ethyl alcohol, ethyl acetate, 2-methyltetrahydrofuran, supercritical carbon dioxide, ethyl lactate, and diethyl carbonate have been explored with chiral organocatalysts. In this review, the application of these bio-based solvents in asymmetric organocatalytic methods reported in the last decade is discussed, highlighting the proposed mechanism pathway for the transformations. Full article
(This article belongs to the Special Issue Organocatalysis in the Chemical Transformations)
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Other

2 pages, 157 KiB  
Correction
Correction: Fleischer et al. Similarities and Differences between Site-Selective Acylation and Phosphorylation of Amphiphilic Diols, Promoted by Nucleophilic Organocatalysts Decorated with Outer-Sphere Appendages. Catalysts 2023, 13, 361
by Or Fleischer, Tom Targel, Fatma Saady and Moshe Portnoy
Catalysts 2023, 13(7), 1098; https://doi.org/10.3390/catal13071098 - 14 Jul 2023
Viewed by 625
Abstract
The authors wish to make the following corrections to this paper [...] Full article
(This article belongs to the Special Issue Organocatalysis in the Chemical Transformations)
10 pages, 949 KiB  
Perspective
Usefulness of the Global E Factor as a Tool to Compare Different Catalytic Strategies: Four Case Studies
by Achille Antenucci and Stefano Dughera
Catalysts 2023, 13(1), 102; https://doi.org/10.3390/catal13010102 - 3 Jan 2023
Cited by 4 | Viewed by 1761
Abstract
The global E factor (EG factor) has recently been introduced, in the context of asymmetric organocatalysis, as a new green chemistry metric to take into consideration the synthesis of the catalyst in the overall economy of the synthetic process of a [...] Read more.
The global E factor (EG factor) has recently been introduced, in the context of asymmetric organocatalysis, as a new green chemistry metric to take into consideration the synthesis of the catalyst in the overall economy of the synthetic process of a given chiral molecule in optically pure form. Herein, its further usefulness in comparing diverse catalytic systems, even different from organocatalysts, is shown by the analysis of four case studies. Full article
(This article belongs to the Special Issue Organocatalysis in the Chemical Transformations)
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