Organohalogen Chemistry and Catalysis

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 (31 August 2021) | Viewed by 23565

Special Issue Editors


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Institute of Physiology and Biochemistry ‘‘Ivan Djaja”, Faculty of Biology, University of Belgrade, Belgrade, Serbia
Interests: medicinal chemistry; physical organic chemistry; immunoinformatics
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Guest Editor
Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, Belgrade, Serbia
Interests: organic chemistry; azo dyes; heterocycles; halogen bonding
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear colleagues,

In recent years, the growing demand for a sustainable world has prompted an increasing need for environmentally-friendlier processes, acting therefore as a main driving force for the exploration of novel greener methodologies in organic chemistry. Development of effective, acid-free, and metal-free catalytic approaches for significant and established reactions has been on the rise in the last decade. Among the different investigated classes of molecules/catalysts, organohalogen compounds occupy special attention due to their ability to form halogen bonds. This noncovalent interaction provided by halogen atoms (acting as electron density acceptor sites—Lewis acid) in halo-organic molecules can be assumed as the main factor responsible for the significant catalytic activity of these compounds. During this interaction, for example, a significant increase of the positive charge on the carbon (from the carbonyl group) is formed, which allows for an easier attack of different nucleophiles and, therefore, superior and environmentally more acceptable reaction conditions.

This Special Issue is devoted to the applications of various organohalogen compounds, as catalysts or pre-catalysts, in the development of different organic reactions. Investigations of synthesis of potentially biologically active compounds applying one-pot multicomponent domino reactions are highly preferable. Moreover, reactions catalyzed by organohalogen compounds which follow the principles of the green chemistry are desired. Additionally, the investigations where organohalogen compounds are in the main focus of the paper (like reactants and/or products) are also preferable (halogenations, degradations of harmful organohalogen molecules etc). The potential topics of reviews and/or original research papers include but are not limited to:

  • Name reactions catalyzed by organohalogens;
  • Various organic reactions catalyzed by organohalogens;
  • Domino reactions catalyzed by organohalogens;
  • Synthesis of potentially biologically active compounds catalyzed by organohalogens;
  • Influence of halogen bond on catalytic activity of organohalogens and mechanism of organic reactions;
  • Oxidation and reduction reactions influenced by organohalogens;
  • Halogenations of organic molecules;
  • Degradations of harmful organohalogen molecules.

Dr. Bojan Božić
Dr. Jelena Ladjarević
Guest Editors

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Keywords

  • Organohalogen compounds
  • Catalysis
  • Halogen bond
  • Name reactions
  • Domino reactions
  • Oxidation/reduction reactions
  • Halogenations
  • Degradation
  • Sustainable processes
  • Green reactions

Related Special Issue

Published Papers (5 papers)

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Research

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12 pages, 704 KiB  
Article
Effects of Structured Solids on Regioselectivity of Dibromination of Naphthalene
by Keith Smith, Alaa K. H. Al-Khalaf, Kıymet Berkil Akar, Doaa J. K. Al-Badri, Benson M. Kariuki and Gamal A. El-Hiti
Catalysts 2021, 11(5), 540; https://doi.org/10.3390/catal11050540 - 23 Apr 2021
Cited by 1 | Viewed by 2444
Abstract
The influence of structured solids (amorphous, lamellar and 3D crystalline) on the regioselectivity of the dibromination of naphthalene using bromine at room temperature has been investigated. The more acidic amorphous catalysts and an acidic clay give rapid reactions and lead to a large [...] Read more.
The influence of structured solids (amorphous, lamellar and 3D crystalline) on the regioselectivity of the dibromination of naphthalene using bromine at room temperature has been investigated. The more acidic amorphous catalysts and an acidic clay give rapid reactions and lead to a large preponderance of 1,4-dibromonaphthalene over the 1,5-dibromo compound, while calcined KSF clay, a bentonite material, after a short reaction time gives a small predominance of the 1,5-isomer. Longer reaction times lead to the equilibration of reaction mixtures, which means that the 1,4-isomer eventually predominates in all cases. Based on these observations, it has been possible to devise synthetically useful preparative procedures, involving direct room temperature reactions of bromine with naphthalene, for either 1,4-dibromonaphthalene or 1,5-dibromonaphthalene based on the use of different solids, namely Synclyst 13 and KSF clay, respectively. Full article
(This article belongs to the Special Issue Organohalogen Chemistry and Catalysis)
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8 pages, 2783 KiB  
Article
N-Iodosuccinimide as a Precatalyst for Direct Cross-Coupling of Alcohols with C-Nucleophiles under Solvent-Free Reaction Conditions
by Njomza Ajvazi and Stojan Stavber
Catalysts 2020, 10(8), 850; https://doi.org/10.3390/catal10080850 - 01 Aug 2020
Cited by 5 | Viewed by 3284
Abstract
C–C bond formation is one of the most important implements in synthetic organic chemistry. In pursuit of effective synthetic routes functioning under greener pathways to achieve direct C–C bond formation, we report N-iodosuccinimide (NIS) as the most effective precatalyst among the N [...] Read more.
C–C bond formation is one of the most important implements in synthetic organic chemistry. In pursuit of effective synthetic routes functioning under greener pathways to achieve direct C–C bond formation, we report N-iodosuccinimide (NIS) as the most effective precatalyst among the N-halosuccinimides (NXSs) for the direct cross-coupling of benzyl alcohols with C-nucleophiles under solvent-free reaction conditions (SFRC). The protocol is metal-free, and air- and water-tolerant, providing a large-scale synthesis with almost quantitative yields. Full article
(This article belongs to the Special Issue Organohalogen Chemistry and Catalysis)
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20 pages, 5383 KiB  
Article
Strategy for Modifying Layered Perovskites toward Efficient Solar Light-Driven Photocatalysts for Removal of Chlorinated Pollutants
by Monica Raciulete, Florica Papa, Catalin Negrila, Veronica Bratan, Cornel Munteanu, Jeanina Pandele-Cusu, Daniela C. Culita, Irina Atkinson and Ioan Balint
Catalysts 2020, 10(6), 637; https://doi.org/10.3390/catal10060637 - 08 Jun 2020
Cited by 10 | Viewed by 2825
Abstract
We have explored an efficient strategy to enhance the overall photocatalytic performances of layered perovskites by increasing the density of hydroxyl group by protonation. The experimental procedure consisted of the slow replacement of interlayer Rb+ cation of RbLaTa2O7 Dion-Jacobson [...] Read more.
We have explored an efficient strategy to enhance the overall photocatalytic performances of layered perovskites by increasing the density of hydroxyl group by protonation. The experimental procedure consisted of the slow replacement of interlayer Rb+ cation of RbLaTa2O7 Dion-Jacobson (DJ) perovskite by H+ via acid treatment. Two layered perovskites synthesized by mild (1200 °C for 18 h) and harsh (950 and 1200 °C, for 36 h) annealing treatment routes were used as starting materials. The successful intercalation of proton into D-J interlayer galleries was confirmed by FTIR spectroscopy, thermal analyses, ion chromatography and XPS results. In addition, the ion-exchange route was effective to enlarge the specific surface area, thus enhancing the supply of photocharges able to participate in redox processes involved in the degradation of organic pollutants. HLaTa_01 protonated layered perovskite is reported as a efficient photocatalyst for photomineralization of trichloroethylene (TCE) to Cl and CO2 under simulated solar light. The enhanced activity is attributed to combined beneficial roles played by the increased specific surface area and high density of hydroxyl groups, leading to an efficiency of TCE mineralization of 68% moles after 5 h of irradiation. Full article
(This article belongs to the Special Issue Organohalogen Chemistry and Catalysis)
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Review

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58 pages, 15719 KiB  
Review
Tetramethylammonium Fluoride: Fundamental Properties and Applications in C-F Bond-Forming Reactions and as a Base
by Vladimir Iashin, Tom Wirtanen and Jesus E. Perea-Buceta
Catalysts 2022, 12(2), 233; https://doi.org/10.3390/catal12020233 - 18 Feb 2022
Cited by 9 | Viewed by 10449
Abstract
Nucleophilic ionic sources of fluoride are essential reagents in the synthetic toolbox to access high added-value fluorinated building blocks unattainable by other means. In this review, we provide a concise description and rationale of the outstanding features of one of these reagents, tetramethylammonium [...] Read more.
Nucleophilic ionic sources of fluoride are essential reagents in the synthetic toolbox to access high added-value fluorinated building blocks unattainable by other means. In this review, we provide a concise description and rationale of the outstanding features of one of these reagents, tetramethylammonium fluoride (TMAF), as well as disclosing the different methods for its preparation, and how its physicochemical properties and solvation effects in different solvents are intimately associated with its reactivity. Furthermore, herein we also comprehensively describe its historic and recent utilization, up to December 2021, in C-F bond-forming reactions with special emphasis on nucleophilic aromatic substitution fluorinations with a potential sustainable application in industrial settings, as well as its use as a base capable of rendering unprecedented transformations. Full article
(This article belongs to the Special Issue Organohalogen Chemistry and Catalysis)
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16 pages, 24138 KiB  
Review
Metal-Free Catalysts for the Polymerization of Alkynyl-Based Monomers
by Jie Zhang, Zhiming Zhang, Fulin Yang, Haoke Zhang, Jingzhi Sun and Benzhong Tang
Catalysts 2021, 11(1), 1; https://doi.org/10.3390/catal11010001 - 22 Dec 2020
Cited by 22 | Viewed by 3790
Abstract
Novel polymerizations based on alkyne monomers are becoming a powerful tool to construct polymers with unique structures and advanced functions in the areas of polymer and material sciences, and scientists have been attracted to develop a variety of novel polymerizations in recent decades. [...] Read more.
Novel polymerizations based on alkyne monomers are becoming a powerful tool to construct polymers with unique structures and advanced functions in the areas of polymer and material sciences, and scientists have been attracted to develop a variety of novel polymerizations in recent decades. Therein, catalytic systems play an indispensable role in the influence of polymerization efficiencies and the performances of the resultant polymers. Concerning the shortcomings of metallic catalysts, much of the recent research focus has been on metal-free polymerization systems. In this paper, metal-free catalysts are classified and the corresponding polymerizations are reviewed, including organobase-catalyzed polymerizations, Lewis-acid-catalyzed polymerizations, as well as catalyst-free polymerizations. Moreover, the challenges and perspectives in this area are also briefly discussed. Full article
(This article belongs to the Special Issue Organohalogen Chemistry and Catalysis)
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