Synthesis and Catalytic Applications of S-, Se- and Te-Containing Compounds: Recent Advances in Organic Synthesis

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 October 2022) | Viewed by 15345

Special Issue Editors


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Dipartimento di Chimica "Ugo Schiff" Università degli Studi di Firenze, Via della Lastruccia, 13 – 50019 Sesto Fiorentino (Firenze), Italy
Interests: synthesis and reactivity of organosulfur, organoselenium and organotellurium compounds, also mediated by organosilanes; study of their properties as new antioxidants and enzyme modulators; synthesis and functionalization of heterocyclic compounds

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Guest Editor
Dipartimento di Chimica “Ugo Schiff”, Università degli Studi di Firenze, Via della Lastruccia, 13–50019 Sesto Fiorentino, FI, Italy
Interests: selenium; tellurium; catalysis; green chemistry; redox; functional group interconversions; synthetic methodologies; enzyme modulators
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Special Issue Information

Dear Colleagues,

Chalcogen-containing organic molecules (S, Se, Te) occupy a relevant position in the chemical sciences, finding a steadily growing application in organic synthesis, catalysis, materials science, and polymer chemistry. Furthermore, such molecules play an increasingly important role in biology and in medicinal chemistry. For example, a number of organoselenium and organotellurium compounds have exhibited remarkable catalytic antioxidant activity. In this scenario, owing to their unique properties, organochalcogenides have in recent decades attracted a great deal of interest among organic chemists, biologists, and medicinal chemists, as proven by the growing number of studies focusing on these topics.

The possibility to introduce a variety of functional groups and the opportunity to access a plethora of highly diversified chalcogen-containing structures are of paramount importance in order to successfully develop new synthetically and biologically valuable systems. Therefore, the development of new synthetic methodologies towards these classes of compounds, as well as the study of their environmentally friendly synthetic and catalytic applications, represent one of the more fascinating challenges ahead in this field.

This Special Issue will be focusing on experimental, theoretical, and applicative studies involving sulfur-, selenium-, and tellurium-containing molecules. Particular emphasis will be devoted on recent advances in the synthesis of chalcogenated systems and in the study of their catalytic properties. Applications in the field of organic transformations, sustainable processes, material science, biology, and medicinal chemistry will be covered.

Prof. Dr. Antonella Capperucci
Dr. Damiano Tanini
Guest Editors

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Keywords

  • sulfur
  • selenium
  • tellurium
  • synthetic methodologies
  • green chemistry
  • sustainable processes
  • glutathione peroxidase-like systems
  • enzyme modulators and mimics
  • polymers and materials
  • density functional theory
  • spectroscopic properties

Published Papers (4 papers)

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Research

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22 pages, 10864 KiB  
Article
Ionic Liquids-Assisted Ring Opening of Three-Membered Heterocycles with Thio- and Seleno-Silanes
by Damiano Tanini, Tommaso Pecchi, Nikolai V. Ignat’ev and Antonella Capperucci
Catalysts 2022, 12(10), 1259; https://doi.org/10.3390/catal12101259 - 17 Oct 2022
Cited by 1 | Viewed by 1237
Abstract
Ring opening reactions of strained heterocycles (epoxides, aziridines, thiiranes) by silyl chalcogenides, such as thiosilanes and selenosilanes, can be efficiently performed in a variety of ionic liquids, which can behave as reaction media and in some cases also as catalysts. This protocol enables [...] Read more.
Ring opening reactions of strained heterocycles (epoxides, aziridines, thiiranes) by silyl chalcogenides, such as thiosilanes and selenosilanes, can be efficiently performed in a variety of ionic liquids, which can behave as reaction media and in some cases also as catalysts. This protocol enables an alternative access to β-functionalized sulfides and selenides under mild conditions. Full article
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Review

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60 pages, 18968 KiB  
Review
Lighting Up the Organochalcogen Synthesis: A Concise Update of Recent Photocatalyzed Approaches
by Ricardo H. Bartz, Luiz H. Dapper, Jean C. Kazmierczak, Ricardo F. Schumacher, Gelson Perin, Samuel Thurow, Filipe Penteado and Eder J. Lenardão
Catalysts 2023, 13(3), 520; https://doi.org/10.3390/catal13030520 - 03 Mar 2023
Cited by 2 | Viewed by 1734
Abstract
This review describes the recent advances in photocatalyzed reactions to form new carbon–sulfur and carbon–selenium bonds. With a total of 136 references, of which 81 articles are presented, the authors introduce in five sections an updated picture of the state of the art [...] Read more.
This review describes the recent advances in photocatalyzed reactions to form new carbon–sulfur and carbon–selenium bonds. With a total of 136 references, of which 81 articles are presented, the authors introduce in five sections an updated picture of the state of the art in the light-promoted synthesis of organochalcogen compounds (from 2019 to present). The light-promoted synthesis of sulfides by direct sulfenylation of C–C π-bonds; synthesis of sulfones; the activation of Csp2N bond in the formation of Csp2S bonds; synthesis of thiol ester, thioether and thioacetal; and the synthesis of organoselenium compounds are discussed, with detailed reaction conditions and selected examples for each protocol. Full article
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13 pages, 3196 KiB  
Review
Recent Advances in the Synthesis of Isothiocyanates Using Elemental Sulfur
by András Gy. Németh and Péter Ábrányi-Balogh
Catalysts 2021, 11(9), 1081; https://doi.org/10.3390/catal11091081 - 08 Sep 2021
Cited by 5 | Viewed by 3501
Abstract
Isothiocyanates (ITCs) are biologically active molecules found in several natural products and pharmaceutical ingredients. Moreover, due to their high and versatile reactivity, they are widely used as intermediates in organic synthesis. This review considers the best practices for the synthesis of ITCs using [...] Read more.
Isothiocyanates (ITCs) are biologically active molecules found in several natural products and pharmaceutical ingredients. Moreover, due to their high and versatile reactivity, they are widely used as intermediates in organic synthesis. This review considers the best practices for the synthesis of ITCs using elemental sulfur, highlighting recent developments. First, we summarize the in situ generation of thiocarbonyl surrogates followed by their transformation in the presence of primary amines leading to ITCs. Second, carbenes and amines afford isocyanides, and the further reaction of this species with sulfur readily generates ITCs under thermal, catalytic or basic conditions. Additionally, we also reveal that in the catalyst-free reaction of isocyanides and sulfur, two—until this time overlooked and not investigated—different mechanistic pathways exist. Full article
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11 pages, 2680 KiB  
Review
Carbonic Anhydrases: Versatile and Useful Biocatalysts in Chemistry and Biochemistry
by Andrea Angeli, Fabrizio Carta and Claudiu T. Supuran
Catalysts 2020, 10(9), 1008; https://doi.org/10.3390/catal10091008 - 03 Sep 2020
Cited by 38 | Viewed by 7812
Abstract
Metalloenzymes such as the carbonic anhydrases (CAs, EC 4.2.1.1) possess highly specialized active sites that promote fast reaction rates and high substrate selectivity for the physiologic reaction that they catalyze, hydration of CO2 to bicarbonate and a proton. Among the eight genetic [...] Read more.
Metalloenzymes such as the carbonic anhydrases (CAs, EC 4.2.1.1) possess highly specialized active sites that promote fast reaction rates and high substrate selectivity for the physiologic reaction that they catalyze, hydration of CO2 to bicarbonate and a proton. Among the eight genetic CA macrofamilies, α-CAs possess rather spacious active sites and show catalytic promiscuity, being esterases with many types of esters, but also acting on diverse small molecules such as cyanamide, carbonyl sulfide (COS), CS2, etc. Although artificial CAs have been developed with the intent to efficiently catalyse non-biologically related chemical transformations with high control of stereoselectivity, the activities of these enzymes were much lower when compared to natural CAs. Here, we report an overview on the catalytic activities of α-CAs as well as of enzymes which were mutated or artificially designed by incorporation of transition metal ions. In particular, the distinct catalytic mechanisms of the reductase, oxidase and metatheses-ase such as de novo designed CAs are discussed. Full article
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