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Organoselenium Reagents and Their Applications
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Organoselenium Reagents and Their Applications

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (28 February 2021) | Viewed by 27433

Special Issue Editor

Prof. Dr. Francesca Marini

E-Mail Website
Guest Editor
Department of Pharmaceutical Sciences, University of Perugia Via del Liceo 1, 06100 Perugia, Italy
Interests: heterocycles; stereoselective synthesis; one-pot reactions; multicomponent reactions; organocatalytic methods; organoselenium chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

In the last few decades organoselenium chemistry has rapidly grown and it is now considered a powerful tool in the hand of organic chemists. Organoselenium reagents have been the object of intense synthetic and mechanistic studies. Electrophilic or nucleophilic reagents, as well as radical precursors, have been synthesized and used for reliable and general synthetic transformations. New applications of selenium chemistry have appeared in attractive areas of synthetic organic chemistry such as sustainable chemistry, heterocycle synthesis, natural product synthesis, stereoselective reactions, catalysis, and asymmetric synthesis. Moreover, a great number of selenium-containing compounds has been synthesized and biologically evaluated in the frame of drug discovery projects. The aim of this Special Issue is to collect original research papers and review articles focused on all the above-mentioned aspects of selenium research.

Prof. Dr. Francesca Marini
Guest Editor

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Keywords

  • Selenium
  • Nucleophiles
  • Electrophiles
  • Radical
  • Heterocycles
  • Stereoselective processes
  • Asymmetric synthesis
  • Sustainable synthesis

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Published Papers (6 papers)

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Research

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10 pages, 8005 KiB  
Article
Influence of Fluorine Substituents on the Electronic Properties of Selenium-N-Heterocyclic Carbene Compounds
by Mohamad Shazwan Shah Jamil and Nor Azam Endot
Molecules 2020, 25(21), 5161; https://doi.org/10.3390/molecules25215161 - 6 Nov 2020
Cited by 13 | Viewed by 3284
Abstract
N-heterocyclic carbenes (NHCs) are common ancillary ligands in organometallic compounds that are used to alter the electronic and steric properties of a metal centre. To date, various NHCs have been synthesised with different electronic properties, which can be done by modifying the [...] Read more.
N-heterocyclic carbenes (NHCs) are common ancillary ligands in organometallic compounds that are used to alter the electronic and steric properties of a metal centre. To date, various NHCs have been synthesised with different electronic properties, which can be done by modifying the backbone or changing the nitrogen substituents group. This study describes a systematic modification of NHCs by the inclusion of fluorine substituents and examines the use of selenium-NHC compounds to measure the π-accepting ability of these fluorinated NHC ligands. Evaluation of the 77Se NMR chemical shifts of the selenium adducts reveals that fluorinated NHCs have higher chemical shifts than the non-fluorinated counterparts, IMes and IPh. Higher 77Se NMR chemical shifts values indicate a stronger π-accepting ability of the NHC ligands. The findings of this study suggest that the presence of fluorine atoms has increased the π-accepting ability of the corresponding NHC ligands. This work supports the advantage of the 77Se NMR chemical shifts of selenium-NHC compounds for assessing the influence of fluorine substituents on NHC ligands. Full article
(This article belongs to the Special Issue Organoselenium Reagents and Their Applications)
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13 pages, 2474 KiB  
Article
Phenylselanyl Group Incorporation for “Glutathione Peroxidase-Like” Activity Modulation
by Magdalena Obieziurska-Fabisiak, Agata J. Pacuła, Lucia Capoccia, Joanna Drogosz-Stachowicz, Anna Janecka, Claudio Santi and Jacek Ścianowski
Molecules 2020, 25(15), 3354; https://doi.org/10.3390/molecules25153354 - 24 Jul 2020
Cited by 12 | Viewed by 4121
Abstract
The ability of organoselenium molecules to mimic the activity of the antioxidant selenoenzyme glutathione peroxidase (GPx) allows for their use as antioxidant or prooxidant modulators in several diseases associated with the disruption of the cell redox homeostasis. Current drug design in the field [...] Read more.
The ability of organoselenium molecules to mimic the activity of the antioxidant selenoenzyme glutathione peroxidase (GPx) allows for their use as antioxidant or prooxidant modulators in several diseases associated with the disruption of the cell redox homeostasis. Current drug design in the field is partially based on specific modifications of the known Se-therapeutics aimed at achieving more selective bioactivity towards particular drug targets, accompanied by low toxicity as the therapeutic window for organoselenium compounds tends to be very narrow. Herein, we present a new group of Se-based antioxidants, structurally derived from the well-known group of GPx mimics—benzisoselenazol-3(2H)-ones. A series of N-substituted unsymmetrical phenylselenides with an o-amido function has been obtained by a newly developed procedure: a copper-catalyzed nucleophilic substitution by a Se-reagent formed in situ from diphenyl diselenide and sodium borohydride. All derivatives were tested as antioxidants and anticancer agents towards breast (MCF-7) and leukemia (HL-60) cancer cell lines. The highest H2O2-scavenging potential was observed for N-(3-methylbutyl)-2-(phenylselanyl)benzamide. The best antiproliferative activity was found for (−)-N-(1S,2R,4R)-menthyl-2-(phenylselanyl)benzamide (HL-60) and ((−)-N-(1S,2R,3S,6R)-(2-caranyl))benzamide (MCF-7). The structure–activity correlations, including the differences in reactivity of the obtained phenyl selenides and corresponding benzisoselenazol-3(2H)-ones, were performed. Full article
(This article belongs to the Special Issue Organoselenium Reagents and Their Applications)
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15 pages, 10008 KiB  
Article
A Simple Zinc-Mediated Method for Selenium Addition to Michael Acceptors
by Francesca Giulia Nacca, Bonifacio Monti, Eder João Lenardão, Paul Evans and Claudio Santi
Molecules 2020, 25(9), 2018; https://doi.org/10.3390/molecules25092018 - 26 Apr 2020
Cited by 12 | Viewed by 4773
Abstract
In this work, we focused our attention on seleno-Michael type reactions. These were performed using zinc-selenolates generated in situ from diphenyl diselenide 1, 1,2-bis(3-phenylpropyl)diselenide 30, and protected selenocystine 31 via an efficient biphasic Zn/HCl-based reducing system. Alkenes with a variety of [...] Read more.
In this work, we focused our attention on seleno-Michael type reactions. These were performed using zinc-selenolates generated in situ from diphenyl diselenide 1, 1,2-bis(3-phenylpropyl)diselenide 30, and protected selenocystine 31 via an efficient biphasic Zn/HCl-based reducing system. Alkenes with a variety of electron-withdrawing groups were investigated in order to gauge the scope and limitations of the process. Results demonstrated that the addition to acyclic α,β-unsaturated ketones, aldehydes, esters amides, and acids was effectively achieved and that alkyl substituents at the reactive β-centre can be accommodated. Similarly, cyclic enones undergo efficient Se-addition and the corresponding adducts were isolated in moderate to good yield. Vinyl sulfones, α,β-unsaturated nitriles, and chalcones are not compatible with these reaction conditions. A recycling experiment demonstrated that the unreacted Zn/HCl reducing system can be effectively reused for seven reaction cycles (91% conversion yield at the 7° recycling rounds). Full article
(This article belongs to the Special Issue Organoselenium Reagents and Their Applications)
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17 pages, 3010 KiB  
Article
Remarkable Alkene-to-Alkene and Alkene-to-Alkyne Transfer Reactions of Selenium Dibromide and PhSeBr. Stereoselective Addition of Selenium Dihalides to Cycloalkenes
by Vladimir A. Potapov, Maxim V. Musalov, Evgeny O. Kurkutov, Vladimir A. Yakimov, Alfiya G. Khabibulina, Maria V. Musalova, Svetlana V. Amosova, Tatyana N. Borodina and Alexander I. Albanov
Molecules 2020, 25(1), 194; https://doi.org/10.3390/molecules25010194 - 3 Jan 2020
Cited by 10 | Viewed by 4655
Abstract
The original goal of this research was to study stereochemistry of selenium dihalides addition to cycloalkenes and properties of obtained products. Remarkable alkene-to-alkene and alkene-to-alkyne transfer reactions of selenium dibromide and PhSeBr were discovered during this research. The adducts of selenium dibromide with [...] Read more.
The original goal of this research was to study stereochemistry of selenium dihalides addition to cycloalkenes and properties of obtained products. Remarkable alkene-to-alkene and alkene-to-alkyne transfer reactions of selenium dibromide and PhSeBr were discovered during this research. The adducts of selenium dibromide with alkenes or cycloalkenes easily exchange SeBr2 with other unsaturated compounds, including acetylenes, at room temperature, in acetonitrile. Similar alkene-to-alkene and alkene-to-alkyne transfer reactions of the PhSeBr adducts with alkenes or cycloalkenes take place. The supposed reaction pathway includes the selenium group transfer from seleniranium species to alkenes or alkynes. It was found that the efficient SeBr2 and PhSeBr transfer reagents are Se(CH2CH2Br)2 and PhSeCH2CH2Br, which liberate ethylene, leading to a shift in equilibrium. The regioselective and stereoselective synthesis of bis(E-2-bromovinyl) selenides and unsymmetrical E-2-bromovinyl selenides was developed based on the SeBr2 and PhSeBr transfer reactions which proceeded with higher selectivity compared to analogous addition reactions of SeBr2 and PhSeBr to alkynes under the same conditions. Full article
(This article belongs to the Special Issue Organoselenium Reagents and Their Applications)
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Review

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25 pages, 5991 KiB  
Review
Modern Synthetic Strategies with Organoselenium Reagents: A Focus on Vinyl Selenones
by Martina Palomba, Italo Franco Coelho Dias, Ornelio Rosati and Francesca Marini
Molecules 2021, 26(11), 3148; https://doi.org/10.3390/molecules26113148 - 25 May 2021
Cited by 14 | Viewed by 3011
Abstract
In recent years, vinyl selenones were rediscovered as useful building blocks for new synthetic transformations. This review will highlight these advances in the field of multiple-bond-forming reactions, one-pot synthesis of carbo- and heterocycles, enantioselective construction of densely functionalized molecules, and total synthesis of [...] Read more.
In recent years, vinyl selenones were rediscovered as useful building blocks for new synthetic transformations. This review will highlight these advances in the field of multiple-bond-forming reactions, one-pot synthesis of carbo- and heterocycles, enantioselective construction of densely functionalized molecules, and total synthesis of natural products. Full article
(This article belongs to the Special Issue Organoselenium Reagents and Their Applications)
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103 pages, 50843 KiB  
Review
Recent Advances in the Synthesis of Selenophenes and Their Derivatives
by Paola S. Hellwig, Thiago J. Peglow, Filipe Penteado, Luana Bagnoli, Gelson Perin and Eder J. Lenardão
Molecules 2020, 25(24), 5907; https://doi.org/10.3390/molecules25245907 - 13 Dec 2020
Cited by 25 | Viewed by 6579
Abstract
The selenophene derivatives are an important class of selenium-based heterocyclics. These compounds play an important role in prospecting new drugs, as well as in the development of new light-emitting materials. During the last years, several methods have been emerging to access the selenophene [...] Read more.
The selenophene derivatives are an important class of selenium-based heterocyclics. These compounds play an important role in prospecting new drugs, as well as in the development of new light-emitting materials. During the last years, several methods have been emerging to access the selenophene scaffold, employing a diversity of cyclization-based synthetic strategies, involving specific reaction partners and particularities. This review presents a comprehensive discussion on the recent advances in the synthesis of selenophene-based compounds, starting from different precursors, highlighting the main differences, the advantages, and limitations among them. Full article
(This article belongs to the Special Issue Organoselenium Reagents and Their Applications)
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