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Recent Advances in Organoselenium Chemistry

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

Deadline for manuscript submissions: closed (31 May 2022) | Viewed by 12723

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Guest Editor
AE Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciencesdisabled, Irkutsk, Russia
Interests: chalcogen-containing heterocycles; functionalized organoselenium compounds; chalcogen electrophilic reagents; organotellurium compounds; chalcogen cyclofunctionalization reactions; vinyl chalcogenides; chalcogen annelation reactions
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Special Issue Information

Dear Colleagues,

Recently, scientists working in various fields of selenium chemistry and biochemistry celebrated two centuries of selenium research, which started in 1817, when selenium was discovered by the Swedish chemists Berzelius and Gahn. However, selenium chemistry was a neglected field for the biggest part of these two centuries. Today, selenium is recognized as an essential micronutrient for human beings. The discovery of the biological role of selenium served as a powerful impetus for the intensive development of organoselenium chemistry, which has now taken an important place in chemical research. It is worth noting that many cutting-edge investigations in organoselenium chemistry have made important contributions to other sciences including biochemistry and materials science.

This Special Issue welcomes original research articles or review articles from colleagues working in the various fields of organoselenium chemistry. Special attention will be paid to the development of novel approaches to organoselenium compounds exhibiting biological activity and advanced synthetic methodology. Contributions to this issue may cover all aspects of organoselenium chemistry, including synthesis, functionalization, and applications of organoselenium compounds.

Prof. Dr. Vladimir A. Potapov
Guest Editor

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Keywords

  • Organoselenium compounds
  • Organic selenides
  • Selenium reagents
  • Selenium heterocycles
  • Functionalization

Published Papers (5 papers)

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Research

11 pages, 5540 KiB  
Article
An Efficient Method for Selective Syntheses of Sodium Selenide and Dialkyl Selenides
by Na Hye Shin, Yoo Jin Lim, Chorong Kim, Ye Eun Kim, Yu Ra Jeong, Hyunsung Cho, Myung-Sook Park and Sang Hyup Lee
Molecules 2022, 27(16), 5224; https://doi.org/10.3390/molecules27165224 - 16 Aug 2022
Cited by 4 | Viewed by 2386
Abstract
The studies on the selective synthesis of dialkyl selenide compounds 1 were presented. Overcoming the complexity and difficulty of selenides (R-Se-R) and/or multiselenides (R-Sen-R; n ≥ 2), we aimed to optimize the reaction condition for the tolerable preparation of sodium selenide [...] Read more.
The studies on the selective synthesis of dialkyl selenide compounds 1 were presented. Overcoming the complexity and difficulty of selenides (R-Se-R) and/or multiselenides (R-Sen-R; n ≥ 2), we aimed to optimize the reaction condition for the tolerable preparation of sodium selenide (Na2Se) by reducing Se with NaBH4, and then to achieve selective syntheses of dialkyl selenides 1 by subsequently treating the obtained sodium selenide with alkyl halides (RX). Consequently, various dialkyl selenides 1 were efficiently synthesized in good-to-moderate yields. The investigations on reaction pathways and solvent studies were also described. Full article
(This article belongs to the Special Issue Recent Advances in Organoselenium Chemistry)
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24 pages, 4672 KiB  
Article
Synthesis, Reactivity and Antimicrobial Activity of a Series of 2-Arylamino-1,3-selenazoles
by Julia Kuchar, Katharina Reinhold, Vera Rösgen, Nils Nöthling, Christian W. Lehmann and Fabian Mohr
Molecules 2021, 26(24), 7695; https://doi.org/10.3390/molecules26247695 - 20 Dec 2021
Cited by 4 | Viewed by 2551
Abstract
A series of 2-arylamino-1,3-selenazoles was synthesized and their reactivity was studied. The 2-arylamino-1,3-selenazoles and their reaction products were characterized by various spectroscopic methods and X-ray diffraction. In addition, the antimicrobial activity of the 2-arylamino-1,3-selenazoles in a panel of seven bacteria and fungi was [...] Read more.
A series of 2-arylamino-1,3-selenazoles was synthesized and their reactivity was studied. The 2-arylamino-1,3-selenazoles and their reaction products were characterized by various spectroscopic methods and X-ray diffraction. In addition, the antimicrobial activity of the 2-arylamino-1,3-selenazoles in a panel of seven bacteria and fungi was examined. Full article
(This article belongs to the Special Issue Recent Advances in Organoselenium Chemistry)
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15 pages, 2083 KiB  
Article
A Regioselective Synthesis of Novel Functionalized Organochalcogen Compounds by Chalcogenocyclofunctionalization Reactions Based on Chalcogen Halides and Natural Products
by Maxim V. Musalov, Vladimir A. Potapov, Vladimir A. Yakimov, Maria V. Musalova, Arkady A. Maylyan, Sergey V. Zinchenko and Svetlana V. Amosova
Molecules 2021, 26(12), 3729; https://doi.org/10.3390/molecules26123729 - 18 Jun 2021
Cited by 4 | Viewed by 2078
Abstract
The regioselective synthesis of novel functionalized condensed organochalcogen compounds by chalcogenocyclofunctionalization reactions based on chalcogen halides and the natural products thymol and carvacrol has been developed. The reactions of selenium dibromide with allyl thymol and allyl carvacrol proceeded in methylene chloride at room [...] Read more.
The regioselective synthesis of novel functionalized condensed organochalcogen compounds by chalcogenocyclofunctionalization reactions based on chalcogen halides and the natural products thymol and carvacrol has been developed. The reactions of selenium dibromide with allyl thymol and allyl carvacrol proceeded in methylene chloride at room temperature in the presence of NaHCO3 affording bis[(7-isopropyl-4-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl] and bis[(4-isopropyl-7-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl] selenides in 90–92% yield. Similar sulfides were obtained in 70–72% yields by the reaction of sulfur dichloride in chloroform under reflux. Trihalotellanes containing the same organic moieties were synthesized from allyl thymol, allyl carvacrol and tellurium tetrachloride or tetrabromide in quantitative yields. Corresponding functionalized ditellurides were prepared in 91–92% yields by the reduction of the trichlorotellanes with sodium metabisulfite in two-phase solvent system. The comparison of reactivity of sulfur, selenium and tellurium halides in chalcogenocyclofunctionalization and distinguishing features of each reaction were discussed. Full article
(This article belongs to the Special Issue Recent Advances in Organoselenium Chemistry)
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14 pages, 2069 KiB  
Article
Synthesis of 3,4-Bis(Butylselanyl)Selenophenes and 4-Alkoxyselenophenes Promoted by Oxone®
by Paola S. Hellwig, Jonatan S. Guedes, Angelita M. Barcellos, Gelson Perin and Eder J. Lenardão
Molecules 2021, 26(8), 2378; https://doi.org/10.3390/molecules26082378 - 19 Apr 2021
Cited by 4 | Viewed by 2348
Abstract
We describe herein an alternative transition-metal-free procedure to access 3,4-bis(butylselanyl)selenophenes and the so far unprecedented 3-(butylselanyl)-4-alkoxyselenophenes. The protocol involves the 5-endo-dig electrophilic cyclization of 1,3-diynes promoted by electrophilic organoselenium species, generated in situ through the oxidative cleavage of the Se-Se bond [...] Read more.
We describe herein an alternative transition-metal-free procedure to access 3,4-bis(butylselanyl)selenophenes and the so far unprecedented 3-(butylselanyl)-4-alkoxyselenophenes. The protocol involves the 5-endo-dig electrophilic cyclization of 1,3-diynes promoted by electrophilic organoselenium species, generated in situ through the oxidative cleavage of the Se-Se bond of dibutyl diselenide using Oxone® as a green oxidant. The selective formation of the title products was achieved by controlling the solvent identity and the amount of dibutyl diselenide. By using 4.0 equiv of dibutyl diselenide and acetonitrile as solvent at 80 °C, four examples of 3,4-bis(butylselanyl)selenophenes were obtained in moderate to good yields (40–78%). When 3.0 equiv of dibutyl diselenide were used, in the presence of aliphatic alcohols as solvent/nucleophiles under reflux, 10 3-(butylselanyl)-4-alkoxyselenophenes were selectively obtained in low to good yields (15–80%). Full article
(This article belongs to the Special Issue Recent Advances in Organoselenium Chemistry)
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15 pages, 2101 KiB  
Article
(Z,Z)-Selanediylbis(2-propenamides): Novel Class of Organoselenium Compounds with High Glutathione Peroxidase-Like Activity. Regio- and Stereoselective Reaction of Sodium Selenide with 3-Trimethylsilyl-2-propynamides
by Mikhail V. Andreev, Vladimir A. Potapov, Maxim V. Musalov and Svetlana V. Amosova
Molecules 2020, 25(24), 5940; https://doi.org/10.3390/molecules25245940 - 15 Dec 2020
Cited by 7 | Viewed by 2108
Abstract
The efficient regio- and stereoselective synthesis of (Z,Z)-3,3′-selanediylbis(2-propenamides) in 76–93% yields was developed based on the reaction of sodium selenide with 3-trimethylsilyl-2-propynamides. (Z,Z)-3,3′-Selanediylbis(2-propenamides) are a novel class of organoselenium compounds. To date, not a single [...] Read more.
The efficient regio- and stereoselective synthesis of (Z,Z)-3,3′-selanediylbis(2-propenamides) in 76–93% yields was developed based on the reaction of sodium selenide with 3-trimethylsilyl-2-propynamides. (Z,Z)-3,3′-Selanediylbis(2-propenamides) are a novel class of organoselenium compounds. To date, not a single representative of 3,3′-selanediylbis(2-propenamides) has been described in the literature. Studying glutathione peroxidase-like properties by a model reaction showed that the activity of the obtained products significantly varies depending on the organic moieties in the amide group. Divinyl selenide, which contains two lipophilic cyclohexyl substituents in the amide group, exhibits very high glutathione peroxidase-like activity and this compound is considerably superior to other products in this respect. Full article
(This article belongs to the Special Issue Recent Advances in Organoselenium Chemistry)
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