Recent Advances in Catalytic Synthesis and Application of Heterocyclic and Heteroatom Compounds

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 (30 June 2023) | Viewed by 9241

Special Issue Editors


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Guest Editor
AE Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 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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Guest Editor
AE Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, Russia
Interests: : functionalized heteroatom compounds; organosulfur chemistry; vinylic heteroatom compounds; seleniranium intermediates; heterocyclic compounds; functionalization; theoretical studies
Special Issues, Collections and Topics in MDPI journals

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Guest Editor
AE Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, Russia
Interests: functionalized organochalcogen compounds; unsaturated organochalcogen compounds; selenium; tellurium; sulfur; heterocyclic compounds; functionalization
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The chemistry of heterocyclic and heteroatom compounds is a vast and important area of research. These compounds have attracted considerable attention due to their various valuable properties and diverse biological activities. Many of these compounds are useful ligands for transition metal catalysts, which play a huge role in modern organic synthesis.

The Special Issue will focus on the recent advances in catalytic synthesis and application of heterocyclic and heteroatom compounds. Original research articles and reviews describing advanced catalytic approaches and innovative methodologies are especially welcome. Contributions may cover all aspects of design, catalytic synthesis, and application of organic heteroatom and heterocyclic compounds. Particular attention will be paid to the synthesis of new efficient catalysts and compounds that mimic the catalytic functions of enzymes, including glutathione peroxidase.

Prof. Dr. Vladimir A. Potapov
Prof. Dr. Svetlana V. Amosova
Dr. Alexander V. Martynov
Guest Editors

Manuscript Submission Information

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Keywords

  • catalytic synthesis
  • heteroatom compounds
  • organic ligands
  • transition metal catalysts
  • heterocyclic chemistry
  • organic chalcogenides

Published Papers (8 papers)

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Research

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15 pages, 2503 KiB  
Article
First Examples of Reactions of 3-Trimethylsilyl-2-Propynamides and Organic Diselenides: Synthesis of Novel Derivatives of Propynamides
by Mikhail V. Andreev, Vladimir A. Potapov, Maxim V. Musalov and Lyudmila I. Larina
Catalysts 2023, 13(10), 1326; https://doi.org/10.3390/catal13101326 - 28 Sep 2023
Viewed by 739
Abstract
First examples of the reactions of 3-trimethylsilyl-2-propynamides with organic diselenides yielding 3-alkylselanyl-2-propenamides and 3-organylselanyl-2-propynamides were realized. The latter compounds were obtained by the Cu-catalyzed reaction of organic diselenides with 4-propioloylmorpholine. The reaction of 3-trimethylsilyl-2-propynamides with dialkyl diselenides in the system NaBH4/H [...] Read more.
First examples of the reactions of 3-trimethylsilyl-2-propynamides with organic diselenides yielding 3-alkylselanyl-2-propenamides and 3-organylselanyl-2-propynamides were realized. The latter compounds were obtained by the Cu-catalyzed reaction of organic diselenides with 4-propioloylmorpholine. The reaction of 3-trimethylsilyl-2-propynamides with dialkyl diselenides in the system NaBH4/H2O/K2CO3/THF proceeded in a regio- and stereoselective fashion, affording 3-alkylselanyl-2-propenamides in 90–94% yields. An unsymmetrical divinyl selenide with the cyclic amide groups and a product, containing two selanyl-2-propenamide moieties and three cyclic amide groups, were synthesized. The Cu-catalyzed allylation reaction of 3-trimethylsilyl-2-propynamides was accompanied with desilylation to yield 3-allyl-2-propynamides. Full article
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16 pages, 1607 KiB  
Article
A New Family of Vinyl Selenocyanates with the Amide Function Based on the Reaction of Potassium Selenocyanate with 3-Trimethylsilyl-2-Propynamides
by Mikhail V. Andreev, Vladimir A. Potapov, Maxim V. Musalov and Lyudmila I. Larina
Catalysts 2023, 13(9), 1257; https://doi.org/10.3390/catal13091257 - 30 Aug 2023
Viewed by 899
Abstract
An efficient approach to a novel family of (Z)-3-amino-3-oxo-1-propenyl selenocyanates was developed based on the reaction of KSeCN with 3-trimethylsilyl-2-propynamides in the presence of ammonium chloride in methanol. The reaction was accompanied by a desilylation process. The products were not formed under the [...] Read more.
An efficient approach to a novel family of (Z)-3-amino-3-oxo-1-propenyl selenocyanates was developed based on the reaction of KSeCN with 3-trimethylsilyl-2-propynamides in the presence of ammonium chloride in methanol. The reaction was accompanied by a desilylation process. The products were not formed under the same reaction conditions in the absence of ammonium chloride, which was used for the first time in the reactions of selenocyanates with acetylenes. The use of this new methodology allowed the reaction to carry out in a regio- and stereoselective fashion as anti-addition affording vinyl selenocyanates with a (Z)-configuration in high yields. Full article
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13 pages, 2796 KiB  
Article
Efficient Regioselective Synthesis of Novel Ensembles of Organylselanyl-Functionalized Divinyl Sulfides and 1,3-Thiaselenoles under Phase Transfer Catalysis Conditions
by Andrey S. Filippov, Svetlana V. Amosova, Nataliya A. Makhaeva, Alexander I. Albanov and Vladimir A. Potapov
Catalysts 2023, 13(8), 1227; https://doi.org/10.3390/catal13081227 - 21 Aug 2023
Viewed by 754
Abstract
Efficient regioselective synthesis of novel ensembles of organylselanyl-functionalized 1,3-thiaselenoles and divinyl sulfides in high yields under phase transfer catalysis conditions was developed. The methodology is based on the generation of sodium [(Z)-2-(vinylsulfanyl)ethenyl]selenolate and 1,3-thiaselenol-2-ylmethylselenolate, which were involved in a nucleophilic addition [...] Read more.
Efficient regioselective synthesis of novel ensembles of organylselanyl-functionalized 1,3-thiaselenoles and divinyl sulfides in high yields under phase transfer catalysis conditions was developed. The methodology is based on the generation of sodium [(Z)-2-(vinylsulfanyl)ethenyl]selenolate and 1,3-thiaselenol-2-ylmethylselenolate, which were involved in a nucleophilic addition reaction with activated alkenes such as acrylonitrile, acrylamide, methyl vinyl ketone, methyl, and ethyl acrylates. In the case of methyl vinyl ketone, the reaction was accompanied by the hydrogenation of the carbonyl group. Methylene chloride was involved in the nucleophilic substitution reaction with sodium [(Z)-2-(vinylsulfanyl)ethenyl]selenolate and 1,3-thiaselenol-2-ylmethylselenolate to afford new polyunsaturated compounds with several sulfur and selenium atoms. Full article
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13 pages, 3752 KiB  
Article
Triton-X-100 as an Organic Catalyst for One-Pot Synthesis of Arylmethyl-H-phosphinic Acids from Red Phosphorus and Arylmethyl Halides in the KOH/H2O/Toluene Multiphase Superbase System
by Vladimir A. Kuimov, Svetlana F. Malysheva, Natalia A. Belogorlova, Ruslan I. Fattakhov, Alexander I. Albanov and Boris A. Trofimov
Catalysts 2023, 13(4), 720; https://doi.org/10.3390/catal13040720 - 11 Apr 2023
Cited by 1 | Viewed by 1597
Abstract
Triton-X-100, a polyethylene glycol 4-(tert-octyl)phenyl ether, has been found to be an active micellar organic catalyst for the one-pot selective synthesis of arylmethyl-H-phosphinic acids in up to 65% yields by the direct phosphinylation of arylmethyl halides with red phosphorus [...] Read more.
Triton-X-100, a polyethylene glycol 4-(tert-octyl)phenyl ether, has been found to be an active micellar organic catalyst for the one-pot selective synthesis of arylmethyl-H-phosphinic acids in up to 65% yields by the direct phosphinylation of arylmethyl halides with red phosphorus in the KOH/H2O/toluene multiphase superbase system. The catalyst demonstrates a good recyclability. As a result, an expeditious method for the chemoselective synthesis of arylmethyl-H-phosphinic acids—versatile sought-after organophosphorus compounds—has been developed. The synthesis is implemented via direct alkylation/oxidation of red phosphorus with arylmethyl halides, promoted by superbase hydroxide anions using Triton-X-100 (a commercial off-the-shelf organic recyclable micellar catalyst). The reaction comprises the hydroxide anions-assisted disassembly of Pred 3D polymer molecules triggered by the separation from the potassium cation in ordinary crown-like micelles to produce polyphosphide anions in aqueous phase. Further, polyphosphide anions are alkylated with arylmethyl halides in organic phase in the presence of the catalytic Triton-X-100 reverse micelles and alkylated polyphosphide species undergo the double hydroxylation. The advantages of the strategy developed include chemoselectivity, benign and accessible starting reagents, catalyst recyclability, and facile one-pot implementation. Full article
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11 pages, 1951 KiB  
Article
1-Methylimidazole as an Organic Catalyst for [3+3]-Cyclodimerization of Acylethynylpyrroles to Bis(acylmethylidene)dipyrrolo[1,2-a:1′,2′-d]pyrazines
by Kseniya V. Belyaeva, Lina P. Nikitina, Veronika S. Gen’, Denis N. Tomilin, Lyubov N. Sobenina, Andrei V. Afonin, Ludmila A. Oparina and Boris A. Trofimov
Catalysts 2022, 12(12), 1604; https://doi.org/10.3390/catal12121604 - 7 Dec 2022
Cited by 3 | Viewed by 1358
Abstract
Acylethynylpyrroles, now readily available by the cross-coupling of pyrroles with acylbromoacetylenes in solid Al2O3 media, in the presence of 1-methylimidazole underwent unprecedentedly easy (40–45 °C) cyclodimerization into bis(acylmethylidene)dipyrrolo[1,2-a:1′,2′-d]pyrazines in up to 51% yield. Some other organic [...] Read more.
Acylethynylpyrroles, now readily available by the cross-coupling of pyrroles with acylbromoacetylenes in solid Al2O3 media, in the presence of 1-methylimidazole underwent unprecedentedly easy (40–45 °C) cyclodimerization into bis(acylmethylidene)dipyrrolo[1,2-a:1′,2′-d]pyrazines in up to 51% yield. Some other organic and inorganic basic catalysts can also trigger this cyclodimerization, but less efficiently. Full article
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12 pages, 1153 KiB  
Article
Pd/Cu-Catalyzed Cross-Coupling of Bis(2-bromovinyl) Selenides with Terminal Acetylenes: Unusual Involvement of Selanyl Function in the Sonogashira Reaction
by Alexander V. Martynov, Nataliya A. Makhaeva, Maxim V. Musalov, Alexander I. Albanov and Svetlana V. Amosova
Catalysts 2022, 12(12), 1589; https://doi.org/10.3390/catal12121589 - 6 Dec 2022
Viewed by 898
Abstract
The Pd/Cu-catalyzed Sonogashira reaction of (E,E)-bis(2-bromovinyl) selenide and (E,E)-bis(1-bromo-1-hexen-2-yl) selenide with terminal alkynes was found to proceed at room temperature involving both bromine atoms and the selanyl function. As a result, new bis-(1,3-enynyl) selenides and enediyne hydrocarbons are formed [...] Read more.
The Pd/Cu-catalyzed Sonogashira reaction of (E,E)-bis(2-bromovinyl) selenide and (E,E)-bis(1-bromo-1-hexen-2-yl) selenide with terminal alkynes was found to proceed at room temperature involving both bromine atoms and the selanyl function. As a result, new bis-(1,3-enynyl) selenides and enediyne hydrocarbons are formed with a complete retention of the stereoconfiguration of the initial selenides. Due to steric hindrances in the cross-coupling at the selenyl function in the case of (E,E)-bis(1-bromo-1-hexen-2-yl) selenide, the second process is realized to a lesser extent than with unsubstituted (E,E)-bis(2-bromovinyl) selenide. Full article
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Review

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29 pages, 8060 KiB  
Review
Recent Developments in the Synthesis of Organoselenium Compounds Based on the Reactions of Organic Diselenides with Acetylenes
by Maxim V. Musalov, Vladimir A. Potapov, Maria V. Musalova, Svetlana V. Amosova and Leonid B. Krivdin
Catalysts 2023, 13(10), 1369; https://doi.org/10.3390/catal13101369 - 15 Oct 2023
Cited by 1 | Viewed by 1366
Abstract
The last decade has witnessed significant progress in the development of novel synthetic methods for the preparation of a variety of new functionalized and condensed compounds via reactions of organic dichalcogenides with acetylenic derivatives. The present review highlights recent developments in the synthesis [...] Read more.
The last decade has witnessed significant progress in the development of novel synthetic methods for the preparation of a variety of new functionalized and condensed compounds via reactions of organic dichalcogenides with acetylenic derivatives. The present review highlights recent developments in the synthesis of organoselenium compounds based on the reactions of organic diselenides with acetylenes over the past few years. The discussion mainly focuses on the literature data for the last 5 years. It is worth noting that the lion’s share of this material is devoted to catalytic and electrophile-mediated reactions with aromatic compounds, containing a triple bond and nucleophilic functional groups. Full article
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20 pages, 4342 KiB  
Review
Recent Advances in Design and Synthesis of 1,3-Thiaselenolane and 1,3-Thiaselenole Derivatives
by Svetlana V. Amosova and Nataliya A. Makhaeva
Catalysts 2023, 13(8), 1221; https://doi.org/10.3390/catal13081221 - 17 Aug 2023
Viewed by 972
Abstract
Recent advances in the design and synthesis of five-membered heterocycles containing both sulfur and selenium atoms—1,3-thiaselenolane and 1,3-thiaselenole derivatives—are discussed in this review. These heterocyclic systems are of interest as intermediates for organic synthesis and compounds that can exhibit various useful properties, including [...] Read more.
Recent advances in the design and synthesis of five-membered heterocycles containing both sulfur and selenium atoms—1,3-thiaselenolane and 1,3-thiaselenole derivatives—are discussed in this review. These heterocyclic systems are of interest as intermediates for organic synthesis and compounds that can exhibit various useful properties, including biological activity and electrical conductivity. The main focus of the review is on the works of the last 20 years that make use of catalytic reactions. Synthetic methods for the preparation of structurally related 1,4,5,8-diselenadithiafulvalenes based on catalytic cross-coupling reactions are also presented. To date, the design and synthesis of 1,3-thiaselenolane and 1,3-thiaselenole derivatives have not been discussed in a separate review. Full article
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