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Organic Chemistry, Synthesis, and Catalysis: Special Issue in Memory of Professor Victor Snieckus for His Outstanding Contributions to Organic Chemistry

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

Deadline for manuscript submissions: closed (31 May 2022) | Viewed by 25367

Special Issue Editors


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Guest Editor
Department of Chemistry, Université Clermont Auvergne, Clermont-Ferrand, France
Interests: design and synthesis of heteroaromatic compounds; biologically active agents; kinases inhibitors

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Guest Editor
Departamento de Química Orgánica e Inorgánica, Facultad de Ciencia y Tecnología, Universidad del País Vasco / Euskal Herriko Unibertsitatea UPV/EHU, Apdo. 644., 48080 Bilbao, Spain
Interests: organic synthesis; stereoselective synthesis; asymmetric catalysis; organometallic reagents; cross-coupling reactions; C-H activation; heterocycles

Special Issue Information

Dear Colleagues,

Victor Snieckus (1937–2020) was an internationally recognized organic chemist, particularly due to his outstanding contributions in organometallic chemistry. He conducted pioneering work in organolithium chemistry, in the methodological development of directed ortho metalation (DoM) and directed remote metalation (DreM) reactions, whose synthetic applications, combined with other methodologies, such as cross-coupling, metathesis, etc., opened elegant and efficient routes in a wide variety of (hetero)aromatic compounds. His contributions have had a great impact not only from an academic point of view, but also due to their industrial application in pharmaceutical and agrochemical industries.

As a result, along his long and productive career, Vic received numerous and important awards and fellowships, many also related to pharmaceutical industry. However, in addition to his impressive scientific contributions, Vic was also highly involved in teaching, training, and mentoring young researchers. An outstanding number of international undergraduate/PhD/post-Doc students have been trained in his laboratories at the University of Waterloo or at Queen’s University. Those of us that were lucky to be, years ago, one of those young researchers that had the opportunity to work with him can account for his deep and extensive knowledge of chemistry, his passion and enthusiasm, and his ability to communicate that passion. His open and thoughtful character, as well as his interest in traditional (non-chemistry) group activities (skiing, skating, street hockey, Christmas parties, welcome and farewell parties, Cardinal Puff, VS group T-shirts, etc.) were crucial indeed in maintain an excellent working atmosphere within the VS group.

We are honored to act as Guest Editors of this Special Issue in Molecules to celebrate Vic’s contributions to organic chemistry, with gratitude for his exemplary work through the years.

We are pleased to invite you submit papers on organic chemistry, synthesis, and catalysis. We really appreciate your effort and attention to this Special Issue.

Prof. Dr. Pascale Moreau
Prof. Dr. Nuria Sotomayor
Guest Editors

Manuscript Submission Information

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Keywords

  • organometallic chemistry
  • organic chemistry
  • catalysis
  • synthesis
  • synthetic methodology

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Published Papers (11 papers)

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Research

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14 pages, 2077 KiB  
Article
Synthesis and Stereochemical Characterization of a Novel Chiral α-Tetrazole Binaphthylazepine Organocatalyst
by Assunta Summa, Patrizia Scafato, Sandra Belviso, Guglielmo Monaco, Riccardo Zanasi, Giovanna Longhi, Sergio Abbate and Stefano Superchi
Molecules 2022, 27(16), 5113; https://doi.org/10.3390/molecules27165113 - 11 Aug 2022
Cited by 2 | Viewed by 1474
Abstract
A novel α-tetrazole-substituted 1,1′-binaphthylazepine chiral catalyst has been synthesized and its absolute configuration has been determined by DFT computational analysis of the vibrational circular dichroism (VCD) spectrum of its precursor. The VCD analysis, carried out through the model averaging method, allowed to assign [...] Read more.
A novel α-tetrazole-substituted 1,1′-binaphthylazepine chiral catalyst has been synthesized and its absolute configuration has been determined by DFT computational analysis of the vibrational circular dichroism (VCD) spectrum of its precursor. The VCD analysis, carried out through the model averaging method, allowed to assign the absolute configuration of a benzylic stereocenter in the presence of a chiral binaphthyl moiety. The 1,1′-binaphthylazepine tetrazole and the nitrile its immediate synthetic precursor, have been preliminarily tested as chiral organocatalysts in the asymmetric intramolecular oxa-Michael cyclization of 2-hydroxy chalcones for the synthesis of chiral flavanones obtaining low enantioselectivity. Full article
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9 pages, 816 KiB  
Communication
A Fluoroponytailed NHC–Silver Complex Formed from Vinylimidazolium/AgNO3 under Aqueous–Ammoniacal Conditions
by Gabriel Partl, Marcus Rauter, Lukas Fliri, Thomas Gelbrich, Christoph Kreutz, Thomas Müller, Volker Kahlenberg, Sven Nerdinger and Herwig Schottenberger
Molecules 2022, 27(13), 4137; https://doi.org/10.3390/molecules27134137 - 28 Jun 2022
Cited by 1 | Viewed by 1814
Abstract
3-(1H,1H,2H,2H-Perfluorooctyl)-1-vinylimidazolium chloride [2126844–17–3], a strong fluorosurfactant with remarkably high solubility in water, was expediently converted into the respective doubly NHC-complexed silver salt with nitrate as counter ion in quantitative yield. Due to its vinyl substituents, [...] Read more.
3-(1H,1H,2H,2H-Perfluorooctyl)-1-vinylimidazolium chloride [2126844–17–3], a strong fluorosurfactant with remarkably high solubility in water, was expediently converted into the respective doubly NHC-complexed silver salt with nitrate as counter ion in quantitative yield. Due to its vinyl substituents, [bis(3-(1H,1H,2H,2H-perfluorooctyl)-1-vinylimidazol-2-ylidene)silver(I)] nitrate, Ag(FNHC)2NO3, represents a polymerizable N-heterocyclic carbene transfer reagent, thus potentially offering simple and robust access to coordination polymers with crosslinking metal bridges. The compound was characterized by infrared and NMR spectroscopy, mass spectrometry as well as elemental analysis, and supplemented by X-ray single-crystal structure determination. It crystallizes in the monoclinic crystal system in the space group P21/c. With 173.3°, the geometry of the Ag-carbene bridge deviates slightly from linearity. The disordered perfluoroalkyl side chains exhibit a helical conformation. Full article
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13 pages, 1389 KiB  
Article
Design and Synthesis of C-1 Methoxycarbonyl Derivative of Narciclasine and Its Biological Activity
by Lihi Habaz, Korey Bedard, Mitchell Smith, Liqin Du, Alexander Kornienko and Tomas Hudlicky
Molecules 2022, 27(12), 3809; https://doi.org/10.3390/molecules27123809 - 14 Jun 2022
Cited by 1 | Viewed by 2003
Abstract
A 15-step chemoenzymatic total synthesis of C-1 methoxycarbonyl narciclasine (10) was accomplished. The synthesis began with the toluene dioxygenase-mediated dihydroxylation of ortho-dibromobenzene to provide the corresponding cis-dihydrodiol (12) as a single enantiomer. Further key steps included a [...] Read more.
A 15-step chemoenzymatic total synthesis of C-1 methoxycarbonyl narciclasine (10) was accomplished. The synthesis began with the toluene dioxygenase-mediated dihydroxylation of ortho-dibromobenzene to provide the corresponding cis-dihydrodiol (12) as a single enantiomer. Further key steps included a nitroso Diels–Alder reaction and an intramolecular Heck cyclization. The C-1 homolog 10 was tested and evaluated for antiproliferative activity against natural narciclasine (1) as the positive control. Experimental and spectral data are reported for all novel compounds. Full article
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13 pages, 3064 KiB  
Article
Generation and Reactions of ε-Carbonyl Cations via Group 13 Catalysis
by Page M. Penner and James R. Green
Molecules 2022, 27(10), 3078; https://doi.org/10.3390/molecules27103078 - 11 May 2022
Viewed by 1417
Abstract
The generation of ε-carbonyl cations and their reactions with nucleophiles is accomplished readily without transition metal cation stabilization, using the ε-bromide dienoate or dienone starting materials and GaCl3 or InCl3 catalysis. Arene nucleophiles are somewhat more straightforward than allyltrimethylsilane, but allyltrimethylsilane [...] Read more.
The generation of ε-carbonyl cations and their reactions with nucleophiles is accomplished readily without transition metal cation stabilization, using the ε-bromide dienoate or dienone starting materials and GaCl3 or InCl3 catalysis. Arene nucleophiles are somewhat more straightforward than allyltrimethylsilane, but allyltrimethylsilane and propiophenone trimethysilyl enol ether each react successfully with InCl3 catalysis. The viability of these cations is supported by DFT calculations. Full article
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18 pages, 10293 KiB  
Article
New Ceramics Precursors Containing Si and Ge Atoms—Cubic Germasilsesquioxanes—Synthesis, Thermal Decomposition and Spectroscopic Analysis
by Aleksandra Skoczeń, Dawid Frąckowiak, Robert E. Przekop, Miłosz Frydrych, Małgorzata Kasperkowiak, Piotr Jeleń, Maciej Sitarz and Bogdan Marciniec
Molecules 2022, 27(4), 1441; https://doi.org/10.3390/molecules27041441 - 21 Feb 2022
Cited by 4 | Viewed by 2482
Abstract
Compounds of the silsesquioxane type are attractive material precursors. High molecular weights and well-defined structures predestine them to create ceramics with a controlled composition at the molecular level. New molecular precursors of ceramic materials with the ratio of Si:Ge = 7:1 atoms were [...] Read more.
Compounds of the silsesquioxane type are attractive material precursors. High molecular weights and well-defined structures predestine them to create ceramics with a controlled composition at the molecular level. New molecular precursors of ceramic materials with the ratio of Si:Ge = 7:1 atoms were obtained. The influence of organic substituents on the thermal decomposition processes of germasilsesquioxanes was investigated. Some of the structures obtained are characterized by a high non-volatile residue after the thermal decomposition process. The introduction of the germanium atom to the structure of the silsesquioxane molecular cage reduces the thermal stability of the obtained structures. Full article
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20 pages, 1950 KiB  
Article
Transition Metal-Free Synthesis of Halobenzo[b]furans from O-Aryl Carbamates via o-Lithiation Reactions
by Claudia Feberero, Cintia Virumbrales, Carlos Sedano, Lorena Renedo, Samuel Suárez-Pantiga and Roberto Sanz
Molecules 2022, 27(2), 525; https://doi.org/10.3390/molecules27020525 - 14 Jan 2022
Cited by 3 | Viewed by 1836
Abstract
A straightforward and transition metal-free one-pot protocol to synthesize halobenzo[b]furans has been developed employing simple and easily available starting materials such as O-aryl carbamates and alkynylsulfones. The fine-tuning of the different steps involved was key to achieving a successful one-pot [...] Read more.
A straightforward and transition metal-free one-pot protocol to synthesize halobenzo[b]furans has been developed employing simple and easily available starting materials such as O-aryl carbamates and alkynylsulfones. The fine-tuning of the different steps involved was key to achieving a successful one-pot procedure. Initially, a directed ortho-lithiation process, which uses the carbamate as the directed metalation group, was crucial in providing access to O-2-alkynylaryl N,N-diethyl carbamates by a direct alkynylation of the o-lithiated carbamate, with arylsulfonylalkynes as electrophilic reagents. Cyclization of the generated o-alkynylaryl carbamates was successfully accomplished through a strategy involving in situ carbamate alkaline hydrolysis under conventional heating or microwave irradiation, coupled with a subsequent heterocyclization step delivering the desired benzo[b]furans. A wide variety of new halobenzo[b]furans has been synthesized and their utility has been demonstrated by their further transformation. Full article
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13 pages, 4419 KiB  
Communication
Synthesis and Biological Activity of 3-(Heteroaryl)quinolin-2(1H)-ones Bis-Heterocycles as Potential Inhibitors of the Protein Folding Machinery Hsp90
by Enrique L. Larghi, Alexandre Bruneau, Félix Sauvage, Mouad Alami, Juliette Vergnaud-Gauduchon and Samir Messaoudi
Molecules 2022, 27(2), 412; https://doi.org/10.3390/molecules27020412 - 9 Jan 2022
Cited by 8 | Viewed by 2233
Abstract
In the context of our SAR study concerning 6BrCaQ analogues as C-terminal Hsp90 inhibitors, we designed and synthesized a novel series of 3-(heteroaryl)quinolin-2(1H), of types 3, 4, and 5, as a novel class of analogues. A Pd-catalyzed Liebeskind–Srogl [...] Read more.
In the context of our SAR study concerning 6BrCaQ analogues as C-terminal Hsp90 inhibitors, we designed and synthesized a novel series of 3-(heteroaryl)quinolin-2(1H), of types 3, 4, and 5, as a novel class of analogues. A Pd-catalyzed Liebeskind–Srogl cross-coupling was developed as a convenient approach for easy access to complex purine architectures. This series of analogues showed a promising biological effect against MDA-MB231 and PC-3 cancer cell lines. This study led to the identification of the best compounds, 3b (IC50 = 28 µM) and 4e, which induce a significant decrease of CDK-1 client protein and stabilize the levels of Hsp90 and Hsp70 without triggering the HSR response. Full article
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15 pages, 1756 KiB  
Article
Stereoselective Synthesis of δ- and ε-Amino Ketone Derivatives from N-tert-Butanesulfinyl Aldimines and Functionalized Organolithium Compounds
by Ana Sirvent, Francisco Foubelo and Miguel Yus
Molecules 2021, 26(21), 6503; https://doi.org/10.3390/molecules26216503 - 28 Oct 2021
Cited by 3 | Viewed by 2132
Abstract
The addition of functionalized organolithium compounds derived from 5-chloro-2-methoxy-1-pentene and 6-chloro-2-methoxy-1-hexene to N-tert-butanesulfinyl aldimines imines, and a subsequent hydrolysis of the enol ether moiety, yielded different δ- and ε-amino ketone derivatives, respectively, in moderate yields and diastereoselectivities. The application of [...] Read more.
The addition of functionalized organolithium compounds derived from 5-chloro-2-methoxy-1-pentene and 6-chloro-2-methoxy-1-hexene to N-tert-butanesulfinyl aldimines imines, and a subsequent hydrolysis of the enol ether moiety, yielded different δ- and ε-amino ketone derivatives, respectively, in moderate yields and diastereoselectivities. The application of these compounds in organic synthesis was demonstrated by the preparation of 2-substituted 6-methylpiperidines in a stereoselective manner, among them natural alkaloids (+)- and (−)-isosolenopsin A. Full article
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33 pages, 12753 KiB  
Article
Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties
by Mohamed Yacine Ameur Messaoud, Ghenia Bentabed-Ababsa, Ziad Fajloun, Monzer Hamze, Yury S. Halauko, Oleg A. Ivashkevich, Vadim E. Matulis, Thierry Roisnel, Vincent Dorcet and Florence Mongin
Molecules 2021, 26(20), 6314; https://doi.org/10.3390/molecules26206314 - 19 Oct 2021
Cited by 1 | Viewed by 2358
Abstract
Five protocols were first compared for the copper-catalyzed C-N bond formation between 7-azaindole and aryl/heteroaryl iodides/bromides. The 1-arylated 7-azaindoles thus obtained were subjected to deprotometalation-iodolysis sequences using lithium 2,2,6,6-tetramethylpiperidide as the base and the corresponding zinc diamide as an in situ trap. The [...] Read more.
Five protocols were first compared for the copper-catalyzed C-N bond formation between 7-azaindole and aryl/heteroaryl iodides/bromides. The 1-arylated 7-azaindoles thus obtained were subjected to deprotometalation-iodolysis sequences using lithium 2,2,6,6-tetramethylpiperidide as the base and the corresponding zinc diamide as an in situ trap. The reactivity of the substrate was discussed in light of the calculated atomic charges and the pKa values. The behavior of the 1-arylated 7-azaindoles in direct iodination was then studied, and the results explained by considering the HOMO orbital coefficients and the atomic charges. Finally, some of the iodides generated, generally original, were involved in the N-arylation of indole. While crystallographic data were collected for fifteen of the synthesized compounds, biological properties (antimicrobial, antifungal and antioxidant activity) were evaluated for others. Full article
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Review

Jump to: Research

29 pages, 26357 KiB  
Review
The Choice of Rhodium Catalysts in [2+2+2] Cycloaddition Reaction: A Personal Account
by Anna Pla-Quintana and Anna Roglans
Molecules 2022, 27(4), 1332; https://doi.org/10.3390/molecules27041332 - 16 Feb 2022
Cited by 13 | Viewed by 2654
Abstract
[2+2+2] Cycloaddition reaction is a captivating process that assembles six-membered rings from three unsaturations with complete atom economy. Of the multiple transition metals that can be used to catalyze this reaction, rhodium offers many advantages. These include high activity and versatility, but especially [...] Read more.
[2+2+2] Cycloaddition reaction is a captivating process that assembles six-membered rings from three unsaturations with complete atom economy. Of the multiple transition metals that can be used to catalyze this reaction, rhodium offers many advantages. These include high activity and versatility, but especially the ability to easily tune the reactivity and selectivity by the modification of the ligands around the metal. In this personal account, we summarize our endeavours in the development of efficient and sustainable [2+2+2] cycloaddition reactions to prepare products of interest, develop conditions in which the catalyst can be recovered and reused, and understand the mechanistic details that govern the selectivity of the processes. Full article
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38 pages, 16300 KiB  
Review
Regioselective C-H Functionalization of the Six-Membered Ring of the 6,5-Fused Heterocyclic Systems: An Overview
by Soukaina Faarasse, Nabil El Brahmi, Gérald Guillaumet and Saïd El Kazzouli
Molecules 2021, 26(19), 5763; https://doi.org/10.3390/molecules26195763 - 23 Sep 2021
Cited by 6 | Viewed by 3319
Abstract
The regioselective C-H functionalization of the five-membered ring of the 6,5-fused heterocyclic systems is nowadays well documented due to its high reactivity compared to the six-membered ring. So, developing new procedures of C-H functionalization of the six-membered ring “by thinking out of the [...] Read more.
The regioselective C-H functionalization of the five-membered ring of the 6,5-fused heterocyclic systems is nowadays well documented due to its high reactivity compared to the six-membered ring. So, developing new procedures of C-H functionalization of the six-membered ring “by thinking out of the box” is extremely challenging, which explains the limited number of reports published to date. This review paper aims to highlight advances achieved in this emerging chemistry research and discusses recently reported methods. Full article
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