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Keywords = nitroalkene

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15 pages, 1994 KiB  
Article
Modeling of the General Trends of Reactivity and Regioselectivity in Cyclopentadiene–Nitroalkene Diels–Alder Reactions
by Adrianna Fałowska, Stanisław Grzybowski, Daniel Kapuściński, Karol Sambora and Agnieszka Łapczuk
Molecules 2025, 30(11), 2467; https://doi.org/10.3390/molecules30112467 - 4 Jun 2025
Cited by 1 | Viewed by 1132
Abstract
This study presents a theoretical investigation of the electronic properties of mono- and pentasubstituted cyclopentadiene analogs and variously substituted conjugated nitroalkenes bearing electron-donating and electron-withdrawing groups. Conceptual Density Functional Theory (CDFT) and Electron Localization Function (ELF) analyses were employed to characterize the global [...] Read more.
This study presents a theoretical investigation of the electronic properties of mono- and pentasubstituted cyclopentadiene analogs and variously substituted conjugated nitroalkenes bearing electron-donating and electron-withdrawing groups. Conceptual Density Functional Theory (CDFT) and Electron Localization Function (ELF) analyses were employed to characterize the global and local reactivity indices of the reactants. The obtained data provided insights into the nucleophilic and electrophilic nature of the investigated systems, allowing for the prediction of their reactivity patterns in Diels–Alder reactions. A reactivity model for conjugated alkenes toward cyclopentadienes was developed based on correlation analysis using Hammett substituent constants. This approach enabled the prediction of reaction polarity in (4+2) cycloaddition processes, providing insight into how the electronic effects of substituents influence the reaction course. These findings contribute to a deeper understanding of structure–reactivity relationships in Diels–Alder processes. Full article
(This article belongs to the Special Issue Cyclization Reactions in Organic Synthesis: Recent Developments)
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18 pages, 2229 KiB  
Article
The Puzzle of the New Type of Intermediate in the Course of [2 + 2] Cycloaddition with the Participation of Conjugated Nitroalkenes: MEDT Computational Study
by Radomir Jasiński and Agnieszka Kącka-Zych
Molecules 2025, 30(11), 2410; https://doi.org/10.3390/molecules30112410 - 30 May 2025
Viewed by 675
Abstract
The phenomena of regio- and stereoselectivity and the molecular mechanism of the [2 + 2] cycloaddition reaction between (E)-2-arylnitroethenes and the ynamine molecular system were analyzed using wb97xd/6-311 + G(d) (PCM) quantumchemical calculations. It was found that, independently of the stepwise nature of [...] Read more.
The phenomena of regio- and stereoselectivity and the molecular mechanism of the [2 + 2] cycloaddition reaction between (E)-2-arylnitroethenes and the ynamine molecular system were analyzed using wb97xd/6-311 + G(d) (PCM) quantumchemical calculations. It was found that, independently of the stepwise nature of the cycloaddition, the full retention of the stereoconfiguration of the nitroalkene can be interpreted and explained. Next, the analysis of the electronic properties of the localized reaction intermediate suggests its possible zwitterionic nature. Additionally, the solvent and the substituent effect on the reaction course were also evaluated. In consequence, the proposed mechanism can be treated as general for some groups of [2 + 2] cycloaddition processes. Lastly, for the model process, the full Bonding Evolution Theory (BET) analysis along the reaction coordinate was performed. It was found that the [2 + 2] cycloaddition reaction between (E)-2-phenylonitroethene and ynamine begins with the formation of two pseudoradical centers at the C2 and C3 atoms. First, a C2-C3 single bond is formed in phase V by combining two pseudoradical centers, while the formation of a second C4-C1 single bond begins at the last, eleventh phase of the reaction path. A BET analysis of intermediate (I) allows it to be classified as a compound with a pseudoradical structure. Next to zwitterions and biradicals, it is evidently new type of intermediate on the path of the [2 + 2] cycloaddition reaction. Full article
(This article belongs to the Section Organic Chemistry)
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25 pages, 5183 KiB  
Article
A Comprehensive Study of the Synthesis, Spectral Characteristics, Quantum–Chemical Molecular Electron Density Theory, and In Silico Future Perspective of Novel CBr3-Functionalyzed Nitro-2-Isoxazolines Obtained via (3 + 2) Cycloaddition of (E)-3,3,3-Tribromo-1-Nitroprop-1-ene
by Karolina Zawadzińska-Wrochniak, Karolina Kula, Mar Ríos-Gutiérrez, Bartłomiej Gostyński, Tomasz Krawczyk and Radomir Jasiński
Molecules 2025, 30(10), 2149; https://doi.org/10.3390/molecules30102149 - 13 May 2025
Cited by 1 | Viewed by 883
Abstract
The search for new heterocyclic compounds with biological potential is one of the current challenges in modern chemistry. Therefore, the comprehensive study of (3 + 2) cycloaddition (32CA) reactions between a series of aryl-substituted nitrile N-oxides (NOs) and (E)-3,3,3-tribromo-1-nitroprop-1-ene (TBNP) is [...] Read more.
The search for new heterocyclic compounds with biological potential is one of the current challenges in modern chemistry. Therefore, the comprehensive study of (3 + 2) cycloaddition (32CA) reactions between a series of aryl-substituted nitrile N-oxides (NOs) and (E)-3,3,3-tribromo-1-nitroprop-1-ene (TBNP) is carried out. According to the experimental research, in all tested 32CAs, the proper (4RS,5RS)-3-aryl-4-nitro-5-tribromomethyl-2-isoxazolines are obtained as only one reaction product. In turn, the quantum–chemical MEDT study shows that the creation of heterocycles occur via the polar attack of zwitterionic moderate-nucleophilic NOs to strong electrophilic TBNP. The reactions are realized according to a two-stage, one-step asynchronous mechanism, in which the formation of the O-C(CBr3) bond takes place once the C-C(NO2) bond is already formed. What is more, the computational analysis confirmed the experimental results. At the end, the obtained 2-isoxazolines were docked to three proteins: gelatinase B, cyclooxygenase COX-1, and Caspase-7. We hope that the presented study will be helpful for searching for the future direction of application for this class of organic compounds. Full article
(This article belongs to the Special Issue Methods and Applications of Cycloaddition Reactions)
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20 pages, 5554 KiB  
Article
Syn-Propanethial S-Oxide as an Available Natural Building Block for the Preparation of Nitro-Functionalized, Sulfur-Containing Five-Membered Heterocycles: An MEDT Study
by Mikołaj Sadowski, Ewa Dresler, Karolina Zawadzińska, Aneta Wróblewska and Radomir Jasiński
Molecules 2024, 29(20), 4892; https://doi.org/10.3390/molecules29204892 - 15 Oct 2024
Cited by 11 | Viewed by 2260
Abstract
The regio- and stereoselectivity and the molecular mechanisms of the [3 + 2] cycloaddition reactions between Syn-propanethial S-oxide and selected conjugated nitroalkenes were explored theoretically in the framework of the Molecular Electron Density Theory. It was found that cycloadditions with the participation [...] Read more.
The regio- and stereoselectivity and the molecular mechanisms of the [3 + 2] cycloaddition reactions between Syn-propanethial S-oxide and selected conjugated nitroalkenes were explored theoretically in the framework of the Molecular Electron Density Theory. It was found that cycloadditions with the participation of nitroethene as well as its methyl- and chloro-substituted analogs can be realized via a single-step mechanism. On the other hand, [3 + 2] cycloaddition reactions between Syn-propanethial S-oxide and 1,1-dinitroethene can proceed according to a stepwise mechanism with a zwitterionic intermediate. Finally, we evaluated the affinity of model reaction products for several target proteins: cytochrome P450 14α-sterol demethylase CYP51 (RSCB Database PDB ID: 1EA1), metalloproteinase gelatinase B (MMP-9; PDB ID: 4XCT), and the inhibitors of cyclooxygenase COX-1 (PDB:3KK6) and COX-2 (PDB:5KIR). Full article
(This article belongs to the Special Issue Heterocyclic Compounds: Synthesis, Application and Theoretical Study)
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17 pages, 8670 KiB  
Article
A New Insight into the Molecular Mechanism of the Reaction between 2-Methoxyfuran and Ethyl (Z)-3-phenyl-2-nitroprop-2-enoate: An Molecular Electron Density Theory (MEDT) Computational Study
by Mikołaj Sadowski, Ewa Dresler, Aneta Wróblewska and Radomir Jasiński
Molecules 2024, 29(20), 4876; https://doi.org/10.3390/molecules29204876 - 14 Oct 2024
Cited by 7 | Viewed by 1726
Abstract
The molecular mechanism of the reaction between 2-methoxyfuran and ethyl (Z)-3-phenyl-2-nitroprop-2-enoate was investigated using wb97xd/6-311+G(d,p)(PCM) quantum chemical calculations. It was found that the most probable reaction mechanism is fundamentally different from what was previously postulated. In particular, six possible zwitterionic intermediates [...] Read more.
The molecular mechanism of the reaction between 2-methoxyfuran and ethyl (Z)-3-phenyl-2-nitroprop-2-enoate was investigated using wb97xd/6-311+G(d,p)(PCM) quantum chemical calculations. It was found that the most probable reaction mechanism is fundamentally different from what was previously postulated. In particular, six possible zwitterionic intermediates were detected on the reaction pathway. Their formation is determined by the nature of local nucleophile/electrophile interactions. Additionally, the channel involving the formation of the exo-nitro Diels–Alder cycloadduct was completely ruled out. Finally, the electronic nature of the five- and six-membered nitronates as potential TACs was evaluated. Full article
(This article belongs to the Special Issue Multiconfigurational and DFT Methods Applied to Chemical Systems—2nd Edition)
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10 pages, 2578 KiB  
Communication
Aminocyclopropenium as a New Class of Hydrogen Bonding Catalyst in Friedel–Crafts Alkylation
by Xuesuo Ma, Jiaxi Xu, Jingjing Liu, Jun He, Tong Chang, Qingbiao Yang, Ning Li, Dong Qian and Zhenjiang Li
Catalysts 2023, 13(10), 1370; https://doi.org/10.3390/catal13101370 - 16 Oct 2023
Cited by 1 | Viewed by 2096
Abstract
H-bonding has achieved massive advancements by utilizing an H-bond donor (HBD) to interact with the electron-rich site of the substrate, and an H-bond acceptor (HBA) to coordinate with the electron-deficient site. Rapid transformation is often correlated with the acidity of HBD, namely the [...] Read more.
H-bonding has achieved massive advancements by utilizing an H-bond donor (HBD) to interact with the electron-rich site of the substrate, and an H-bond acceptor (HBA) to coordinate with the electron-deficient site. Rapid transformation is often correlated with the acidity of HBD, namely the degree of charge deficiency of the hydrogen proton. In addition, the positive cations were employed to enhance the HBD; the electron-withdrawing groups were also a dissimilar approach for increasing the capability of the H-bond donor. We first introduced the H-bonding organic ion pair tris(phenylamino)cyclopropenium (TPAC·Cl) into the Friedel–Crafts alkylation of indoles with nitroalkenes, which was implemented via vicinal positive charges on the cyclopropenium core. The counter ion chloride anion became a potential HBA to activate the electron-deficient part of the substrate. X-ray analyses of a single crystal of TPAC·Cl described the 3D architecture and the delocalized cationic charge in the solid state. The aromatic cyclopropenium endowed the N–H moieties with the ability of the H-bond donor to activate the nitroalkene; meanwhile, the chloride anion acted as the H-bond acceptor to activate the indole. The amino-cyclopropenium-offered HBD and HBA displayed cooperative organocatalysis in the Friedel–Crafts alkylation of indole with nitroalkene. A new class of hydrogen bonding catalysis and a working mechanism were proposed. Full article
(This article belongs to the Special Issue Organocatalysis in the Chemical Transformations, 2nd Edition)
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13 pages, 2671 KiB  
Article
Understanding the Molecular Mechanism of Thermal and LA-Catalysed Diels–Alder Reactions between Cyclopentadiene and Isopropyl 3-Nitroprop-2-Enate
by Ewa Dresler, Aneta Wróblewska and Radomir Jasiński
Molecules 2023, 28(14), 5289; https://doi.org/10.3390/molecules28145289 - 8 Jul 2023
Cited by 19 | Viewed by 1722
Abstract
The molecular mechanism of the Diels–Alder reaction with the participation of cyclopentadiene and isopropyl 3-nitroprop-2-enate was examined based on wb97xd/6-311+G(d) (PCM) quantum chemical calculations. It was found that the type of mechanism for the conversion of addends depends significantly on the reaction conditions. [...] Read more.
The molecular mechanism of the Diels–Alder reaction with the participation of cyclopentadiene and isopropyl 3-nitroprop-2-enate was examined based on wb97xd/6-311+G(d) (PCM) quantum chemical calculations. It was found that the type of mechanism for the conversion of addends depends significantly on the reaction conditions. In less-polar environments, a one-step polar mechanism is realised. In more polar solvents, the formation of “extended”-type zwitterionic intermediates is possible. In contrast, in the presence of an LA-type catalyst, the one-step mechanisms are replaced by respective stepwise mechanisms with zwitterionic or heterocyclic intermediates. Full article
(This article belongs to the Special Issue Computational and Theoretical Studies on Isomeric Organic Compounds)
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15 pages, 2663 KiB  
Article
Fully Selective Synthesis of Spirocyclic-1,2-oxazine N-Oxides via Non-Catalysed Hetero Diels-Alder Reactions with the Participation of Cyanofunctionalysed Conjugated Nitroalkenes
by Przemysław Woliński, Agnieszka Kącka-Zych, Aneta Wróblewska, Ewelina Wielgus, Rafał Dolot and Radomir Jasiński
Molecules 2023, 28(12), 4586; https://doi.org/10.3390/molecules28124586 - 6 Jun 2023
Cited by 16 | Viewed by 2677
Abstract
Hetero Diels-Alder (HDA) reactions with the participation of E-2-aryl-1-cyano-1-nitroethenes and methylenecyclopentane were evaluated on the basis of experimental as well as quantumchemical data. It was found that contrary to most known HDA reactions, title processes are realised under non-catalytic conditions and with full [...] Read more.
Hetero Diels-Alder (HDA) reactions with the participation of E-2-aryl-1-cyano-1-nitroethenes and methylenecyclopentane were evaluated on the basis of experimental as well as quantumchemical data. It was found that contrary to most known HDA reactions, title processes are realised under non-catalytic conditions and with full regiocontrol. The DFT study shows, without any doubt, the polar but single-step reaction mechanism. Deeper exploration using Bonding Evolution Theory (BET) techniques gives a clear image of the sequences of electron density reorganisation along the reaction coordinate. The first C4-C5 bond is created in phase VII by merging two monosynaptic basins, while the second O1-C6 bond is created in the last phase by a donation of the nonbonding electron density of O1 to C6. Based on the research, we can conclude that the analysed reaction proceeds according to a two-stage one-step mechanism. Full article
(This article belongs to the Special Issue Recent Progress in Heteroorganic Chemistry)
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11 pages, 2336 KiB  
Article
Full Regio- and Stereoselective Protocol for the Synthesis of New Nicotinoids via Cycloaddition Processes with the Participation of Trans-Substituted Nitroethenes: Comprehensive Experimental and MEDT Study
by Jowita Kras, Przemysław Woliński, Roman Nagatsky, Oleg M. Demchuk and Radomir Jasiński
Molecules 2023, 28(8), 3535; https://doi.org/10.3390/molecules28083535 - 17 Apr 2023
Cited by 6 | Viewed by 1686
Abstract
[3 + 2] Cycloaddition reactions with the participation of Z-C-(3-pyridyl)-N-methylnitrone and series of E-2-R-nitroethenes were both experimentally and theoretically explored in the framework of Molecular Electron Density Theory. It was found that all considered processes are realized under mild [...] Read more.
[3 + 2] Cycloaddition reactions with the participation of Z-C-(3-pyridyl)-N-methylnitrone and series of E-2-R-nitroethenes were both experimentally and theoretically explored in the framework of Molecular Electron Density Theory. It was found that all considered processes are realized under mild conditions and in full regio- and stereocontrol. The ELF analysis additionally showed that the studied reaction proceeds by a two-stage, one-step mechanism. Full article
(This article belongs to the Special Issue Synthesis of Heterocyclic Compounds via Cycloadditions: Applications in Medicinal Chemistry)
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12 pages, 6172 KiB  
Article
Synthesis of Tetrasubstituted Nitroalkenes and Preliminary Studies of Their Enantioselective Organocatalytic Reduction
by Patricia Camarero González, Sergio Rossi, Miguel Sanz, Francesca Vasile and Maurizio Benaglia
Molecules 2023, 28(7), 3156; https://doi.org/10.3390/molecules28073156 - 1 Apr 2023
Cited by 1 | Viewed by 2396
Abstract
Starting from commercially available ketones, a reproducible and reliable strategy for the synthesis of tetrasubstituted nitroalkenes was successfully developed, using a two-step procedure; the HWE olefination of the ketone to form the corresponding α,β-unsaturated esters is followed by a nitration reaction to introduce [...] Read more.
Starting from commercially available ketones, a reproducible and reliable strategy for the synthesis of tetrasubstituted nitroalkenes was successfully developed, using a two-step procedure; the HWE olefination of the ketone to form the corresponding α,β-unsaturated esters is followed by a nitration reaction to introduce the nitro group in the α position of the ester group. The enantioselective organocatalytic reduction of these compounds has also been preliminarily studied, to access the functionalized enantioenriched nitroalkanes, which are useful starting materials for further synthetic elaborations. The absolute configuration of the reduction product was established by chemical correlation of the chiral nitroalkane with a known product; preliminary DFT calculations were also conducted to rationalize the stereochemical outcome of the organocatalytic enantioselective reduction. Full article
(This article belongs to the Special Issue New Approaches to Synthetic Organic Chemistry)
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21 pages, 1995 KiB  
Article
[3+3]-Annulation of Cyclic Nitronates with Vinyl Diazoacetates: Diastereoselective Synthesis of Partially Saturated [1,2]Oxazino[2,3-b][1,2]oxazines and Their Base-Promoted Ring Contraction to Pyrrolo[1,2-b][1,2]oxazine Derivatives
by Yulia A. Antonova, Yulia V. Nelyubina, Sema L. Ioffe and Andrey A. Tabolin
Molecules 2023, 28(7), 3025; https://doi.org/10.3390/molecules28073025 - 28 Mar 2023
Cited by 4 | Viewed by 3108
Abstract
A rhodium(II)-catalyzed reaction of cyclic nitronates (5,6-dihydro-4H-1,2-oxazine N-oxides) with vinyl diazoacetates proceeds as a [3+3]-annulation producing bicyclic unsaturated nitroso acetals (4a,5,6,7-tetrahydro-2H-[1,2]oxazino[2,3-b][1,2]oxazines). Optimization of reaction conditions revealed the use of Rh(II) octanoate as the preferred catalyst in [...] Read more.
A rhodium(II)-catalyzed reaction of cyclic nitronates (5,6-dihydro-4H-1,2-oxazine N-oxides) with vinyl diazoacetates proceeds as a [3+3]-annulation producing bicyclic unsaturated nitroso acetals (4a,5,6,7-tetrahydro-2H-[1,2]oxazino[2,3-b][1,2]oxazines). Optimization of reaction conditions revealed the use of Rh(II) octanoate as the preferred catalyst in THF at room temperature, which allows the preparation of target products in good yields and excellent diastereoselectivity. Under basic conditions, namely, the combined action of DBU and alcohol, these nitroso acetals undergo ring contraction of an unsaturated oxazine ring into the corresponding pyrrole. Both transformations can be performed in a one-pot fashion, thus constituting a quick approach to oxazine-annulated pyrroles from available starting materials, such as nitroalkenes, olefins, and diazo compounds. Full article
(This article belongs to the Special Issue Novelties in N-Heterocycles Chemistry: From Synthesis to Application)
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10 pages, 2854 KiB  
Perspective
Phenyl Formate as a CO Surrogate for the Reductive Cyclization of Organic Nitro Compounds to Yield Different N-Heterocycles: No Need for Autoclaves and Pressurized Carbon Monoxide
by Fabio Ragaini, Francesco Ferretti and Manar Ahmed Fouad
Catalysts 2023, 13(2), 224; https://doi.org/10.3390/catal13020224 - 18 Jan 2023
Cited by 5 | Viewed by 2422
Abstract
The reductive cyclization of different organic nitro compounds by carbon monoxide, catalyzed by transition metal complexes, is a very efficient and clean strategy for the synthesis of many N-heterocycles. However, its use requires the use of autoclaves and pressurized CO lines. In [...] Read more.
The reductive cyclization of different organic nitro compounds by carbon monoxide, catalyzed by transition metal complexes, is a very efficient and clean strategy for the synthesis of many N-heterocycles. However, its use requires the use of autoclaves and pressurized CO lines. In this perspective, the authors will present the results obtained in their laboratories on the use of phenyl formate as a convenient CO surrogate, able to liberate carbon monoxide under the reaction conditions and allowing the use of a cheap glass pressure tube as a reaction vessel. In most cases, yields were better than those previously reported by the use of pressurized CO, proving that the use of CO surrogates can be a viable alternative to the gaseous reagent. Full article
(This article belongs to the Special Issue Exclusive Papers of the Editorial Board Members (EBMs) of Catalysts)
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9 pages, 1317 KiB  
Article
Understanding the Regioselectivity and the Molecular Mechanism of [3 + 2] Cycloaddition Reactions between Nitrous Oxide and Conjugated Nitroalkenes: A DFT Computational Study
by Ewa Dresler, Aneta Wróblewska and Radomir Jasiński
Molecules 2022, 27(23), 8441; https://doi.org/10.3390/molecules27238441 - 2 Dec 2022
Cited by 17 | Viewed by 1980
Abstract
Regiochemical aspects and the molecular mechanism of the [3 + 2] cycloaddition between nitrous oxide and conjugated nitroalkenes were evaluated on the basis of the wb97xd/6-311 + G(d) (PCM) computational study. It was found that, independently of the nature of the nitroalkene, all [...] Read more.
Regiochemical aspects and the molecular mechanism of the [3 + 2] cycloaddition between nitrous oxide and conjugated nitroalkenes were evaluated on the basis of the wb97xd/6-311 + G(d) (PCM) computational study. It was found that, independently of the nature of the nitroalkene, all considered processes are realized via polar, single-step mechanisms. All attempts at the localization of hypothetical zwitterionic intermediates were unsuccessful. Additionally, the DFT computational study suggested that, in the course of the reaction, the formation of respective Δ2-4-nitro-4-R1-5-R2-1-oxa-2,3-diazolines was preferred from the kinetic point of view. Full article
(This article belongs to the Special Issue Five and Six-Membered Heterocyclic Compounds and Their Therapeutic Potential)
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7 pages, 1211 KiB  
Proceeding Paper
Use of Phenyl Formate as a CO Surrogate for the Reductive Cyclization of Organic Nitro Compounds to Yield Different N-Heterocycles: Avoiding the Use of Autoclaves and Pressurized Gases
by Fabio Ragaini, Francesco Ferretti and Manar Ahmed Fouad
Chem. Proc. 2022, 12(1), 85; https://doi.org/10.3390/ecsoc-26-13711 - 18 Nov 2022
Viewed by 1592
Abstract
The reductive cyclization of different organic nitro compounds by carbon monoxide, catalyzed by transition metal complexes, is a very efficient and clean strategy for the synthesis of many N-heterocycles. However, it requires the use of autoclaves and pressurized CO lines. In this [...] Read more.
The reductive cyclization of different organic nitro compounds by carbon monoxide, catalyzed by transition metal complexes, is a very efficient and clean strategy for the synthesis of many N-heterocycles. However, it requires the use of autoclaves and pressurized CO lines. In this paper, the authors will present the results obtained in their laboratories on the use of phenyl formate as a convenient CO surrogate, able to liberate carbon monoxide under reaction conditions and allowing for the use of a cheap glass pressure tube as a reaction vessel. In most cases, yields were better than those previously reported using pressurized CO, proving that the use of CO surrogates can be a viable alternative to the gaseous reagent. Full article
(This article belongs to the Proceedings of The 26th International Electronic Conference on Synthetic Organic Chemistry)
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13 pages, 6084 KiB  
Article
Iridium-Catalyzed and pH-Dependent Reductions of Nitroalkenes to Ketones
by Tingting Wang, Changmeng Liu, Dong Xu, Jiaxi Xu and Zhanhui Yang
Molecules 2022, 27(22), 7822; https://doi.org/10.3390/molecules27227822 - 13 Nov 2022
Cited by 5 | Viewed by 2792
Abstract
A highly chemoselective conversion of α,β-disubstituted nitroalkenes to ketones is developed. An acid-compatible iridium catalyst serves as the key to the conversion. At a 2500 S/C ratio, nitroalkenes were readily converted to ketones in up to 72% isolated yields. A new mechanistic [...] Read more.
A highly chemoselective conversion of α,β-disubstituted nitroalkenes to ketones is developed. An acid-compatible iridium catalyst serves as the key to the conversion. At a 2500 S/C ratio, nitroalkenes were readily converted to ketones in up to 72% isolated yields. A new mechanistic mode involving the reduction of nitroalkene to nitrosoalkene and N-alkenyl hydroxylamine is proposed. This conversion is ready to amplify to a gram-scale synthesis. The pH value plays an indispensable role in controlling the chemoselectivity. Full article
(This article belongs to the Special Issue Catalytic Green Reductions and Oxidations)
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