Asian Journal of Organic Chemistry最新文献_第6页

Reversal of Regioselectivity in the Nucleophilic Fluorination of 1,2-Dimesylate with Potassium Fluoride and 18-Crown-6 1,2-二甲基磺酸与氟化钾和18-冠-6亲核氟化反应的区域选择性逆转

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-06-29 DOI: 10.1002/ajoc.202500481

Eloah P. Ávila, Karla L. Lopes, Mauro V. de Almeida, Josefredo R. Pliego

{"title":"Reversal of Regioselectivity in the Nucleophilic Fluorination of 1,2-Dimesylate with Potassium Fluoride and 18-Crown-6","authors":"Eloah P. Ávila, Karla L. Lopes, Mauro V. de Almeida, Josefredo R. Pliego","doi":"10.1002/ajoc.202500481","DOIUrl":"10.1002/ajoc.202500481","url":null,"abstract":"The control of chemoselectivity and regioselectivity in chemical reactions is a crucial area of research, focused on achieving the desired product with high yield. An example is the selective monofluorination of vicinal dimesylates, which can open a route for the synthesis of β-fluoroamines, β-fluorohydrins, and alkenyl fluorides. This study examined the reactivity of a terminal vicinal dimesylate with potassium fluoride and 18-crown-6 through experimental methods and theoretical calculations. We found an unexpected higher reactivity of the dimesylate toward a nucleophilic substitution on the C2 carbon rather than C1 carbon. In addition, the SN2 product is favored over E2. Extensive theoretical calculations using conformational sampling were done to understand this preferential reaction pathway. Our findings show that electrostatic interactions between the oxygen of the vicinal dimesylate and the potassium ion in the KF(18-crown-6) complex favor SN2 at C2 over C1 and also enhance selectivity for SN2 over E2. In addition, one hydrogen of CH3 in the vicinal mesylated group interacts with the incoming fluoride ion, favoring SN2 and E2 reactions involving C1 and C2, while reducing E2 products involving C3. Our results open an avenue for exploring this selectivity, which can be useful for further functionalization.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://aces.onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202500481","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057775","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Click Chemistry-Enabled Synthesis of Diversely Functionalized Cyclobutenes 点击化学合成不同功能化环丁烯

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-06-27 DOI: 10.1002/ajoc.202500525

Dr. Christopher J. Smedley

{"title":"Click Chemistry-Enabled Synthesis of Diversely Functionalized Cyclobutenes","authors":"Dr. Christopher J. Smedley","doi":"10.1002/ajoc.202500525","DOIUrl":"10.1002/ajoc.202500525","url":null,"abstract":"4-Membered rings are important structural motifs in many bioactive natural products and pharmaceutically relevant molecules. Further, these strained ring systems serve as versatile precursors for accessing diverse classes of organic compounds. In this study, 1,1-bis(fluorosulfonyl)-2-(pyridin-1-ium-1-yl)ethan-1-ide, a stable ethene-1,1-disulfonyl fluoride precursor, is applied to expand the library of highly functionalized cyclobutenes accessible through a [2 + 2] click chemistry cycloaddition pathway. The 29 cyclobutene products were isolated in perfect regioselectivity influenced by the choice of electron-withdrawing (ester, ketone, sulfone, and sulfonyl fluoride) or electron-donating groups (chalcogen) on the alkyne, significantly broadening the accessibility of these valuable four-membered ring systems. The reaction is straightforward to perform, tolerates a wide variety of functional groups, uses mild reaction conditions and requires minimal purification. The potential to diversify the cyclobutene core is demonstrated through sulfur-fluoride exchange (SuFEx) click chemistry and amide coupling reactions.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://aces.onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202500525","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057846","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Recent Advances in the Trifluoromethylselenofunctionalization of C─C Multiple Bonds: Synthesis of Vicinally Functionalized CF3Se-Containing Compounds C─C多键三氟甲基硒化的新进展：邻功能化含cf3se化合物的合成

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-06-27 DOI: 10.1002/ajoc.202500553

Ying Chen, Kanta Pajujantaro, Gong-Qing Liu

{"title":"Recent Advances in the Trifluoromethylselenofunctionalization of C─C Multiple Bonds: Synthesis of Vicinally Functionalized CF3Se-Containing Compounds","authors":"Ying Chen, Kanta Pajujantaro, Gong-Qing Liu","doi":"10.1002/ajoc.202500553","DOIUrl":"10.1002/ajoc.202500553","url":null,"abstract":"The incorporation of the trifluoromethylselenyl (CF3Se) group has become a prominent area of research in recent years because of its high electron-withdrawing capacity, excellent lipophilicity, good stability, and favorable bioavailability. These properties make CF3Se a promising structural motif for drug design and development. Among the various methods for synthesizing CF3Se-containing compounds, trifluoromethylselenofunctionalization of unsaturated C─C bonds has emerged as a powerful strategy for the preparation of these compounds because this process facilitates the introduction of the CF3Se motif as well as other functional groups into unsaturated C─C bonds. In this review, we summarize recent advancements and achievements in the trifluoromethylselenofunctionalization of multiple C─C bonds. For clarity, the reactions were classified according to the type of functional groups introduced. Additionally, this review highlights the mechanistic aspects of these reactions, which may inspire further work in this appealing research field.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 8","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144833360","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Strategic Advances in the Total Syntheses of Opioids: Codeine, Morphine, and Related Alkaloids 阿片类药物：可待因、吗啡及相关生物碱的全合成研究进展

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-06-27 DOI: 10.1002/ajoc.202500333

Dr. Ayan Mondal, Abhishek Mondal, Satadru Dutta, Prof. Dr. Alakesh Bisai

引用次数: 0

Plantacare 2000: A Biosurfactant for an Eco-Friendly Palladium Catalyzed Cyanation of Aromatic Bromides 生态友好型钯催化芳烃氰化的生物表面活性剂

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-06-27 DOI: 10.1002/ajoc.202500513

Simone Zurzolo, Elena Ermini, Erica Locatelli, Elena Petricci, Giuseppina I. Truglio, Luigi Vaccaro, Federica Valentini, Maurizio Taddei

{"title":"Plantacare 2000: A Biosurfactant for an Eco-Friendly Palladium Catalyzed Cyanation of Aromatic Bromides","authors":"Simone Zurzolo, Elena Ermini, Erica Locatelli, Elena Petricci, Giuseppina I. Truglio, Luigi Vaccaro, Federica Valentini, Maurizio Taddei","doi":"10.1002/ajoc.202500513","DOIUrl":"10.1002/ajoc.202500513","url":null,"abstract":"We introduce here Plantacare 2000 (PL-2000), a renewable biosurfactant for sustainable palladium-catalysed cyanation reactions in water. PL-2000 is derived from plant-based raw materials, is fully biodegradable, nontoxic to the aquatic environment and commercially available without the need for complex synthesis. It represents a safer alternative for Pd-catalysed cyanation reactions using K4[Fe(CN)6], while maintaining acceptable synthetic efficiency and a wide substrate scope. PL-2000 proved to be superior to PEG-based surfactants in terms of environmental compatibility and retention of surfactant properties at high temperatures (cloud point > 100 °C). It is also compatible with microwave heating (MW) for challenging substrates. The approach eliminates the need for deoxygenation processes and the use of organic co-solvents and limits the use of additives. Analysis of green chemistry metrics shows that this method achieves an optimal balance between efficiency and environmental impact compared to existing alternatives. The results show that PL-2000 is a promising alternative for surfactant-assisted, metal-catalysed reactions in aqueous media and paves the way for more environmentally friendly synthetic transformations.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://aces.onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202500513","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057845","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Photo- and Electroluminescence of N,N-Diphenylaminophenyl–Quinoxaline Donor–Acceptor-Type Dyes: Electronic Impacts of Electron-Withdrawing Ability of the Acceptor Unit N，N-二苯基氨基苯基喹啉给受体型染料的光致发光和电致发光：受体单元吸电子能力的电子影响

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-06-25 DOI: 10.1002/ajoc.202500364

Masaki Nagaoka, Keito Ueda, Hiroaki Chihara, Prof. Dr. Naoya Suzuki, Prof. Dr. Shintaro Kodama, Prof. Dr. Takeshi Maeda, Prof. Dr. Shigeyuki Yagi

{"title":"Photo- and Electroluminescence of N,N-Diphenylaminophenyl–Quinoxaline Donor–Acceptor-Type Dyes: Electronic Impacts of Electron-Withdrawing Ability of the Acceptor Unit","authors":"Masaki Nagaoka, Keito Ueda, Hiroaki Chihara, Prof. Dr. Naoya Suzuki, Prof. Dr. Shintaro Kodama, Prof. Dr. Takeshi Maeda, Prof. Dr. Shigeyuki Yagi","doi":"10.1002/ajoc.202500364","DOIUrl":"10.1002/ajoc.202500364","url":null,"abstract":"Organic light-emitting diodes (OLEDs) based on thermally activated delayed fluorescence (TADF) are expected as next-generation electroluminescent devices because they provide high device performance due to utilization of both singlet and triplet excitons. Here we report the development of intramolecular charge transfer dyes with a compact N,N-diphenylaminophenyl–quinoxaline donor–acceptor system for use as TADF emitters; namely, 4-(3-methylquinoxalin-2-yl)-N,N-diphenylaniline (1a), N,N-diphenyl-4-(3-(trifluoromethyl)quinoxalin-2-yl)aniline (1b), and 4-(6,7-difluoro-3-(trifluoromethyl)quinoxalin-2-yl)-N,N-diphenylaniline (1c). Dye 1a exhibited fluorescence at 464 nm in poly(methyl methacrylate) film. In contrast, introducing trifluoromethyl and/or fluoro groups to the quinoxaline skeleton resulted in red-shifted emission at 516 and 539 nm for 1b and 1c, respectively. These red shifts were predominantly induced by stabilization of the LUMO energy levels, and interestingly, 1b and 1c had higher photoluminescence (PL) quantum yields under nitrogen atmosphere than those under aerobic conditions. From the temperature dependence of the PL intensity and PL lifetimes, it was found that 1b and 1c exhibited TADF properties, although 1a showed only prompt fluorescence. We successfully fabricated a solution-processed OLED with 1c as an emitter. The device exhibited yellowish green electroluminescence, and the maximum external quantum yield of 3.02% indicated a relatively small contribution of TADF to overall electroluminescence.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 8","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://aces.onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202500364","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144833328","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Anti-Markovnikov Reactions via Visible Light Photocatalysis 可见光催化下的反马氏反应

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-06-25 DOI: 10.1002/ajoc.202500396

Vishal Srivastava, Shraddha Tivari, Pravin K. Singh, Praveen P. Singh

引用次数: 0

Microwave-Assisted Rapid and Efficient Synthesis of Novel Indazole-Based 1,3,4-Oxadiazole Derivatives with Molecular Docking, ADME, and DFT Studies 微波辅助下新型吲哚基1,3,4-恶二唑衍生物的分子对接、ADME和DFT研究

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-06-23 DOI: 10.1002/ajoc.202500111

Bandaru Gopi, Vijayaparthasarathi Vijayakumar

{"title":"Microwave-Assisted Rapid and Efficient Synthesis of Novel Indazole-Based 1,3,4-Oxadiazole Derivatives with Molecular Docking, ADME, and DFT Studies","authors":"Bandaru Gopi, Vijayaparthasarathi Vijayakumar","doi":"10.1002/ajoc.202500111","DOIUrl":"10.1002/ajoc.202500111","url":null,"abstract":"A novel and efficient synthetic protocol has been developed for the preparation of indazole-1,3,4-oxadiazoles through microwave-assisted reactions, using both aromatic and aliphatic carboxylic acids as starting materials. The structural identification and purity of the synthesized compounds were confirmed using IR, ¹H NMR, ¹3C NMR, and HRMS spectral data. Additionally, their photophysical properties were characterized using ultraviolet–visible (UV–vis) and fluorescence spectroscopy to determine the absorption maxima and emission wavelengths. Among the synthesized derivatives, four compounds 8h, 8l, 13c, and 13d that exhibited the least energy band gaps were selected for detailed computational analysis using DFT. TD-DFT calculations were conducted to predict the theoretical UV–vis absorption spectra, which were then compared with experimental data, including molar extinction coefficients, Stokes shifts, and fluorescence quantum yields. Molecular docking studies were performed using AutoDock Version 1.5.6, along with structural data from the protein data bank (PDB ID: 4EJN), to evaluate the binding affinities of all derivatives. Compounds 8h, 8j, 13h, and 13j showed the most favorable binding energies. Finally, the pharmacokinetic and drug-likeness profiles of the compounds were evaluated using the SWISS ADME platform, which provided insights into their physicochemical properties and visualized gastrointestinal absorption and blood–brain barrier permeability through the BOILED-Egg predictive model.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 8","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144832944","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Light-Mediated Decomposition of Arylseleninic Acids in Aqueous Medium: A Green Alternative Toward Organoselenium-Functionalized Imidazo[1,2-a]pyridines 光介导的芳基亚硒酸在水介质中的分解：有机硒功能化咪唑[1,2- A]吡啶的绿色替代品

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-06-21 DOI: 10.1002/ajoc.202500442

Caroline S. Gomes, Carolina A. de Oliveira, João M. Anghinoni, Sabrina S. Ferreira, Prof. Márcio S. Silva, Prof. Filipe Penteado, Prof. Eder J. Lenardão

{"title":"Light-Mediated Decomposition of Arylseleninic Acids in Aqueous Medium: A Green Alternative Toward Organoselenium-Functionalized Imidazo[1,2-a]pyridines","authors":"Caroline S. Gomes, Carolina A. de Oliveira, João M. Anghinoni, Sabrina S. Ferreira, Prof. Márcio S. Silva, Prof. Filipe Penteado, Prof. Eder J. Lenardão","doi":"10.1002/ajoc.202500442","DOIUrl":"10.1002/ajoc.202500442","url":null,"abstract":"In the present work, a mild protocol was developed to construct 2-aryl-3-(arylselanyl)imidazo[1,2-a]pyridines, under blue light irradiation, employing benzeneseleninic acid derivatives as a Se(II) source. The experimental design approach (design of experiment, DoE) was used to establish the best reaction conditions, which delivered fourteen derivatives in moderate to good yields (23%–75%), after reacting for 24–48 h. Furthermore, the developed method proved to be efficient when increasing the reaction scale (2.5 mmol), which provided the desired product in 70% yield (0.61 g) after 24 h of reaction, demonstrating the applicability of this method on a preparative scale. The present approach does not require the use of metals, strong oxidants, or heating, in addition to producing only H2O and diaryl diselenide as byproducts, which can be recovered and reused.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 8","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://aces.onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202500442","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144833350","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Microwave-Assisted Metal-Free Synthesis of Vinyl Sulfoxides Using DMSO as Solvent and Reagent 以DMSO为溶剂和试剂的微波辅助无金属合成乙烯基亚砜

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-06-21 DOI: 10.1002/ajoc.202500210

Desai Bhavyesh, Arti Ramani, Monak Patel, Akshay Bharodiya, Sudha Soliya, Kishor Padala, Togati Naveen

{"title":"Microwave-Assisted Metal-Free Synthesis of Vinyl Sulfoxides Using DMSO as Solvent and Reagent","authors":"Desai Bhavyesh, Arti Ramani, Monak Patel, Akshay Bharodiya, Sudha Soliya, Kishor Padala, Togati Naveen","doi":"10.1002/ajoc.202500210","DOIUrl":"10.1002/ajoc.202500210","url":null,"abstract":"Among organosulfur compounds, sulfoxides play a crucial role in many biologically active substances with a diverse range of applications in natural products, pharmaceuticals, agrochemicals, and materials. We have developed an efficient microwave-assisted method for synthesizing vinyl sulfoxides through oxidative condensation of easily accessible aromatic aldehydes or benzyl alcohols with dimethyl sulfoxide (DMSO), using a base under ambient conditions. In this method, DMSO serves a dual purpose: it acts as a source of the (methylsulfinyl)methyl group (─CH₂SOMe) and functions as a solvent. This protocol is highly tolerant of various aromatic aldehydes, including heteroaryl and α,β-unsaturated aldehydes, yielding corresponding vinyl sulfoxides in good to excellent yields. Additionally, this methodology can also be applied to synthesize various vinyl sulfoxides from benzyl alcohols, yielding moderate to good results. The advantages of this strategy include being metal-free, requiring short reaction times, maintaining mild conditions, operational simplicity, high selectivity, and achieving moderate to excellent yields.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057952","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0