Pub Date : 2025-03-10DOI: 10.1021/acs.orglett.5c00465
Xiangkai Kong, Ming-Bai Gou, Bo Li, Zhen-Qi Luo, Yu Su, Yi Li, Chao Yang, Bin Liu, Qing He, Jiang-Fei Li, Jiquan Zhang, Jianta Wang, Lei Tang, Rong-Hua Wang
The transition-metal-catalyzed ring-opening functionalization of aziridines presents a promising approach for synthesizing structurally complex amines. However, the rearranged functionalization of aziridines poses significant challenges. Herein, we report the first rearranged alkenylation of aziridines with aryl alkenes via Ni–Brønsted acid co-catalysis, leading to the rapid synthesis of a diverse array of allylamines with yields reaching up to 91%. Mechanistic studies suggest that the reaction occurs through the rearrangement of aziridine to generate an imine intermediate. This intermediate is subsequently captured by an alkene under nickel catalysis, ultimately leading to the formation of allylamines.
{"title":"Nickel-Catalyzed Rearranged Alkenylation of 2-Arylaziridines with Aryl Alkenes to Access Allylamines","authors":"Xiangkai Kong, Ming-Bai Gou, Bo Li, Zhen-Qi Luo, Yu Su, Yi Li, Chao Yang, Bin Liu, Qing He, Jiang-Fei Li, Jiquan Zhang, Jianta Wang, Lei Tang, Rong-Hua Wang","doi":"10.1021/acs.orglett.5c00465","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00465","url":null,"abstract":"The transition-metal-catalyzed ring-opening functionalization of aziridines presents a promising approach for synthesizing structurally complex amines. However, the rearranged functionalization of aziridines poses significant challenges. Herein, we report the first rearranged alkenylation of aziridines with aryl alkenes via Ni–Brønsted acid co-catalysis, leading to the rapid synthesis of a diverse array of allylamines with yields reaching up to 91%. Mechanistic studies suggest that the reaction occurs through the rearrangement of aziridine to generate an imine intermediate. This intermediate is subsequently captured by an alkene under nickel catalysis, ultimately leading to the formation of allylamines.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"14 40 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143582956","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-10DOI: 10.1021/acs.orglett.5c00111
Yuko Bando, Martin Klapper, Rosa Herbst, Anna Sachse, Pierre Stallforth, Hans-Dieter Arndt
The total synthesis of Pseudomonas-derived cyclic lipodepsipeptide anikasin was achieved. Using a depsipeptide building block and balanced protecting groups on the branching d-allo-Thr residue, the synthesis was established semiautomatically on a synthesizer. Buffered deprotections minimized side reactions and afforded synthetic anikasin and its enantiomer. Biological activity studies indicated that anikasin’s mode of action is directly resulting from its physicochemical properties.
{"title":"Semiautomated Total Synthesis of the Cyclic Lipodepsipeptide Anikasin","authors":"Yuko Bando, Martin Klapper, Rosa Herbst, Anna Sachse, Pierre Stallforth, Hans-Dieter Arndt","doi":"10.1021/acs.orglett.5c00111","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00111","url":null,"abstract":"The total synthesis of <i>Pseudomonas</i>-derived cyclic lipodepsipeptide anikasin was achieved. Using a depsipeptide building block and balanced protecting groups on the branching <span>d</span>-<i>allo</i>-Thr residue, the synthesis was established semiautomatically on a synthesizer. Buffered deprotections minimized side reactions and afforded synthetic anikasin and its enantiomer. Biological activity studies indicated that anikasin’s mode of action is directly resulting from its physicochemical properties.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"29 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143582952","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-10DOI: 10.1021/acs.orglett.5c00271
Pan-Pan Li, Zhi Yang, Shao-Qun Cai, Wu Liang, Shi-Cui Fang, Jun-Fei Zhao, Bin Pan, Fei Du
A general and efficient method for the direct alkynylation and oxidation of remote C(sp3)–H bonds under photoirradiation is described. In this reaction, the Pd catalyst acts as both a photocatalyst to generate the nitrogen radical and a cross-coupling catalyst with a terminal alkyne. Attractive features of this system include good functional group tolerance, scalability, convenient reagents, and an operating system. The utility of this protocol is highlighted by its application for derivatization of several valuable aza-heterocycles such as caspase-3 inhibitor and azepinone derivatives.
{"title":"Palladium-Catalyzed and Photoinduced Site-Selective Alkynylation and Oxidation of the Remote C(sp3)–H","authors":"Pan-Pan Li, Zhi Yang, Shao-Qun Cai, Wu Liang, Shi-Cui Fang, Jun-Fei Zhao, Bin Pan, Fei Du","doi":"10.1021/acs.orglett.5c00271","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00271","url":null,"abstract":"A general and efficient method for the direct alkynylation and oxidation of remote C(sp<sup>3</sup>)–H bonds under photoirradiation is described. In this reaction, the Pd catalyst acts as both a photocatalyst to generate the nitrogen radical and a cross-coupling catalyst with a terminal alkyne. Attractive features of this system include good functional group tolerance, scalability, convenient reagents, and an operating system. The utility of this protocol is highlighted by its application for derivatization of several valuable aza-heterocycles such as caspase-3 inhibitor and azepinone derivatives.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"132 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143582953","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A palladium/norbornene (NBE)-catalyzed 2-fold C–H/C–X coupling reaction of aryl iodides is reported. Bromine-substituted benzimidazoles were chosen as electrophilic and termination reagents, and the versatile polycyclic aromatic hydrocarbon products were successfully obtained. The strategy overcomes the challenge of catalyst poisoning by heterocyclic substrates. In addition, the imidazole moiety in the product is endowed with a localization role, thus enabling the compounds to be applied in a wider synthetic scenario, and the fluorescence persisted. Furthermore, the bioactivity evaluation has identified three promising leading compounds 3b, 4e, and 4i.
{"title":"Palladium/Norbornene Cooperative Catalysis 2-Fold C–H/C–X Coupling: Construction of Polycyclic Aromatic Hydrocarbons from Brominated Benzimidazoles","authors":"Ming-Xuan Wang, Yi-Ming Li, Wei Zeng, Ming-Yao Zhang, Wen-Zhou Yu, Ze-Hui Zheng, Yuan-Yuan Sun, Jin-Heng Li, Yan-Ping Zhu","doi":"10.1021/acs.orglett.5c00298","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00298","url":null,"abstract":"A palladium/norbornene (NBE)-catalyzed 2-fold C–H/C–X coupling reaction of aryl iodides is reported. Bromine-substituted benzimidazoles were chosen as electrophilic and termination reagents, and the versatile polycyclic aromatic hydrocarbon products were successfully obtained. The strategy overcomes the challenge of catalyst poisoning by heterocyclic substrates. In addition, the imidazole moiety in the product is endowed with a localization role, thus enabling the compounds to be applied in a wider synthetic scenario, and the fluorescence persisted. Furthermore, the bioactivity evaluation has identified three promising leading compounds <b>3b</b>, <b>4e</b>, and <b>4i</b>.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"56 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143582954","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-10DOI: 10.1021/acs.orglett.5c00806
Argha Saha, Emanuele Casali, Ankan Ghosh, Debabrata Maiti
The synthesis of bioactive oxazoles is often inefficient, and the reported methods remain largely unexplored for complex derivatives. To circumvent this issue, we have utilized a metal-free, photomediated [3 + 2] cycloaddition reaction between diazo compounds and nitriles, leading to a step- and reagent-economical synthesis of bioactive oxazoles. These exciting developments guided us in the efficient synthesis of oxazole-based natural products like annuloline, alkaloids like pimprinethine, labradorin 2, and oxazole-containing pharmaceuticals such as oxaprozin. Utilizing this approach, we have also demonstrated efficient synthesis of deuterium-labeled and heterocyclic-based oxazoles.
{"title":"Modular Approach for Photoinduced Cycloaddition Enabling the Synthesis of Diverse Bioactive Oxazoles","authors":"Argha Saha, Emanuele Casali, Ankan Ghosh, Debabrata Maiti","doi":"10.1021/acs.orglett.5c00806","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00806","url":null,"abstract":"The synthesis of bioactive oxazoles is often inefficient, and the reported methods remain largely unexplored for complex derivatives. To circumvent this issue, we have utilized a metal-free, photomediated [3 + 2] cycloaddition reaction between diazo compounds and nitriles, leading to a step- and reagent-economical synthesis of bioactive oxazoles. These exciting developments guided us in the efficient synthesis of oxazole-based natural products like annuloline, alkaloids like pimprinethine, labradorin 2, and oxazole-containing pharmaceuticals such as oxaprozin. Utilizing this approach, we have also demonstrated efficient synthesis of deuterium-labeled and heterocyclic-based oxazoles.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"1 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143582962","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-10DOI: 10.1021/acs.orglett.5c00300
Chi Gao, Ru Zhong Zhang, Mang Wang
Ring-fluorinated azaheterocycles have wide applications in agrochemicals, pharmaceuticals, and synthesis, which prompt continuous endeavors to expand such heterocyclic families. However, monofluorinated triazaheterocycles have hardly been explored. This work reported a novel and modular synthesis of monofluorinated 1,2,4-triazoles and 1,3,5-triazines, which utilizes N-CF3 imidoyl chlorides as unique polyfluoro synthons and their defluorinative annulations with hydrazines/imidazines. Further modifications of these fluorinated heterocycles highlight the potential of the method for accessing functional molecules.
{"title":"Modular Synthesis of Monofluorinated 1,2,4-Triazoles/1,3,5-Triazines via Defluorinative Annulations of N-CF3 Imidoyl Chlorides","authors":"Chi Gao, Ru Zhong Zhang, Mang Wang","doi":"10.1021/acs.orglett.5c00300","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00300","url":null,"abstract":"Ring-fluorinated azaheterocycles have wide applications in agrochemicals, pharmaceuticals, and synthesis, which prompt continuous endeavors to expand such heterocyclic families. However, monofluorinated triazaheterocycles have hardly been explored. This work reported a novel and modular synthesis of monofluorinated 1,2,4-triazoles and 1,3,5-triazines, which utilizes <i>N</i>-CF<sub>3</sub> imidoyl chlorides as unique polyfluoro synthons and their defluorinative annulations with hydrazines/imidazines. Further modifications of these fluorinated heterocycles highlight the potential of the method for accessing functional molecules.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"91 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143582955","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-10DOI: 10.1021/acs.orglett.5c00506
He Li, Baoheng Wu, Tao Chen, Shuai Yang, Wangze Li, Shunling Cao, Zhishuang Du, Ye Lu, Ning Xu, Xinxin Jin, Jiaqi Yu, Jinglin Liu
A Rh(III)-catalyzed C–H cascade annulation reaction of benzamidine hydrochlorides with iodonium ylides has been successfully accomplished, providing an efficient strategy for the synthesis of various 1-aminoisoquinoline derivatives in moderate to good yields. Here, iodonium ylide serves as an accessible and safe carbene precursor. Further derivatizations were implemented to demonstrate the potential utility of this cascade annulation reaction. Furthermore, the photophysical properties of these compounds may have potential applications in photoelectric materials.
{"title":"Synthesis of 1-Aminoisoquinolines via Rh(III)-Catalyzed C–H Cascade Annulation of Benzamidines with Iodonium Ylides","authors":"He Li, Baoheng Wu, Tao Chen, Shuai Yang, Wangze Li, Shunling Cao, Zhishuang Du, Ye Lu, Ning Xu, Xinxin Jin, Jiaqi Yu, Jinglin Liu","doi":"10.1021/acs.orglett.5c00506","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00506","url":null,"abstract":"A Rh(III)-catalyzed C–H cascade annulation reaction of benzamidine hydrochlorides with iodonium ylides has been successfully accomplished, providing an efficient strategy for the synthesis of various 1-aminoisoquinoline derivatives in moderate to good yields. Here, iodonium ylide serves as an accessible and safe carbene precursor. Further derivatizations were implemented to demonstrate the potential utility of this cascade annulation reaction. Furthermore, the photophysical properties of these compounds may have potential applications in photoelectric materials.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"36 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143583053","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Vinyl sulfonates are vital intermediates in organic synthesis, serving as versatile electrophiles in various cross-coupling reactions. Despite their significance, direct methods for synthesizing vinyl sulfonates from styrenes have been limited. In this study, we introduce an innovative electrochemical approach that leverages bromine radical mediation to facilitate the direct synthesis of vinyl sulfonates, cheap nBu4NBr acts as both an electrolyte and a catalytic amount. This process involves the reaction of styrenes with sodium sulfinates and water under electrochemical conditions, offering a straightforward pathway to these compounds. The developed strategy is characterized by its high efficiency, operational simplicity, and environmentally benign nature, adhering to the principles of green chemistry while ensuring high atom economy and remarkable regioselectivity. Furthermore, this methodology proves effective for gram-scale synthesis and allows for the subsequent functionalization of vinyl sulfonate products with pharmaceutical derivatives, thus broadening the potential applications of electrochemical techniques in styrene functionalization.
{"title":"Electrochemical Synthesis of Vinyl Sulfonates Mediated by Bromine Radicals","authors":"Yu-Da Huang, Yu-Yuan Zhang, Yu-Jing Zhou, Rui Xue, Guo-Ao Wang, Fei-Hu Cui, Xiu-Jin Meng, Mao-Rui Wang, Ying-Ming Pan, Hai-Tao Tang","doi":"10.1021/acs.orglett.5c00562","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00562","url":null,"abstract":"Vinyl sulfonates are vital intermediates in organic synthesis, serving as versatile electrophiles in various cross-coupling reactions. Despite their significance, direct methods for synthesizing vinyl sulfonates from styrenes have been limited. In this study, we introduce an innovative electrochemical approach that leverages bromine radical mediation to facilitate the direct synthesis of vinyl sulfonates, cheap <i>n</i>Bu<sub>4</sub>NBr acts as both an electrolyte and a catalytic amount. This process involves the reaction of styrenes with sodium sulfinates and water under electrochemical conditions, offering a straightforward pathway to these compounds. The developed strategy is characterized by its high efficiency, operational simplicity, and environmentally benign nature, adhering to the principles of green chemistry while ensuring high atom economy and remarkable regioselectivity. Furthermore, this methodology proves effective for gram-scale synthesis and allows for the subsequent functionalization of vinyl sulfonate products with pharmaceutical derivatives, thus broadening the potential applications of electrochemical techniques in styrene functionalization.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"2018 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143582958","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
α-Chloroboronic esters are a class of stable multifunctional molecules that show unique applications in pharmaceutical science and organic chemistry. Despite their apparent utility, the synthetic methods of these compounds remain limited. Herein, a novel strategy for the efficient synthesis of α-chloroboronic esters is developed via photoredox-catalyzed chloro-alkoxycarbonylation of vinyl boronic esters. This strategy features the advantages of high atom economy, environmental friendliness, and excellent functional group compatibility and was verified by the cross-coupling of a variety of free alcohols, oxalyl chlorides, and vinyl boronic esters. Control experiments and mechanistic studies indicate that the alkoxycarbonyl radical and α-boryl carbocation are key intermediates in this transformation.
{"title":"Synthesis of α-Chloroboronic Esters via Photoredox-Catalyzed Chloro-Alkoxycarbonylation of Vinyl Boronic Esters","authors":"Wen-Duo Li, Na-Na Wei, Nan Feng, Tian-Ye Zheng, Wen-Wen Hao, Guozhe Guo, Xiaoqin Niu, Chao Kong, Chao Shuai, Hui Wen, Yingying Li, Kejian Chang, Zhi-Jun Li","doi":"10.1021/acs.orglett.5c00402","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00402","url":null,"abstract":"α-Chloroboronic esters are a class of stable multifunctional molecules that show unique applications in pharmaceutical science and organic chemistry. Despite their apparent utility, the synthetic methods of these compounds remain limited. Herein, a novel strategy for the efficient synthesis of α-chloroboronic esters is developed via photoredox-catalyzed chloro-alkoxycarbonylation of vinyl boronic esters. This strategy features the advantages of high atom economy, environmental friendliness, and excellent functional group compatibility and was verified by the cross-coupling of a variety of free alcohols, oxalyl chlorides, and vinyl boronic esters. Control experiments and mechanistic studies indicate that the alkoxycarbonyl radical and α-boryl carbocation are key intermediates in this transformation.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"19 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143582961","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-08DOI: 10.1021/acs.orglett.4c04868
Sonali Kukreja, Abhishek Kumar Yadav, Vikas D. Ghule, Srinivas Dharavath
In this study, we synthesized energetic materials integrating thiadiazole and triazole moieties. The newly developed compounds were thoroughly characterized using NMR, IR, elemental analysis, TGA-DSC, and single-crystal X-ray diffraction (for compound 3). These compounds exhibited acceptable properties, including high densities (1.88–1.92 g cm–3), moderate to good detonation performance (VOD: 6383–8128 m s–1), good thermal stability (143–238 °C), and less sensitivity to impact (>15 J) and friction (360 N). Notably, compounds 4 and 8 achieved superior detonation velocities compared to nearly all reported sulfur-based energetic materials to date. This work highlights the significance of triazole-thiadiazole frameworks in the development and fine-tuning of energetic materials.
{"title":"Employing Nitrogen–Sulfur Synergy: 1,2,3-Triazole-Thiadiazole-Based Energetic Materials","authors":"Sonali Kukreja, Abhishek Kumar Yadav, Vikas D. Ghule, Srinivas Dharavath","doi":"10.1021/acs.orglett.4c04868","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04868","url":null,"abstract":"In this study, we synthesized energetic materials integrating thiadiazole and triazole moieties. The newly developed compounds were thoroughly characterized using NMR, IR, elemental analysis, TGA-DSC, and single-crystal X-ray diffraction (for compound <b>3</b>). These compounds exhibited acceptable properties, including high densities (1.88–1.92 g cm<sup>–3</sup>), moderate to good detonation performance (VOD: 6383–8128 m s<sup>–1</sup>), good thermal stability (143–238 °C), and less sensitivity to impact (>15 J) and friction (360 N). Notably, compounds <b>4</b> and <b>8</b> achieved superior detonation velocities compared to nearly all reported sulfur-based energetic materials to date. This work highlights the significance of triazole-thiadiazole frameworks in the development and fine-tuning of energetic materials.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"29 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143575127","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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