Pub Date : 2026-02-01Epub Date: 2026-02-25DOI: 10.1002/ajoc.70326
Wen‐Feng Dong , Xinyuan Hu , Jia‐Yi Luo , Zhi Guan , Yan‐Hong He
An environmentally benign electrochemical reductive method has been developed for the hydroselenization/hydrosulfuration of vinyl sulfones with diselenides/disulfides. The reaction proceeds smoothly in an undivided cell at room temperature in open air, without the need for metal catalysts or oxidants, achieving yields of up to 99% for 37 β‐selenosulfones and β‐thiosulfones. This strategy is also applicable to other electron‐deficient olefins, providing a mild and efficient approach for constructing C─Se and C─S bonds.
{"title":"Electroreductive Hydroselenization/Hydrosulfuration of Vinyl Sulfones for the Synthesis of β‐Selenosulfones and β‐Thiosulfones","authors":"Wen‐Feng Dong , Xinyuan Hu , Jia‐Yi Luo , Zhi Guan , Yan‐Hong He","doi":"10.1002/ajoc.70326","DOIUrl":"10.1002/ajoc.70326","url":null,"abstract":"<div><div>An environmentally benign electrochemical reductive method has been developed for the hydroselenization/hydrosulfuration of vinyl sulfones with diselenides/disulfides. The reaction proceeds smoothly in an undivided cell at room temperature in open air, without the need for metal catalysts or oxidants, achieving yields of up to 99% for 37 β‐selenosulfones and β‐thiosulfones. This strategy is also applicable to other electron‐deficient olefins, providing a mild and efficient approach for constructing C─Se and C─S bonds.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 2","pages":"Article e70326"},"PeriodicalIF":2.7,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146224125","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}
Pub Date : 2026-02-01Epub Date: 2026-02-25DOI: 10.1002/ajoc.70327
Qing‐Miao Pu , Bing‐Yu Luo , Xue Ran , Xiao‐Dong Su , Ke‐Jin Jiao , Xiao‐Tong Gao
Herein, a transition metal‐ and oxidant‐free electrochemical method for the direct C3–sulfonylation of imidazo[1,2‐a]pyridines using sulfonyl hydrazides as sulfonylation reagents has been developed. This methodology provides an efficient and practical protocol for the synthesis of 3‐(arylsulfonyl)imidazo[1,2‐a]pyridines, featuring mild reaction conditions, broad substrate scope and enhanced atom economy. Various imidazo[1,2‐a]pyridines and sulfonyl hydrazides could be selectively transformed into the corresponding C3–sulfonylated products in moderate to excellent yields.
{"title":"Electrochemical C3‐Sulfonylation of Imidazo[1,2‐a]pyridines With Sulfonyl Hydrazides","authors":"Qing‐Miao Pu , Bing‐Yu Luo , Xue Ran , Xiao‐Dong Su , Ke‐Jin Jiao , Xiao‐Tong Gao","doi":"10.1002/ajoc.70327","DOIUrl":"10.1002/ajoc.70327","url":null,"abstract":"<div><div>Herein, a transition metal‐ and oxidant‐free electrochemical method for the direct C3–sulfonylation of imidazo[1,2‐<em>a</em>]pyridines using sulfonyl hydrazides as sulfonylation reagents has been developed. This methodology provides an efficient and practical protocol for the synthesis of 3‐(arylsulfonyl)imidazo[1,2‐<em>a</em>]pyridines, featuring mild reaction conditions, broad substrate scope and enhanced atom economy. Various imidazo[1,2‐<em>a</em>]pyridines and sulfonyl hydrazides could be selectively transformed into the corresponding C3–sulfonylated products in moderate to excellent yields.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 2","pages":"Article e70327"},"PeriodicalIF":2.7,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146224336","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}
Pub Date : 2026-02-01Epub Date: 2026-02-25DOI: 10.1002/ajoc.70341
Aditya R. Narnawre , Prashik M. Walke , Prakash D. Shirsath , Nandkishor N. Karade
A mild and efficient oxidative transformation of 2‐alkoxychalcones into unsymmetrical 1,2‐diaryl diketones has been achieved using [(hydroxy)tosyloxyiodo]benzene (HTIB) and catalytic Cu(OTf)2 in acetonitrile at room temperature. The reaction proceeds via a tandem oxidative rearrangement and C─C bond cleavage pathway, delivering diketones in good to excellent yields. The protocol exhibits broad substrate scope and functional group tolerance, with the ortho‐alkoxy group playing a crucial role. The synthetic potential of the obtained 1,2‐diketones is demonstrated by their efficient conversion into densely substituted imidazole and quinoxaline derivatives. A plausible mechanism involving hypervalent iodine‐mediated activation and copper‐assisted oxidation is proposed.
{"title":"Hypervalent Iodine(III)‐Mediated Oxidative Degradation of 2‐Alkoxychalcones Under Copper(II) Catalysis for the Synthesis of Unsymmetrical 1,2‐Diaryl Diketones","authors":"Aditya R. Narnawre , Prashik M. Walke , Prakash D. Shirsath , Nandkishor N. Karade","doi":"10.1002/ajoc.70341","DOIUrl":"10.1002/ajoc.70341","url":null,"abstract":"<div><div>A mild and efficient oxidative transformation of 2‐alkoxychalcones into unsymmetrical 1,2‐diaryl diketones has been achieved using [(hydroxy)tosyloxyiodo]benzene (HTIB) and catalytic Cu(OTf)<sub>2</sub> in acetonitrile at room temperature. The reaction proceeds via a tandem oxidative rearrangement and C─C bond cleavage pathway, delivering diketones in good to excellent yields. The protocol exhibits broad substrate scope and functional group tolerance, with the <em>ortho</em>‐alkoxy group playing a crucial role. The synthetic potential of the obtained 1,2‐diketones is demonstrated by their efficient conversion into densely substituted imidazole and quinoxaline derivatives. A plausible mechanism involving hypervalent iodine‐mediated activation and copper‐assisted oxidation is proposed.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 2","pages":"Article e70341"},"PeriodicalIF":2.7,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147288228","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}
Ligands are the important part of a metal‐catalyzed process. New ligand designing for metal‐catalyzed organic transformations is the focused area of current research. Ligand enabled iron‐catalyzed reactions provide sustainable alternatives to the costly metal‐based methodologies. Furthermore, the one‐pot multicomponent strategies displayed significant attention for the scientific community to access valuable scaffolds. Herein, we have demonstrated new ligand tuned iron‐catalyzed one‐pot multicomponent reactions for the synthesis of diverse heterocyclic scaffolds. New and very simple “nitrogen–oxygen” (“N─O”) type chelating ligands were prepared and applied successfully for the iron‐catalyzed multicomponent cascade reactions enabling the synthesis of diverse heterocyclic scaffolds, including 1,4‐dihydropyridines, 4H‐pyrans, and aminopyrazoles. Prepared ligands as well as all products were well characterized. Mechanistic studies using UV–visible spectroscopy support the in situ formation of the ligand metal complex. The one pot, three component reactions employ readily available aromatic aldehydes and proceed under mild aqueous conditions through sequential carbon carbon bond forming steps, affording the desired heterocycles in good yields with satisfactory selectivity. The methodology also demonstrates good scalability and broad functional group tolerance, recyclable up to five times, underscoring its practical applicability along with green chemistry metrices.
{"title":"Ligand Tuned Reactivity of Iron Catalysts Toward Green Synthesis of 1,4‐Dihydropyridine, 4‐Hydropyran, and Aminopyrazole Derivatives in Aqueous Medium","authors":"Ankit Kachore , Varun Aggarwal , Ekta Bala , Hemant Singh , Manickam Selvaraj , Mohammed A. Assiri , Saima , Rakesh Kumar , Praveen Kumar Verma","doi":"10.1002/ajoc.70321","DOIUrl":"10.1002/ajoc.70321","url":null,"abstract":"<div><div>Ligands are the important part of a metal‐catalyzed process. New ligand designing for metal‐catalyzed organic transformations is the focused area of current research. Ligand enabled iron‐catalyzed reactions provide sustainable alternatives to the costly metal‐based methodologies. Furthermore, the one‐pot multicomponent strategies displayed significant attention for the scientific community to access valuable scaffolds. Herein, we have demonstrated new ligand tuned iron‐catalyzed one‐pot multicomponent reactions for the synthesis of diverse heterocyclic scaffolds. New and very simple “nitrogen–oxygen” (“N─O”) type chelating ligands were prepared and applied successfully for the iron‐catalyzed multicomponent cascade reactions enabling the synthesis of diverse heterocyclic scaffolds, including 1,4‐dihydropyridines, 4H‐pyrans, and aminopyrazoles. Prepared ligands as well as all products were well characterized. Mechanistic studies using UV–visible spectroscopy support the in situ formation of the ligand metal complex. The one pot, three component reactions employ readily available aromatic aldehydes and proceed under mild aqueous conditions through sequential carbon carbon bond forming steps, affording the desired heterocycles in good yields with satisfactory selectivity. The methodology also demonstrates good scalability and broad functional group tolerance, recyclable up to five times, underscoring its practical applicability along with green chemistry metrices.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 2","pages":"Article e70321"},"PeriodicalIF":2.7,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146135816","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}
Pub Date : 2026-02-01Epub Date: 2026-02-25DOI: 10.1002/ajoc.70343
Zixuan Liu , Jiaqi Tong , Bin Liu , Zelong Song , Xingxian Zhang
An efficient electrochemical strategy has been established for the direct selenylation of pyrrolo[2,3‐d] pyrimidine derivatives employing diselenides as the selenium source. This transformation proceeds under catalyst‐ and oxidant‐free conditions, enabling efficient formation of C(sp2)─Se bonds. Moreover, this strategy offers notable advantages including broad substrate scope, good functional group compatibility, high site‐selectivity, and exceptional atom economy. Furthermore, preliminary mechanistic studies suggest that the reaction likely involves radical cation intermediates, which play a key role in promoting the selenylation process.
{"title":"Electrochemical Regioselective C(sp2)–H Selenylation of Pyrrolo[2,3‐d]pyrimidine Derivatives With Diselenides","authors":"Zixuan Liu , Jiaqi Tong , Bin Liu , Zelong Song , Xingxian Zhang","doi":"10.1002/ajoc.70343","DOIUrl":"10.1002/ajoc.70343","url":null,"abstract":"<div><div>An efficient electrochemical strategy has been established for the direct selenylation of pyrrolo[2,3‐<em>d</em>] pyrimidine derivatives employing diselenides as the selenium source. This transformation proceeds under catalyst‐ and oxidant‐free conditions, enabling efficient formation of C(<em>sp</em><sup>2</sup>)─Se bonds. Moreover, this strategy offers notable advantages including broad substrate scope, good functional group compatibility, high site‐selectivity, and exceptional atom economy. Furthermore, preliminary mechanistic studies suggest that the reaction likely involves radical cation intermediates, which play a key role in promoting the selenylation process.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 2","pages":"Article e70343"},"PeriodicalIF":2.7,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147385676","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}
Pub Date : 2026-02-01Epub Date: 2026-02-25DOI: 10.1002/ajoc.70325
Dan Liu , Kaiwen Yi , Shichao Yang , Huanfeng Jiang , Wanqing Wu
A metal‐free photoredox catalysis enabling a decarboxylative radical cascade cyclization for the efficient synthesis of 2‐alkylbenzothiazoles/2‐alkylbenzoselenazoles is described. This protocol utilizes alkyl N‐hydroxyphthalimide (NHPI) esters and 2‐isocyanaryl thioethers/selenoethers as the substrates, and the transformation proceeds through a photoredox‐catalyzed, radical addition‐triggered cascade cyclization. This method features mild conditions, excellent functional group tolerance, and a broad substrate scope encompassing primary, secondary, and tertiary alkyl radicals, providing a versatile entry to these valuable heterocycles.
{"title":"Photoredox‐Catalyzed Decarboxylative Cascade Cyclization of NHPI Esters With Isocyanides: Access to 2‐Alkylbenzothiazoles/2‐Alkylbenzoselenazoles","authors":"Dan Liu , Kaiwen Yi , Shichao Yang , Huanfeng Jiang , Wanqing Wu","doi":"10.1002/ajoc.70325","DOIUrl":"10.1002/ajoc.70325","url":null,"abstract":"<div><div>A metal‐free photoredox catalysis enabling a decarboxylative radical cascade cyclization for the efficient synthesis of 2‐alkylbenzothiazoles/2‐alkylbenzoselenazoles is described. This protocol utilizes alkyl <em>N</em>‐hydroxyphthalimide (NHPI) esters and 2‐isocyanaryl thioethers/selenoethers as the substrates, and the transformation proceeds through a photoredox‐catalyzed, radical addition‐triggered cascade cyclization. This method features mild conditions, excellent functional group tolerance, and a broad substrate scope encompassing primary, secondary, and tertiary alkyl radicals, providing a versatile entry to these valuable heterocycles.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 2","pages":"Article e70325"},"PeriodicalIF":2.7,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146216767","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}
Pub Date : 2026-02-01Epub Date: 2026-02-25DOI: 10.1002/ajoc.70335
Yu‐Chen Wang , Ya‐Chu Yu , Wan‐Hsuan Liu , Niaz Wali , Jiun‐Jie Shie
Pyrimidines are aromatic nitrogen‐containing heterocycles with significant applications in medicinal chemistry and materials science. Conventional two‐step strategies for synthesizing 2,5‐disubstituted pyrimidines from 2,5‐dihalopyrimidines often require toxic reagents, transition metal (TM) catalysts, harsh conditions, specialized substrates, or non‐commercially available reagents. Therefore, this study aims to develop a TM‐free synthetic route for producing 2,5‐disubstituted pyrimidines via heterocyclic skeletal editing. This one‐pot tandem reaction sequence integrates nucleophilic aromatic C─O, C─N, and C─S substitutions with an amidine‐based inverse‐electron demand Diels–Alder reaction, providing efficient synthesis of pyrimidine derivatives in moderate to excellent yields. The modular skeletal editing strategy employs 5‐bromo‐1,2,3‐triazine 1 as a molecular platform, facilitating orthogonal coupling with various phenols, thiophenols, and sodium azide, followed by amidines to achieve skeletal editing under mild conditions using only Cs2CO3. This method offers several advantages, including ready substrate availability, operational simplicity, and high atom economy. To further demonstrate the functional utility of the pyrimidine derivatives, pyrimidine‐based Ru(II) complexes were synthesized for fluorescence imaging in live cells. An alkynylated Ru(II) complex 13 served as a key precursor for the modular incorporation of organelle‐targeting moieties via copper‐catalyzed azide–alkyne cycloaddition. These functionalized metal complexes facilitate selective labeling of the nucleus and mitochondria in live cells.
{"title":"Cs2CO3‐Mediated One‐Pot Orthogonal Reactions of 5‐Bromo‐1,2,3‐Triazine for the Modular Synthesis of Functionalized Pyrimidine Ligands for Metal Complexes in Cellular Imaging","authors":"Yu‐Chen Wang , Ya‐Chu Yu , Wan‐Hsuan Liu , Niaz Wali , Jiun‐Jie Shie","doi":"10.1002/ajoc.70335","DOIUrl":"10.1002/ajoc.70335","url":null,"abstract":"<div><div>Pyrimidines are aromatic nitrogen‐containing heterocycles with significant applications in medicinal chemistry and materials science. Conventional two‐step strategies for synthesizing 2,5‐disubstituted pyrimidines from 2,5‐dihalopyrimidines often require toxic reagents, transition metal (TM) catalysts, harsh conditions, specialized substrates, or non‐commercially available reagents. Therefore, this study aims to develop a TM‐free synthetic route for producing 2,5‐disubstituted pyrimidines via heterocyclic skeletal editing. This one‐pot tandem reaction sequence integrates nucleophilic aromatic C─O, C─N, and C─S substitutions with an amidine‐based inverse‐electron demand Diels–Alder reaction, providing efficient synthesis of pyrimidine derivatives in moderate to excellent yields. The modular skeletal editing strategy employs 5‐bromo‐1,2,3‐triazine <strong>1</strong> as a molecular platform, facilitating orthogonal coupling with various phenols, thiophenols, and sodium azide, followed by amidines to achieve skeletal editing under mild conditions using only Cs<sub>2</sub>CO<sub>3</sub>. This method offers several advantages, including ready substrate availability, operational simplicity, and high atom economy. To further demonstrate the functional utility of the pyrimidine derivatives, pyrimidine‐based Ru(II) complexes were synthesized for fluorescence imaging in live cells. An alkynylated Ru(II) complex <strong>13</strong> served as a key precursor for the modular incorporation of organelle‐targeting moieties via copper‐catalyzed azide–alkyne cycloaddition. These functionalized metal complexes facilitate selective labeling of the nucleus and mitochondria in live cells.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 2","pages":"Article e70335"},"PeriodicalIF":2.7,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147385671","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}
We report a visible‐light‐induced, metal‐free approach to the selective N‐alkylation of quinoxalin‐2(1H)‐ones using aryl diazo esters. This mild, catalyst‐free protocol runs under ambient conditions and allows access to a wide variety of N‐alkylated products with excellent functional group tolerance. Mechanistic studies suggest the formation of a donor–acceptor carbene intermediate that undergoes selective N–H insertion. This study illustrates the usefulness of visible‐light activation of aryl diazo esters and their utilization as alkylating agents to achieve N–H bond functionalization in heterocycles in a sustainable and efficient manner. Density functional theory calculations provide insight into the mechanism and elucidate the role of π−π interactions in facilitating the reaction.
{"title":"Visible‐Light‐Driven N‐Alkylation of Quinoxalin‐2(1H)‐ones With Aryl Diazo Esters","authors":"Sudhir Kumar Hota , Akhilesh Sharma , Anindya Das , Puneet Gupta , Sandip Murarka","doi":"10.1002/ajoc.70313","DOIUrl":"10.1002/ajoc.70313","url":null,"abstract":"<div><div>We report a visible‐light‐induced, metal‐free approach to the selective <em>N</em>‐alkylation of quinoxalin‐2(1<em>H</em>)‐ones using aryl diazo esters. This mild, catalyst‐free protocol runs under ambient conditions and allows access to a wide variety of N‐alkylated products with excellent functional group tolerance. Mechanistic studies suggest the formation of a donor–acceptor carbene intermediate that undergoes selective N–H insertion. This study illustrates the usefulness of visible‐light activation of aryl diazo esters and their utilization as alkylating agents to achieve N–H bond functionalization in heterocycles in a sustainable and efficient manner. Density functional theory calculations provide insight into the mechanism and elucidate the role of π−π interactions in facilitating the reaction.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 2","pages":"Article e70313"},"PeriodicalIF":2.7,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146155278","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}
[8]Circulenes, a class of intriguing polycyclic aromatic hydrocarbons, have garnered considerable attention due to their aesthetically pleasing structures. Despite their unique structural features, the applications of these rigid π‐conjugated systems remain far from fully explored due to the inherent challenges in functionalizing them. In this study, we report the synthesis of a water‐soluble tetrabenzotetraaza[8]circulene derivative (3) through the introduction of four 2,5,8,11‐tetraoxatridecane substituents. The optical properties of 3 were systematically studied in THF/water mixtures, revealing its water‐fraction‐dependent fluorescence. At 77 K, compound 3 exhibits distinctive phosphorescence with an exceptionally long lifetime of 2.08 s and a phosphorescence quantum yield of 12.3%, both among the highest values of reported hetero[8]circulenes. Additionally, 3 displays a pronounced yellow‐green afterglow luminescence that persists for 7.6 s, underscoring its potential for persistent emission applications. This study presents an effective method to modulate the optoelectronic properties of hetero[8]circulene derivatives, offering new opportunities for hetero[8]circulenes as promising functional materials.
{"title":"Synthesis and Photophysical Properties of a Water‐Soluble Tetrabenzotetraaza[8]Circulene Derivative With Long Lifetime Phosphorescence","authors":"Li Jiang , Shijun Gu , Rashid Valiev , Glib Baryshnikov , Fengkun Chen","doi":"10.1002/ajoc.70318","DOIUrl":"10.1002/ajoc.70318","url":null,"abstract":"<div><div>[8]Circulenes, a class of intriguing polycyclic aromatic hydrocarbons, have garnered considerable attention due to their aesthetically pleasing structures. Despite their unique structural features, the applications of these rigid π‐conjugated systems remain far from fully explored due to the inherent challenges in functionalizing them. In this study, we report the synthesis of a water‐soluble tetrabenzotetraaza[8]circulene derivative (<strong>3</strong>) through the introduction of four 2,5,8,11‐tetraoxatridecane substituents. The optical properties of <strong>3</strong> were systematically studied in THF/water mixtures, revealing its water‐fraction‐dependent fluorescence. At 77 K, compound <strong>3</strong> exhibits distinctive phosphorescence with an exceptionally long lifetime of 2.08 s and a phosphorescence quantum yield of 12.3%, both among the highest values of reported hetero[8]circulenes. Additionally, <strong>3</strong> displays a pronounced yellow‐green afterglow luminescence that persists for 7.6 s, underscoring its potential for persistent emission applications. This study presents an effective method to modulate the optoelectronic properties of hetero[8]circulene derivatives, offering new opportunities for hetero[8]circulenes as promising functional materials.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 2","pages":"Article e70318"},"PeriodicalIF":2.7,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146129741","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}
Pub Date : 2026-02-01Epub Date: 2026-02-25DOI: 10.1002/ajoc.70336
Xiaohua Wang , Mingze Wu , Xuerong Chen , Yalan Feng , Yirong Zhou
Trifluoromethylated internal alkynes are presented as a class of versatile building blocks for efficient assembly of various trifluoromethyl group‐containing useful organic molecules through either direct nucleophilic addition or cyclization. Therefore, it has attracted significant attention from organic synthetic chemists and tremendous efforts have been devoted to the development of its rapid preparation. In this review, we aim to provide a comprehensive summary of the latest advances in the straightforward preparation of trifluoromethylated internal alkynes. We would also like to spur the recent discoveries and developments of innovative reaction paradigms in this field. Additionally, crucial challenges and future perspectives on this hot topic are also discussed, with the wish to provide a profound insight for not only future organofluorine chemistry but also fluorine‐containing pharmaceutical science. This manuscript mainly focuses on the direct synthetic methodology to construct various unsymmetrical trifluoromethylated internal alkynes, and it is categorized according to various synthetic methods as well as different types of trifluoromethyl source.
{"title":"A Comprehensive Review for the Straightforward Preparation of Trifluoromethylated Internal Alkynes","authors":"Xiaohua Wang , Mingze Wu , Xuerong Chen , Yalan Feng , Yirong Zhou","doi":"10.1002/ajoc.70336","DOIUrl":"10.1002/ajoc.70336","url":null,"abstract":"<div><div>Trifluoromethylated internal alkynes are presented as a class of versatile building blocks for efficient assembly of various trifluoromethyl group‐containing useful organic molecules through either direct nucleophilic addition or cyclization. Therefore, it has attracted significant attention from organic synthetic chemists and tremendous efforts have been devoted to the development of its rapid preparation. In this review, we aim to provide a comprehensive summary of the latest advances in the straightforward preparation of trifluoromethylated internal alkynes. We would also like to spur the recent discoveries and developments of innovative reaction paradigms in this field. Additionally, crucial challenges and future perspectives on this hot topic are also discussed, with the wish to provide a profound insight for not only future organofluorine chemistry but also fluorine‐containing pharmaceutical science. This manuscript mainly focuses on the direct synthetic methodology to construct various unsymmetrical trifluoromethylated internal alkynes, and it is categorized according to various synthetic methods as well as different types of trifluoromethyl source.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 2","pages":"Article e70336"},"PeriodicalIF":2.7,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146217227","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}
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