Asian Journal of Organic Chemistry最新文献

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Visible-Light-Driven Photoredox [2 + 1] Cycloaddition of Sulfoxonium Ylides With Alkenes 亚砜鎓化物与烯烃的可见光驱动光氧化还原[2 + 1]环加成
IF 2.3 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-09-30 DOI: 10.1002/ajoc.70558
Sibiao Xu, Ning Xian, Dong-Fang Jiang, Huawen Huang
{"title":"Visible-Light-Driven Photoredox [2 + 1] Cycloaddition of Sulfoxonium Ylides With Alkenes","authors":"Sibiao Xu,&nbsp;Ning Xian,&nbsp;Dong-Fang Jiang,&nbsp;Huawen Huang","doi":"10.1002/ajoc.70558","DOIUrl":"https://doi.org/10.1002/ajoc.70558","url":null,"abstract":"<div>\u0000 \u0000 <p>Cyclopropane motifs are widely found in pharmaceuticals, natural products, and functional materials; however, current synthetic methods are often limited by harsh conditions and the requirement for precious metal catalysts. Herein, we have developed a visible‑light‑driven photoredox [2 + 1] cycloaddition strategy, which generates reactive carbon‑centered radicals via single‑electron oxidation of sulfoxonium ylides, followed by an S<sub>N</sub>2 process to achieve cyclopropanation of alkenes. This method requires neither metal catalysts nor additives, and features mild conditions, good substrate compatibility for activated alkenes and various sulfoxonium ylides, and operational simplicity, offering a complementary approach to traditional methods and paving a new way for green cyclopropane synthesis.</p>\u0000 </div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 10","pages":""},"PeriodicalIF":2.3,"publicationDate":"2026-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149084153","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
Green Organocatalysis as a Sustainable Platform for Drug Synthesis: A Perspective 绿色有机催化作为可持续的药物合成平台:展望
IF 2.3 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-09-27 DOI: 10.1002/ajoc.70551
Yashika Verma, Kamal Nayan Sharma, Seema R. Pathak
{"title":"Green Organocatalysis as a Sustainable Platform for Drug Synthesis: A Perspective","authors":"Yashika Verma,&nbsp;Kamal Nayan Sharma,&nbsp;Seema R. Pathak","doi":"10.1002/ajoc.70551","DOIUrl":"10.1002/ajoc.70551","url":null,"abstract":"<div>\u0000 \u0000 <p>Organocatalysis, which provides metal-free, effective, and highly selective transformations in line with green chemistry principles, has emerged as a sustainable method in pharmaceutical synthesis. This review highlights the fundamental concepts of organocatalysis, including catalyst types, activation modes, and environmentally safe reaction conditions like aqueous media, deep eutectic solvents, ionic liquids, mechanochemistry, and solvent-free procedures. Efficiency, scalability, and environmental performance have been further improved by combining organocatalysis with complementary green technologies like photoorganocatalysis, chemoenzymatic cascades, and recyclable catalysts. Important uses in drug synthesis are covered, with a focus on asymmetric transformations through enamine and iminium ion pathways that are related to antiviral, anticancer, and nitrogen-containing heterocyclic drugs as well as chiral building blocks. Aldol, Michael, C─N bond-forming, and cycloaddition processes are among the fundamental organocatalytic reactions that are discussed along with their application in continuous-flow systems. Overall, a strong and sustainable framework to produce next-generation drugs is presented by the convergence of green organocatalysis with advanced reaction media.</p>\u0000 </div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 9","pages":""},"PeriodicalIF":2.3,"publicationDate":"2026-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149071724","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
Lewis Acid-Catalyzed Cascade Dehydrative Annulation: Divergent Synthesis of Bi- and Tricyclic Frameworks From 2-Arylethanols and Propargylic Alcohols 路易斯酸催化级联脱水环化:由2 -芳基醇和丙炔醇发散合成双环和三环框架
IF 2.3 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-09-27 DOI: 10.1002/ajoc.70547
Yan Wang, Yunjun Wu, Yawen Li, Qingqing Liu, Jiang-Fei Li, Shaoyin Wang
{"title":"Lewis Acid-Catalyzed Cascade Dehydrative Annulation: Divergent Synthesis of Bi- and Tricyclic Frameworks From 2-Arylethanols and Propargylic Alcohols","authors":"Yan Wang,&nbsp;Yunjun Wu,&nbsp;Yawen Li,&nbsp;Qingqing Liu,&nbsp;Jiang-Fei Li,&nbsp;Shaoyin Wang","doi":"10.1002/ajoc.70547","DOIUrl":"10.1002/ajoc.70547","url":null,"abstract":"<div>\u0000 \u0000 <p>A Lewis acid-catalyzed cascade reaction to carbazole, naphthalene, tetrahydropyrano[4,3-<i>b</i>]indole, and isochromane frameworks from readily available 2-arylethan-1-ol and propargylic alcohols is described. A plausible reaction pathway is deduced from the identification and structural analysis of a key intermediate. Furthermore, the scalability of this protocol was demonstrated through a gram-scale synthesis.</p>\u0000 </div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 9","pages":""},"PeriodicalIF":2.3,"publicationDate":"2026-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149071866","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
Tf2O-Mediated One-Pot Synthesis of 3-Substituted Thiochromones via Sequential Activation of Thioesters and Carboxylic Acids 通过硫酯和羧酸的顺序活化,Tf2O介导的一锅合成3 -取代硫代色素
IF 2.3 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-09-27 DOI: 10.1002/ajoc.70543
Ghazala Khanum, Supriya Mehra, Majid Ahmad Ganie, Muneer-ul-Shafi Bhat, Bhahwal Ali Shah
{"title":"Tf2O-Mediated One-Pot Synthesis of 3-Substituted Thiochromones via Sequential Activation of Thioesters and Carboxylic Acids","authors":"Ghazala Khanum,&nbsp;Supriya Mehra,&nbsp;Majid Ahmad Ganie,&nbsp;Muneer-ul-Shafi Bhat,&nbsp;Bhahwal Ali Shah","doi":"10.1002/ajoc.70543","DOIUrl":"10.1002/ajoc.70543","url":null,"abstract":"<div>\u0000 \u0000 <p>A triflic anhydride (Tf<sub>2</sub>O)-mediated annulation of thioesters with carboxylic acids, providing a direct route to thiochromones and 3-acylthiochromones, has been reported. The transformation proceeds through a sequential activation, wherein Tf<sub>2</sub>O facilitates intramolecular Friedel–Crafts-type cyclization of the thioester to produce the thiochromone scaffold, while simultaneously activating the carboxylic acid to generate a reactive acylium intermediate, enabling regioselective electrophilic acylation at the C-3 position. This tandem cyclization–acylation sequence provides a general platform for constructing structurally diverse thiochromones.</p>\u0000 </div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 9","pages":""},"PeriodicalIF":2.3,"publicationDate":"2026-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149071864","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
Efficient Synthesis of Quinoxaline Derivatives via PIDA-Promoted Oxidative Annulation PIDA促进氧化环化高效合成喹啉衍生物
IF 2.3 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-09-27 DOI: 10.1002/ajoc.70546
Megha Kumari, Ashutosh Dey, Vikash Kumar, Rohit Kumar Maurya, Kishor Padala, Mahender Khatravath
{"title":"Efficient Synthesis of Quinoxaline Derivatives via PIDA-Promoted Oxidative Annulation","authors":"Megha Kumari,&nbsp;Ashutosh Dey,&nbsp;Vikash Kumar,&nbsp;Rohit Kumar Maurya,&nbsp;Kishor Padala,&nbsp;Mahender Khatravath","doi":"10.1002/ajoc.70546","DOIUrl":"10.1002/ajoc.70546","url":null,"abstract":"<div>\u0000 \u0000 <p>Quinoxaline derivatives represent an important class of privileged heterocyclic scaffolds widely present in natural products and biologically active molecules. Herein, we report a novel and efficient one pot, two step oxidative annulation strategy for the synthesis of quinoxalines via Phenyliodine (III) diacetate (PIDA)-mediated transformation of acetophenones/ phenyl acetylene derivatives with 1,2-diamines. This protocol utilizes inexpensive and readily available starting materials and proceeds through in situ formation of phenyl glyoxal, followed by condensation and subsequent aromatization. The method exhibits broad functional group tolerance and delivers the desired quinoxaline derivatives in high yields. Notably, PIDA serves as a transition metal-free and cost-effective oxidizing agent, highlighting the practicality and sustainability of the approach. Furthermore, this methodology enables the synthesis of biologically active compounds such as AG 1295, a PDGFR inhibitor that suppresses cell proliferation, and DPQ, a PARP inhibitor that disrupts DNA repair and induces cell death. Overall, the synthesized quinoxalines serve as valuable intermediates with promising applications in natural product synthesis and medicinal chemistry.</p>\u0000 </div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 9","pages":""},"PeriodicalIF":2.3,"publicationDate":"2026-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149071865","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
Base‐Mediated Tandem 1,6‐Conjugate Addition/Cyclization Enabling the Synthesis of 4,5‐Disubstituted 3(2H)‐Furanones From Haloacetoacetates and p‐Quinone Methides 碱基介导的串联1,6-共轭加成/环化使卤代乙酰乙酸酯和对醌类化合物合成4,5-二取代3(2H)-呋喃酮
IF 2.3 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-09-01 Epub Date: 2026-09-29 DOI: 10.1002/ajoc.70511
Vishal Karande, Amol Savekar, Nikhil Mandlik, Pratiksha Gaikwad, Suresh B. Waghmode
{"title":"Base‐Mediated Tandem 1,6‐Conjugate Addition/Cyclization Enabling the Synthesis of 4,5‐Disubstituted 3(2H)‐Furanones From Haloacetoacetates and p‐Quinone Methides","authors":"Vishal Karande,&nbsp;Amol Savekar,&nbsp;Nikhil Mandlik,&nbsp;Pratiksha Gaikwad,&nbsp;Suresh B. Waghmode","doi":"10.1002/ajoc.70511","DOIUrl":"10.1002/ajoc.70511","url":null,"abstract":"<div><div>A transition‐metal‐free tandem 1,6‐conjugate addition/cyclization of haloacetoacetates with <em>p</em>‐quinone methides has been developed as an efficient strategy for the synthesis of structurally diverse 4,5‐disubstituted 3(2H)‐furanones. The reaction proceeds under mild base‐mediated conditions, delivering the desired products in good to excellent yields (up to 94%) within short reaction times. The protocol exhibits broad substrate tolerance, accommodating electronically varied <em>p</em>‐quinone methides, polycyclic and heteroaryl systems, and isatin‐derived analogues, thereby enabling the construction of quaternary carbon centers. Notably, when isatylidene malonitriles are employed, the reaction pathway diverges to afford spiro[indoline–pyran] frameworks with high efficiency. Operational simplicity, metal‐free conditions, and scalability highlight the synthetic utility of this methodology for accessing biologically relevant oxygen‐containing heterocycles.</div></div><div>A transition‐metal‐free tandem 1,6‐conjugate addition/cyclization of haloacetoacetates with <em>p</em>‐quinone methides has been developed as an efficient strategy for the synthesis of structurally diverse 4,5‐disubstituted 3(2H)‐furanones. The reaction proceeds under mild base‐mediated conditions, delivering the desired products in good to excellent yields (up to 94%) within short reaction times. The protocol exhibits broad substrate tolerance, accommodating electronically varied <em>p</em>‐quinone methides, polycyclic and heteroaryl systems, and isatin‐derived analogues, thereby enabling the construction of quaternary carbon centers. Notably, when isatylidene malonitriles are employed, the reaction pathway diverges to afford spiro[indoline–pyran] frameworks with high efficiency. Operational simplicity, metal‐free conditions, and scalability highlight the synthetic utility of this methodology for accessing biologically relevant oxygen‐containing heterocycles.</div><div>A metal‐free, base‐catalyzed 1,6‐conjugate addition of haloacetates to <em>p‐</em>quinone methides, followed by intramolecular cyclization, enables rapid access to biologically inspired 3(2H)‐furanone derivatives in good to excellent yields (up to 94%) under mild conditions and short reaction times; isatylidene malononitriles undergo a divergent pathway to afford oxospiro[indoline–pyran] frameworks.\u0000<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (64KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 9","pages":"Article e70511"},"PeriodicalIF":2.3,"publicationDate":"2026-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148994279","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
Gold (I)‐Catalyzed (4 + 2) Annulation of 1‐(1‐Alkynyl)Cyclopropyl Ketones With 1,3,5‐Triazinanes: Synthesis of Piperidine‐Fused Furans 金(I)催化1-(1-炔基)环丙基酮与1,3,5-三嗪烷的(4 + 2)环化:哌啶熔融呋喃的合成
IF 2.3 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-09-01 Epub Date: 2026-09-29 DOI: 10.1002/ajoc.70548
Songyi Gao, Yue He, Mengnan Liu, Mengjia Zhu, Yidan Zhao, Ming Lang, Huan Jin, Shiyong Peng
{"title":"Gold (I)‐Catalyzed (4 + 2) Annulation of 1‐(1‐Alkynyl)Cyclopropyl Ketones With 1,3,5‐Triazinanes: Synthesis of Piperidine‐Fused Furans","authors":"Songyi Gao,&nbsp;Yue He,&nbsp;Mengnan Liu,&nbsp;Mengjia Zhu,&nbsp;Yidan Zhao,&nbsp;Ming Lang,&nbsp;Huan Jin,&nbsp;Shiyong Peng","doi":"10.1002/ajoc.70548","DOIUrl":"10.1002/ajoc.70548","url":null,"abstract":"<div><div>A gold(I)‐catalyzed chemoselective (4 + 2) annulation of 1‐(1‐alkynyl)cyclopropyl (ACP) ketones with 1,3,5‐triazinanes is developed, affording a series of piperidine‐fused furans in moderate‐to‐excellent yields. Chirality‐transfer experiments support an S<sub>N</sub>2‐type mechanism involving a cyclopropyloxonium‐containing vinyl‐gold intermediate (<strong>Int‐II</strong>), enabling access to enantioenriched piperidine‐fused furans. The utility of this protocol is further demonstrated by scale‐up reactions and the extension to ACP oximes for the construction of piperidine‐fused pyrroles.</div></div><div>A gold(I)‐catalyzed chemoselective (4 + 2) annulation of 1‐(1‐alkynyl)cyclopropyl (ACP) ketones with 1,3,5‐triazinanes is developed, affording a series of piperidine‐fused furans in moderate‐to‐excellent yields. Chirality‐transfer experiments support an S<sub>N</sub>2‐type mechanism involving a cyclopropyloxonium‐containing vinyl‐gold intermediate (<strong>Int‐II</strong>), enabling access to enantioenriched piperidine‐fused furans. The utility of this protocol is further demonstrated by scale‐up reactions and the extension to ACP oximes for the construction of piperidine‐fused pyrroles.</div><div>A gold(I)‐catalyzed chemoselective (4 + 2) annulation of ACP ketones with 1,3,5‐triazinanes is described, providing general and efficient access to structurally diverse piperidine‐fused furans in moderate‐to‐excellent yields under mild conditions. Scale‐up synthesis and the successful extension to ACP oximes for the construction of piperidine‐fused pyrroles highlight the synthetic potential of this protocol.\u0000<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (26KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 9","pages":"Article e70548"},"PeriodicalIF":2.3,"publicationDate":"2026-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149047939","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
4‐Chloro‐3‐nitrocoumarin as a Precursor for the Synthesis of Indolizines 4-氯-3-硝基香豆素作为吲哚嘧啶合成的前体
IF 2.3 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-09-01 Epub Date: 2026-09-29 DOI: 10.1002/ajoc.70552
Tung‐Yu Wu, Ding‐Yah Yang
{"title":"4‐Chloro‐3‐nitrocoumarin as a Precursor for the Synthesis of Indolizines","authors":"Tung‐Yu Wu,&nbsp;Ding‐Yah Yang","doi":"10.1002/ajoc.70552","DOIUrl":"10.1002/ajoc.70552","url":null,"abstract":"<div><div>A series of densely substituted indolizines were prepared via DBU‐promoted, [4+2] annulation of <em>N</em>‐acylmethyl‐1<em>H</em>‐pyrrole‐2‐carbaldehydes with 4‐chloro‐3‐nitrocoumarins in acetonitrile at room temperature. The mechanism likely involved a sequence of Michael addition/elimination, intramolecular vinylogous aldol cyclization, hydrolysis, and decarboxylative dehydration. The synthetic utility of the indolizine core was further highlighted through post‐modification transformations, including bromination, methylation, reduction, and hydrogenation reactions.</div></div><div>A series of densely substituted indolizines were prepared via DBU‐promoted, [4+2] annulation of <em>N</em>‐acylmethyl‐1<em>H</em>‐pyrrole‐2‐carbaldehydes with 4‐chloro‐3‐nitrocoumarins in acetonitrile at room temperature. The mechanism likely involved a sequence of Michael addition/elimination, intramolecular vinylogous aldol cyclization, hydrolysis, and decarboxylative dehydration. The synthetic utility of the indolizine core was further highlighted through post‐modification transformations, including bromination, methylation, reduction, and hydrogenation reactions.</div><div>A mild, DBU‐promoted [4+2] annulation of <em>N</em>‐acylmethyl‐1<em>H</em>‐pyrrole‐2‐carbaldehydes with 4‐chloro‐3‐nitrocoumarins at room temperature provides diverse indolizines. This transition‐metal‐free protocol features a multi‐step cascade mechanism and enables versatile post‐modifications.\u0000<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (12KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 9","pages":"Article e70552"},"PeriodicalIF":2.3,"publicationDate":"2026-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149047831","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
Dual Photoredox/Gold‐Catalyzed Tandem Arylation/Cyclization of 2,3‐Allenoic Acids With Aryl Diazonium Salts 用芳基重氮盐催化2,3-烯酸的双光氧化还原/金催化串联芳基化/环化
IF 2.3 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-09-01 Epub Date: 2026-09-29 DOI: 10.1002/ajoc.70545
Xingming Yan, Rongqin Zhang, Xirong Kong, Jingchao Chen, Fen Zhao, Fang Dai, Baomin Fan
{"title":"Dual Photoredox/Gold‐Catalyzed Tandem Arylation/Cyclization of 2,3‐Allenoic Acids With Aryl Diazonium Salts","authors":"Xingming Yan,&nbsp;Rongqin Zhang,&nbsp;Xirong Kong,&nbsp;Jingchao Chen,&nbsp;Fen Zhao,&nbsp;Fang Dai,&nbsp;Baomin Fan","doi":"10.1002/ajoc.70545","DOIUrl":"10.1002/ajoc.70545","url":null,"abstract":"<div><div>A tandem arylation/cyclization of 2,3‐allenoic acids with aryl diazonium salts has been achieved under visible light irradiation via a dual photoredox/gold catalytic system. This transformation provides diverse arylated butenolides in moderate to excellent yields (up to 93%) under mild conditions. The reaction tolerates diverse functional groups on both coupling partners. Mechanistic studies support a non‐chain radical pathway involving aryl radical generation. A gram‐scale reaction demonstrates the synthetic utility. This protocol provides an efficient and mild access to functionalized butenolides via dual catalysis.</div></div><div>A tandem arylation/cyclization of 2,3‐allenoic acids with aryl diazonium salts has been achieved under visible light irradiation via a dual photoredox/gold catalytic system. This transformation provides diverse arylated butenolides in moderate to excellent yields (up to 93%) under mild conditions. The reaction tolerates diverse functional groups on both coupling partners. Mechanistic studies support a non‐chain radical pathway involving aryl radical generation. A gram‐scale reaction demonstrates the synthetic utility. This protocol provides an efficient and mild access to functionalized butenolides via dual catalysis.</div><div>A mild and efficient dual photoredox/gold‐catalyzed tandem cyclization/arylation of 2,3‐allenoic acids with aryl diazonium salts is reported, providing direct access to diverse arylated butenolides in up to 93% yield under visible‐light irradiation for 10 min.\u0000<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (25KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 9","pages":"Article e70545"},"PeriodicalIF":2.3,"publicationDate":"2026-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149047879","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
Synthesis of 3,5‐Diarylated 4‐Cyano‐2‐nitrophenols via Nitro Rearrangement 硝基重排法合成3,5-二芳基化4-氰基-2-硝基苯酚
IF 2.3 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-09-01 Epub Date: 2026-09-29 DOI: 10.1002/ajoc.70540
Nagatoshi Nishiwaki, Genta Taniguchi, Taisei Yoshikawa, Kento Iwai
{"title":"Synthesis of 3,5‐Diarylated 4‐Cyano‐2‐nitrophenols via Nitro Rearrangement","authors":"Nagatoshi Nishiwaki,&nbsp;Genta Taniguchi,&nbsp;Taisei Yoshikawa,&nbsp;Kento Iwai","doi":"10.1002/ajoc.70540","DOIUrl":"10.1002/ajoc.70540","url":null,"abstract":"<div><div>3,5‐Diaryl‐4‐cyano‐4‐nitrocyclohexanones underwent bromination upon treatment with bromine and ammonium acetate. When the resulting dibromocyclohexanones were stirred in pyridine, dehydrobromination followed by nitro rearrangement occurred to furnish unsymmetrically functionalized 3,5‐diarylated 4‐cyano‐2‐nitrophenols. Computational studies suggested that the rearrangement proceeds either through a concerted pathway or via a radical‐pair intermediate.</div></div><div>3,5‐Diaryl‐4‐cyano‐4‐nitrocyclohexanones underwent bromination upon treatment with bromine and ammonium acetate. When the resulting dibromocyclohexanones were stirred in pyridine, dehydrobromination followed by nitro rearrangement occurred to furnish unsymmetrically functionalized 3,5‐diarylated 4‐cyano‐2‐nitrophenols. Computational studies suggested that the rearrangement proceeds either through a concerted pathway or via a radical‐pair intermediate.</div><div>A practical synthetic route to 3,5‐diaryl‐4‐cyano‐2‐nitrophenols, a class of unsymmetrically substituted and densely functionalized phenols, is provided. The key transformation is a nitro rearrangement of 4‐cyano‐4‐nitrocyclohexanone derivatives, which were prepared from di(benzylidene)acetones through cyano(nitro)methylation. Stepwise optimization of bromination and dehydrobromination enabled efficient conversion to the target nitrophenols.\u0000<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (13KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 9","pages":"Article e70540"},"PeriodicalIF":2.3,"publicationDate":"2026-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149048196","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
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