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Unexpected T3P-Mediated Enaminoester Cascade Cyclization to Access 4-Pyridones. 意想不到的t3p介导的漆胺酯级联环化以获得4-吡啶酮。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-16 DOI: 10.1021/acs.joc.6c01549
Manubolu Guravaiah, Thondooru Sruthi, R Menaka, Vinod D Jadhav, Bandi Ramakrishna, Siddaiah Vidavalur, Katta Venkateswarlu
{"title":"Unexpected T3P-Mediated Enaminoester Cascade Cyclization to Access 4-Pyridones.","authors":"Manubolu Guravaiah, Thondooru Sruthi, R Menaka, Vinod D Jadhav, Bandi Ramakrishna, Siddaiah Vidavalur, Katta Venkateswarlu","doi":"10.1021/acs.joc.6c01549","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01549","url":null,"abstract":"<p><p>The development of novel one-pot cascade protocols for synthesizing biologically significant nitrogen heterocycles plays a vital role in drug discovery and development. We report here a new and unexpected T3P-mediated one-pot transformation of amines and β-ketoesters into 4-pyridones via an enaminoester cascade cyclization process. This method affords structurally diverse and readily multi-tailorable 4-pyridones with up to 99% yields in 1 h at 70 °C, providing rapid access to a pharmaceutically significant heterocyclic motif. Furthermore, this method shows a low E-factor (5.18), a low process mass intensity (PMI, 6.18), and an excellent GreenScore (86). To the best of our knowledge, this study presents the first highly efficient and straightforward multicomponent synthesis of 4-pyridones using readily available substrates.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149190240","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Resonance-Structure Collapse Enables Aromaticity-Controlled Design of Small Singlet-Fission Chromophore Candidates 共振结构坍缩使得芳香控制设计小型单重裂变生色团候选体成为可能
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-16 Epub Date: 2026-10-02 DOI: 10.1021/acs.joc.6c01083
Luis Leyva-Parra, Ricardo Pino-Rios
{"title":"Resonance-Structure Collapse Enables Aromaticity-Controlled Design of Small Singlet-Fission Chromophore Candidates","authors":"Luis Leyva-Parra,&nbsp;Ricardo Pino-Rios","doi":"10.1021/acs.joc.6c01083","DOIUrl":"10.1021/acs.joc.6c01083","url":null,"abstract":"<p>Precise control of singlet and tripletexcited-stateenergies isessential for identifying singlet-fission chromophore candidates,particularly in compact heteroarenes with competing resonance structures.Here, we show that heteroatom-controlled resonance-structure selectionprovides a chemically transparent strategy for tuning excited-stateenergetics. Comparison of normal-type and iso-type benzannulated five-memberedheteroarenes across the NH, O, S, Se, and Te series reveals that heteroatomconnectivity governs the redistribution of π-electron delocalizationupon excitation. Iso-type connectivity consistently stabilizes <em>T</em><sub>1</sub> and increases <em>E</em>(<em>S</em><sub>1</sub>)/<em>E</em>(<em>T</em><sub>1</sub>),a trend reproduced by vertical TD-DFT, the Zeng–Hoffmann–Ananthscheme, fully adiabatic calculations, and DLPNO-STEOM-CCSD. Calculationson the experimentally established singlet-fission chromophore 1,3-diphenylisobenzofuranfurther support these protocols as comparative screening tools. Aromaticityand spin-density analyses show that <em>T</em><sub>1</sub> stabilization arises from topology-controlled aromaticity partitioning,whereby the six-membered ring retains local Hückel-like aromaticcharacter while the unpaired electrons are preferentially localizedon the adjacent five-membered ring. Chalcogen substitution and functionalizationpreserve this mechanism, with selected substituted iso-type derivativessatisfying the fully adiabatic 2<em>E</em>(<em>T</em><sub>1</sub>) &lt; <em>E</em>(<em>S</em><sub>1</sub>) criterion. These results establish resonance-structure controlas an electronic-structure principle for identifying compact, tunablesinglet-fission chromophore candidates.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"91 41","pages":"13584–13594"},"PeriodicalIF":3.3,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088573","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
One-Pot Synthesis of 1-Pyrrolines via Rh2(esp)2-Catalyzed Intermolecular Reaction of Allylic Azides with Diazomalonates Followed by DBU-Mediated Allylic Imine Cyclization Rh2（特别是）2催化烯丙基叠氮化物与重氮膦酸酯的分子间反应及dbu介导的烯丙基亚胺环化一锅合成1-吡咯啉
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-16 Epub Date: 2026-09-29 DOI: 10.1021/acs.joc.6c00301
Yi-Fan Wang, Rui Li, Yang Ji, Peiming Gu
{"title":"One-Pot Synthesis of 1-Pyrrolines via Rh2(esp)2-Catalyzed Intermolecular Reaction of Allylic Azides with Diazomalonates Followed by DBU-Mediated Allylic Imine Cyclization","authors":"Yi-Fan Wang,&nbsp;Rui Li,&nbsp;Yang Ji,&nbsp;Peiming Gu","doi":"10.1021/acs.joc.6c00301","DOIUrl":"https://doi.org/10.1021/acs.joc.6c00301","url":null,"abstract":"<p>A one-pot reaction for the synthesisof 1-pyrrolinesfrom allylicazides and diazomalonates has been designed and developed. This conversioninvolves a sequential two-step process of interception of a diazomalonateby the allylic azide and base-mediated cyclization of the resultant <em>N</em>-allyl imine intermediate. Rh<sub>2</sub>(esp)<sub>2</sub> was identified as the optimized catalyst for the initial carbenoidinterception step, while DBU proved to be an effective promoter forthe cyclization step, efficiently affording 30 diverse 1-pyrrolinesin up to 91% yield under very mild conditions.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"91 41","pages":"13777–13783"},"PeriodicalIF":3.3,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149174002","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Revival of Thermal Aziridine–Alkene Cycloaddition: Pyrrolidine Synthesis in Terpenoid-Based Deep Eutectic Solvents 热氮吡啶-烯烃环加成的复兴：在萜类深共晶溶剂中合成吡咯烷
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-16 Epub Date: 2026-10-02 DOI: 10.1021/acs.joc.6c01138
Lalita Radtanajiravong, Nattawadee Nimsawang
{"title":"Revival of Thermal Aziridine–Alkene Cycloaddition: Pyrrolidine Synthesis in Terpenoid-Based Deep Eutectic Solvents","authors":"Lalita Radtanajiravong,&nbsp;Nattawadee Nimsawang","doi":"10.1021/acs.joc.6c01138","DOIUrl":"10.1021/acs.joc.6c01138","url":null,"abstract":"<p>A synthesis of pyrrolidines <em>via</em> atom-economicaziridine–alkene cycloaddition mediated by hydrophobic deepeutectic solvents (HDESs) is reported. HDESs, prepared from naturallyoccurring terpenoid compounds, serve as high-boiling reaction mediaand as alternatives to conventional petroleum-based solvents. Thisprotocol proceeds in the presence of air without any special precautions,offering an approach to highly substituted pyrrolidine scaffolds.A broad range of <em>N</em>-aryl aziridines is used as azomethineylide precursors, delivering pyrrolidines in up to 94% isolated yield.The methodology is further extended to a one-pot double cycloadditiondirectly from azide starting material, with solvent reusability andgram-scale synthesis also demonstrated.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"91 41","pages":"13788–13792"},"PeriodicalIF":3.3,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088574","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Discovery and Total Synthesis of Seco-acorane Sesquiterpenoids from Chloranthus holostegius: Determination of Absolute Configuration and Spontaneous Acetalization 从绿耳草中发现并合成了二松果烷倍半萜类化合物：绝对构型和自发缩醛反应的测定
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-16 Epub Date: 2026-10-01 DOI: 10.1021/acs.joc.6c01558
Shihao Cheng, Jie Wen, Houli Jiang, Yuhang Zhou, Yi Zhu, Danyang Zhang, Lingyi Kong, Jun Luo
{"title":"Discovery and Total Synthesis of Seco-acorane Sesquiterpenoids from Chloranthus holostegius: Determination of Absolute Configuration and Spontaneous Acetalization","authors":"Shihao Cheng,&nbsp;Jie Wen,&nbsp;Houli Jiang,&nbsp;Yuhang Zhou,&nbsp;Yi Zhu,&nbsp;Danyang Zhang,&nbsp;Lingyi Kong,&nbsp;Jun Luo","doi":"10.1021/acs.joc.6c01558","DOIUrl":"10.1021/acs.joc.6c01558","url":null,"abstract":"<p>Shimianoids A–C, rare nor-acorane sesquiterpenoid(<strong>1</strong>) and aromatic <em>seco</em>-acoranes (<strong>2</strong>/<strong>3</strong>) featuring an aldehyde group, along withtheir spontaneousacetalization products with methanol-<em>d</em><sub>4</sub> (<strong>2a</strong>/<strong>3a</strong>), were isolated and elucidatedfrom <em>Chloranthus holostegius</em> var. <em>shimianensis</em>. The undetermined absolute configurationsof the flexible side chain and intriguing spontaneous acetalizationof compounds <strong>2</strong>/<strong>3</strong> prompted our total synthesisstudy. Ultimately, compounds <strong>2</strong>/<strong>3</strong> and theiracetalization products with methanol-<em>d</em><sub>4</sub> (<strong>2a</strong>/<strong>3a</strong>) and CH<sub>3</sub>OH (<strong>2b</strong>/<strong>3b</strong>) were synthesized via a redox-relay Heck reactionof 4-tolylboronic acid with (±)-sulcatol, followed by oxidationand acetalization. The absolute configurations of C7/10 at the flexibleside chain were determined by Mosher’s and ECD methods of thesynthetic intermediate, and the spontaneous reversible acetalizationwas confirmed. Finally, a library of 26 aromatic <em>seco</em>-acorane sesquiterpenoids was constructed for bioactivity screening.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"91 41","pages":"13667–13673"},"PeriodicalIF":3.3,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149092227","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Chemodivergent Synthesis of Indole Derivatives: [2 + 3]-Annulation of Oxindole-Derived MBH Carbonates with α-Enolic Dithioesters and Subsequent Branching Transformations 吲哚衍生物的化学发散合成：[2+ 3]-吲哚衍生物与α-烯烯二硫酯的环化及其分支转化
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-16 Epub Date: 2026-09-30 DOI: 10.1021/acs.joc.6c01172
Yun Luo, Sifeng Li, Peng Li, Bin Cheng, Yixuan He, Si Zhao, Ying Zhang, Ping Wu, Taimin Wang, Peijun Liu
{"title":"Chemodivergent Synthesis of Indole Derivatives: [2 + 3]-Annulation of Oxindole-Derived MBH Carbonates with α-Enolic Dithioesters and Subsequent Branching Transformations","authors":"Yun Luo,&nbsp;Sifeng Li,&nbsp;Peng Li,&nbsp;Bin Cheng,&nbsp;Yixuan He,&nbsp;Si Zhao,&nbsp;Ying Zhang,&nbsp;Ping Wu,&nbsp;Taimin Wang,&nbsp;Peijun Liu","doi":"10.1021/acs.joc.6c01172","DOIUrl":"10.1021/acs.joc.6c01172","url":null,"abstract":"<p>A chemodivergent synthetic strategy for constructinga series ofstructurally diverse indole derivatives has been developed, utilizingoxindole-derived Morita-Baylis-Hillman (MBH) carbonates and α-enolicdithioesters as key building blocks. By leveraging the unique reactivityof both components, including the multisite reactivity of α-enolicdithioesters and the versatile reaction potential of oxindole-basedMBH derivatives, the reaction proceeds via an initial [2 + 3] annulationto afford polysubstituted thiophene scaffolds tethered with an oxindolemotif. This common annulation intermediate undergoes branching transformationsunder tailored reaction conditions: lactam-enolization-mediated trappingdelivers hydrothiophene-tethered indoles, whereas base-promoted skeletalrearrangement furnishes two classes of spirooxindole derivatives spirofusedwith cyclopentadienes or thiopyrans.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"91 41","pages":"13609–13621"},"PeriodicalIF":3.3,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088152","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Transition-Metal-Free Regioselective Construction of Cyano- and Phosphonyl Tetrazole Derivatives 无过渡金属的氰基和膦基四唑衍生物的区域选择性构造
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-16 Epub Date: 2026-09-30 DOI: 10.1021/acs.joc.6c01824
Yufeng Wang, Zeya Xu, Ruiqi Liu, Yuting Zheng, Jia Zhou, Xiaoran Chen, Tingpu Guo, Yulei Zhao
{"title":"Transition-Metal-Free Regioselective Construction of Cyano- and Phosphonyl Tetrazole Derivatives","authors":"Yufeng Wang,&nbsp;Zeya Xu,&nbsp;Ruiqi Liu,&nbsp;Yuting Zheng,&nbsp;Jia Zhou,&nbsp;Xiaoran Chen,&nbsp;Tingpu Guo,&nbsp;Yulei Zhao","doi":"10.1021/acs.joc.6c01824","DOIUrl":"10.1021/acs.joc.6c01824","url":null,"abstract":"<p>A Brønsted base-promoted, transition-metal-free[3 + 2] cycloadditionfor the regioselective synthesis of cyano- and phosphonyl-substitutedtetrazoles is reported. Compared to readily decomposing diazoniumsalts, the use of arylazo sulfones not only enhances safety but alsoavoids the need for precious metal catalysts. Arylazo sulfones exhibitexcellent reactivity, whereas other commonly used azo compounds arenearly ineffective. Modification of natural products, synthesis ofdual tetrazoles, gram-scale reactions, and investigations into producttransformation further highlight the promising applications.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"91 41","pages":"13743–13748"},"PeriodicalIF":3.3,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088167","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Rh(III)-Catalyzed Direct C7 Alkylation of Indolines with Nitroalkenes Rh（III）催化吲哚与硝基烯的C7直接烷基化反应
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-16 Epub Date: 2026-09-29 DOI: 10.1021/acs.joc.6c01873
Shuang-Liang Liu, Jiejie Wang, Lin Liu, Kaixin Cheng, Hao-Ran Yang, Liming Zhou
{"title":"Rh(III)-Catalyzed Direct C7 Alkylation of Indolines with Nitroalkenes","authors":"Shuang-Liang Liu,&nbsp;Jiejie Wang,&nbsp;Lin Liu,&nbsp;Kaixin Cheng,&nbsp;Hao-Ran Yang,&nbsp;Liming Zhou","doi":"10.1021/acs.joc.6c01873","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01873","url":null,"abstract":"<p>The Rh(III)-catalyzed C7-alkylation of indolines withnitroalkenesunder an ambient atmosphere is disclosed, affording diverse 7-(2-nitroalkyl)indolineswith excellent chemo- and regioselectivity. The directing group isreadily removable, and the resulting products can be oxidized to deliver7-(2-nitroalkyl)indoles. Moreover, a plausible mechanism is proposedon the basis of control experiments.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"91 41","pages":"13812–13817"},"PeriodicalIF":3.3,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149173831","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Sequential Dual Catalysis Merging Enantioselective Cu-Catalyzed Conjugate Addition with Intramolecular Pd/Ir-Catalyzed Allylic Alkylation. 顺序双催化合并对映选择性cu催化共轭加成和分子内Pd/ ir催化烯丙基烷基化。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-16 DOI: 10.1021/acs.joc.6c02121
Sebastian Strähler, Anthony Kromodimedjo, Rens Clijnk, Ümeyr Tasova, Remco Broersen, H Daniël Preschel, Olivier Riant, Eelco Ruijter
{"title":"Sequential Dual Catalysis Merging Enantioselective Cu-Catalyzed Conjugate Addition with Intramolecular Pd/Ir-Catalyzed Allylic Alkylation.","authors":"Sebastian Strähler, Anthony Kromodimedjo, Rens Clijnk, Ümeyr Tasova, Remco Broersen, H Daniël Preschel, Olivier Riant, Eelco Ruijter","doi":"10.1021/acs.joc.6c02121","DOIUrl":"https://doi.org/10.1021/acs.joc.6c02121","url":null,"abstract":"<p><p>The combination of asymmetric conjugate addition and allylic alkylation has emerged as a powerful strategy for the stereocontrolled construction of complex molecules. However, such transformations have been largely limited to intermolecular processes and have not been explored on β-substituted enones. Herein, we report a sequential one-pot dual catalytic approach that merges Cu-catalyzed enantioselective conjugate addition of trialkylaluminum reagents with intramolecular Pd- or Ir-catalyzed allylic alkylation. The methodology enables the synthesis of fused and bridged bicyclic frameworks bearing all-carbon quaternary stereocenters in good yields and high enantioselectivities. In addition, catalyst-controlled stereodivergent synthesis was achieved through the combination of enantiomeric Cu and Ir catalysts, providing selective access to all four stereoisomers of a representative bicyclic product. This work provides a versatile strategy for the synthesis of enantioenriched bicyclic architectures, and its synthetic utility was further demonstrated through a gram-scale synthesis and application to the formal syntheses of (+)-β-gorgonene and (+)-8,9-epi-β-gorgonene.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149190208","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Selectfluor-Mediated Cascade Lactonization-Selenylation of N-Alkynyl Carbamates. 选择氟介导的级联内酯化- n-炔基氨基甲酸酯的硒化。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-16 DOI: 10.1021/acs.joc.6c01860
Yuting Feng, Lele Ouyang, Wanzhu Chen, Wanrou Xiong, Honggui Huang, Yaqian Li, Jinhui Cai
{"title":"Selectfluor-Mediated Cascade Lactonization-Selenylation of N-Alkynyl Carbamates.","authors":"Yuting Feng, Lele Ouyang, Wanzhu Chen, Wanrou Xiong, Honggui Huang, Yaqian Li, Jinhui Cai","doi":"10.1021/acs.joc.6c01860","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01860","url":null,"abstract":"<p><p>Herein, we have devised a metal-free strategy that enables the efficient synthesis of various 4-selenylated oxazolones via a Selectfluor-mediated cascade lactonization/selenylation of N-alkynyl carbamates. This protocol forges a C-Se bond and a C-O bond while constructing one ring in a single step. The key to success relies on the in situ generation of an electrophilic RSeF species from Selectfluor and diselenides. This method stands out for its extensive substrate scope, high compatibility across diverse functional groups, scalable reaction, and valuable transformations. Mechanistic experiments indicate that a cationic pathway, rather than a radical pathway, is likely involved.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149190255","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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