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Coordination-Driven Deep-Blue Fluorescence in Conjugated Bicyclic Lactams. 共轭双环内酰胺中配位驱动的深蓝色荧光。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01415
Shane MacLaren, Ryan Dean, Fatemeh Zare, Mai Huynh, Tanner George, Jason D Masuda, Sara Eisler
{"title":"Coordination-Driven Deep-Blue Fluorescence in Conjugated Bicyclic Lactams.","authors":"Shane MacLaren, Ryan Dean, Fatemeh Zare, Mai Huynh, Tanner George, Jason D Masuda, Sara Eisler","doi":"10.1021/acs.joc.6c01415","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01415","url":null,"abstract":"<p><p>Deep-blue emissions were achieved in conjugated aromatic lactams with high quantum yields in both solution and PMMA films. The optical and physical properties of isoindolinone (IIN) and boron-diaza-methene (BODAZA) fluorophores were investigated. A generalized synthetic methodology was developed for both IINs and BODAZAs and used successfully to access multiple targets. The resultant lactams were all found to be strongly emissive both in solution and in the solid state. Although the two classes of compounds are structurally related, they display significant differences in their photophysical properties as well as in their thermal and kinetic properties, which can be fine-tuned via changes to the aromatic backbone.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177876","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
Pd/Cu Synergistic Catalysis for Difluorocarbene-Mediated Synthesis of Carbamoyl-Substituted Oxindoles. 钯/铜协同催化合成氨甲酰取代的氧吲哚。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01561
Lu Wang, Yulu Du, Yanrong Zhu, Bing Zhang, Wenhui Wang, Ying Fu, Zhengyin Du
{"title":"Pd/Cu Synergistic Catalysis for Difluorocarbene-Mediated Synthesis of Carbamoyl-Substituted Oxindoles.","authors":"Lu Wang, Yulu Du, Yanrong Zhu, Bing Zhang, Wenhui Wang, Ying Fu, Zhengyin Du","doi":"10.1021/acs.joc.6c01561","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01561","url":null,"abstract":"<p><p>A palladium-catalyzed tandem Heck cyclization of N-(2-iodoaryl)acrylamides with N-methylanilines and ClCF2COONa has been developed for the synthesis of carbamoyl-substituted oxindoles bearing an all-carbon quaternary stereocenter, wherein difluorocarbene serves as the carbonyl source. This method operates under mild conditions, exhibits a broad substrate scope, and features operationally simple and safe procedures. Moreover, it expands the synthetic utility of difluorocarbene-involved domino Heck cyclizations and enables the efficient construction of diverse amide-functionalized molecular architectures containing an all-carbon quaternary center.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177998","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
Dissecting Binary and Ternary Iminoboronate Assemblies: A Calorimetric Study of Thermodynamics, Kinetics, and Allosteric Effects. 解剖二元和三元亚氨基硼酸盐组合：热力学、动力学和变构效应的量热研究。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01363
Joseba Ruiz, Eduardo Laga, Adrián Velázquez-Campoy, Jesús Del Barrio
{"title":"Dissecting Binary and Ternary Iminoboronate Assemblies: A Calorimetric Study of Thermodynamics, Kinetics, and Allosteric Effects.","authors":"Joseba Ruiz, Eduardo Laga, Adrián Velázquez-Campoy, Jesús Del Barrio","doi":"10.1021/acs.joc.6c01363","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01363","url":null,"abstract":"<p><p>Dynamic covalent assemblies derived from ortho-boronoaldehydes, including iminoboronates and boronate esters, are key structural motifs in adaptive materials, chemical sensors, and reversible bioconjugation strategies. Herein, we report a label-free assay based on isothermal titration calorimetry that provides access to observed thermodynamic and model-derived kinetic parameters associated with assembly formation under defined experimental conditions. The assay further reveals cooperative binding between amine-based nucleophiles and diols toward ortho-boronoaldehyde derivatives, providing new insight into multicomponent dynamic covalent systems.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177884","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
Why Does Bromine Sometimes Add to an Alkene and at Other Times Abstract an Allylic Hydrogen Atom? A Computational Investigation of Hydrogen Bromide Addition and Allylic Bromination. 为什么溴有时加到烯烃上，有时又抽走一个烯丙基氢原子？溴化氢加成和烯丙基溴化的计算研究。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01923
Paul R Rablen
{"title":"Why Does Bromine Sometimes Add to an Alkene and at Other Times Abstract an Allylic Hydrogen Atom? A Computational Investigation of Hydrogen Bromide Addition and Allylic Bromination.","authors":"Paul R Rablen","doi":"10.1021/acs.joc.6c01923","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01923","url":null,"abstract":"<p><p>The mechanisms of radical-mediated addition of hydrogen bromide to an alkene and of allylic bromination rely on a balance between competing addition and hydrogen abstraction by the bromine radical. In the past, addition has been postulated to be rapid and reversible, while abstraction is much slower but thermodynamically more favorable. G4 calculations are used to investigate this scenario in the case of cyclohexene. While generally supportive of the standard interpretation of the reaction, the calculations suggest that the kinetic barrier to hydrogen abstraction is often more entropic than enthalpic. A variety of other alkenes are also studied to test the limits of this framework. While the barriers to abstraction and the stability of the abstraction and addition radicals vary widely, only in the most extreme cases, such as cyclobutene, cyclopropene, and α-methylstyrene, do these variations compromise the balance between the competing reactions to an extent that interferes with effective allylic bromination. It was also observed that some bromine addition radicals are bridged in structure, especially the more highly substituted ones, while chlorine addition radicals are only rarely bridged.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177991","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
Electrolyte- and Catalyst-Free Electrochemical Synthesis of Unsymmetrical Diorganoyl Selenides. 非对称硒二有机酰基的无电解质和无催化剂电化学合成。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c02068
Linheng He, Yufen Lv, Qingxia Luo, Minhang Zhou, Yuyu Tan, Wenbo Zhang, Wei Wei
{"title":"Electrolyte- and Catalyst-Free Electrochemical Synthesis of Unsymmetrical Diorganoyl Selenides.","authors":"Linheng He, Yufen Lv, Qingxia Luo, Minhang Zhou, Yuyu Tan, Wenbo Zhang, Wei Wei","doi":"10.1021/acs.joc.6c02068","DOIUrl":"https://doi.org/10.1021/acs.joc.6c02068","url":null,"abstract":"<p><p>A facile electrocatalytic radical coupling of Katritzky salts with diselenides for the efficient synthesis of various alkyl aryl unsymmetrical selenides has been developed under mild conditions. This sustainable protocol is driven by renewable electrical energy, features a broad substrate scope, good functional group tolerance, and practical scalability. The reaction proceeds without the need for any external electrolyte, catalyst, or metal, in accordance with green chemistry principles.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177833","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
FeBr3-Catalyzed Aromatization-C-O Bond Cleavage Process for Construction of Aryl-Substituted Prostaglandin Skeleton. 二氧化催化芳构化- c - o键裂解构建芳基取代前列腺素骨架的过程。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c02150
Nai-Xuan Liu, Jian-Ting Sun, Rui-Jun Ma, Yu-Ying Zhang, Jing-Bo Zhou, Jian-Liang Ye, Bang-Guo Wei
{"title":"FeBr3-Catalyzed Aromatization-C-O Bond Cleavage Process for Construction of Aryl-Substituted Prostaglandin Skeleton.","authors":"Nai-Xuan Liu, Jian-Ting Sun, Rui-Jun Ma, Yu-Ying Zhang, Jing-Bo Zhou, Jian-Liang Ye, Bang-Guo Wei","doi":"10.1021/acs.joc.6c02150","DOIUrl":"https://doi.org/10.1021/acs.joc.6c02150","url":null,"abstract":"<p><p>Prostaglandins exhibit therapeutic potential in multiple diseases and the incorporation of aromatic rings into their side chains can often enhance their corresponding biological activities. Although more than 20 kinds of drugs are currently used in clinical practice, there are huge difficulties in the preparation of both active pharmaceutical ingredients and preparations. Prostaglandins directly substituted by aryl groups may overcome these difficulties; however, their preparation remains challenging, and only a few synthetic methods have been reported to date. Herein, we describe a novel FeBr3/ligand-catalyzed aromatization-C-O bond cleavage process that provides access to aryl-substituted prostaglandin skeletons.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177854","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
Carbene-Catalyzed Enantioselective Formal [4 + 2] Reaction for Rapid Synthesis of 1-Azaspiro[4,5]decane Derivatives. 羰基催化对映选择性正[4 + 2]反应快速合成1-氮杂螺[4,5]十烷衍生物
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01282
Jun Sun, Yong-Gui Liu, Shi-Chun Jiang, Guan-Xin Hu, Deng-Yue Liu, Jing-Song Lv, Xiao-Qun Yang, Ying-Guo Liu
{"title":"Carbene-Catalyzed Enantioselective Formal [4 + 2] Reaction for Rapid Synthesis of 1-Azaspiro[4,5]decane Derivatives.","authors":"Jun Sun, Yong-Gui Liu, Shi-Chun Jiang, Guan-Xin Hu, Deng-Yue Liu, Jing-Song Lv, Xiao-Qun Yang, Ying-Guo Liu","doi":"10.1021/acs.joc.6c01282","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01282","url":null,"abstract":"<p><p>An NHC-promoted formal [4 + 2] cycloaddition reaction is developed for quick access to chiral 1-aza-spirocyclohexane pyrrolidone molecules bearing quaternary chiral carbon centers. A broad scope of β-methylenals and 5-ene pyrrolin-4-one substrates worked well in this reaction. A diversity of chiral 1-aza-spirocyclohexane pyrrolidone molecules can be afforded in generally moderate to good yields and excellent enantioselectivities. The chiral products obtained from this protocol can be transformed into multifunctional chiral spirocyclohexane pyrrolidone derivatives through simple operations.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177899","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
Practical C(sp3)-F Bond Construction via Metal-Free Heterogeneous Photodecarboxylative Fluorination in Continuous Flow. 连续流无金属非均相光脱羧氟化构建C(sp3)-F键
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01769
Caiwen Wan, Ruolan Leng, Yingjie Zhu, Changtong Shao, Junwen Shu, Zhangyi Ran, Yexuan Luo, Jie Gao, Dingfeng Yang, Yuanyuan Li
{"title":"Practical C(sp3)-F Bond Construction via Metal-Free Heterogeneous Photodecarboxylative Fluorination in Continuous Flow.","authors":"Caiwen Wan, Ruolan Leng, Yingjie Zhu, Changtong Shao, Junwen Shu, Zhangyi Ran, Yexuan Luo, Jie Gao, Dingfeng Yang, Yuanyuan Li","doi":"10.1021/acs.joc.6c01769","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01769","url":null,"abstract":"<p><p>We report a robust, metal-free heterogeneous photocatalytic protocol for the direct decarboxylative fluorination of aliphatic carboxylic acids utilizing graphitic carbon nitride (g-C3N4). Operating under visible light, this strategy exhibits good substrate generality, particularly for activated aliphatic carboxylic acids and facilitates the late-stage functionalization of complex pharmaceutical scaffolds. The operationally simple photocatalyst can be recycled over seven consecutive cycles while maintaining high catalytic efficacy. Crucially, a continuous-flow, gram-scale synthesis validates its practical scalability. Mechanistic studies confirm a closed-loop photoredox pathway, establishing a versatile platform for C(sp3)-F bond construction.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177993","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
Highly Diastereoselective Synthesis of Trifluoromethylated Spirocyclopropanes from 2-(2'-Ketoalkyl)-1,3-Indandiones and CF3-Imidoyl Sulfoxonium Ylides. 由2-（2′-酮烷基）-1,3-茚二酮和cf3 -咪酰基亚砜酰体高度非对映选择性合成三氟甲基化螺环丙烷。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01506
Biral Kanti Pal, Susmita Sahoo, Barla Thirupathi
{"title":"Highly Diastereoselective Synthesis of Trifluoromethylated Spirocyclopropanes from 2-(2'-Ketoalkyl)-1,3-Indandiones and CF3-Imidoyl Sulfoxonium Ylides.","authors":"Biral Kanti Pal, Susmita Sahoo, Barla Thirupathi","doi":"10.1021/acs.joc.6c01506","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01506","url":null,"abstract":"<p><p>A metal-free and highly diastereoselective strategy for the synthesis of trifluoromethylated spirocyclopropanes has been developed using CF3-imidoyl sulfoxonium ylides (TFISYs) and 2-(2'-ketoalkyl)-1,3-indandiones. The transformation proceeds through a base-mediated cascade process to furnish densely functionalized trifluoromethylated spirocyclopropanes in good to excellent yields with excellent diastereoselectivity. The protocol exhibits a broad substrate scope, gram-scale applicability, and synthetic versatility through post-functionalization, providing efficient access to fluorinated spirocyclic architectures of potential medicinal relevance.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177847","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
Chemoselective Electrochemical Synthesis of 3-Hydroxyisoindolinones from Phthalimide Imines. 邻苯二胺亚胺化学选择性电化学合成3-羟基异吲哚酮。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01017
Xi Zhang, Yicai Li, Qiaohong Xu, Zenghui Ye, Wei-Yuan Ma, Jian-Xing Xu, Fengzhi Zhang
{"title":"Chemoselective Electrochemical Synthesis of 3-Hydroxyisoindolinones from Phthalimide Imines.","authors":"Xi Zhang, Yicai Li, Qiaohong Xu, Zenghui Ye, Wei-Yuan Ma, Jian-Xing Xu, Fengzhi Zhang","doi":"10.1021/acs.joc.6c01017","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01017","url":null,"abstract":"<p><p>We report an electrochemical method for the radical-radical coupling of alkyl iodides with phthalimide imines under mild conditions. This operationally simple electro-reductive procedure enables selective reduction of carbonyl groups, offering an efficient route to access functionalized 3-hydroxyisoindolinones in moderate-to-excellent yields. Notably, the highly functionalized 3-hydroxyisoindolinones have shown promising bioactivity in preliminary assessments, pointing to the significant potential of this chemical scaffold for anticancer cell applications. A comparative analysis has demonstrated that the hydrazone moiety within the product structure plays an indispensable role in conferring bioactivity.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177881","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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