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Stereoselective Synthesis of cis-1,3-Diaminocyclitols via a Tandem Iodocyclization/Ring-Opening Strategy. 通过串联碘环化/开环策略立体选择性合成顺-1,3-二氨基环醇。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c02002
Guanghai Cheng, Shuo Du, Chengshan Yuan, Xiaolei Wang
{"title":"Stereoselective Synthesis of cis-1,3-Diaminocyclitols via a Tandem Iodocyclization/Ring-Opening Strategy.","authors":"Guanghai Cheng, Shuo Du, Chengshan Yuan, Xiaolei Wang","doi":"10.1021/acs.joc.6c02002","DOIUrl":"https://doi.org/10.1021/acs.joc.6c02002","url":null,"abstract":"<p><p>Aminoglycoside antibiotics containing the 1,3-diaminocyclohexanetriol core, namely, 2-deoxystreptamine (2-DOS), represent a class of clinically widely used anti-infective agents with significant research importance. However, the current lack of synthetic strategies for constructing diverse aminocyclitol cores has restricted access to privileged structures within this class of antibiotics. Herein, we have successfully developed a concise and practical method for constructing the cis-1,3-diaminocyclitol core framework. Initially, readily available amide-substituted cycloalkenyl carbamate derivatives undergo a tandem reaction mediated by N-iodosuccinimide (NIS) to furnish fused-ring products bearing two heterocyclic rings and featuring a cis-1,3-diamine framework. This reaction employs two native nitrogen functionalities as endogenous nucleophiles, enabling a rapid increase in molecular complexity. Notably, two heterocyclic rings in the fused-ring compounds can undergo base-promoted ring-opening to afford cis-1,3-diaminocyclitols, demonstrating the practical synthetic utility of this transformation.</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":"149190273","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
Synthesis and Properties of Phenanthrene-Containing Expanded Porphyrin-Based BODIPY Derivatives. 含菲扩展卟啉BODIPY衍生物的合成与性能研究。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01131
Hao Chen, Cun Yang, Shuo Wang, Dasheng Geng, Yaowen Liu, Haiyu Ma, Jingna Li, Wenjie Lu, Baichuan Liu, Zongqi Zhang
{"title":"Synthesis and Properties of Phenanthrene-Containing Expanded Porphyrin-Based BODIPY Derivatives.","authors":"Hao Chen, Cun Yang, Shuo Wang, Dasheng Geng, Yaowen Liu, Haiyu Ma, Jingna Li, Wenjie Lu, Baichuan Liu, Zongqi Zhang","doi":"10.1021/acs.joc.6c01131","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01131","url":null,"abstract":"<p><p>Two phenanthrene-containing expanded porphyrins were synthesized by acid-catalyzed condensation and subsequently complexed with boron trifluoride etherate to afford BODIPY derivatives. Their structures and properties were investigated by spectroscopic, crystallographic, and computational methods. Changing the meso-substituent from 3,5-di-tert-butylphenyl (1) to 2,4,6-trimethylphenyl (2) significantly affects their photophysical properties. Notably, 2 exhibits large Stokes shifts (3471-3739 cm-1) and moderate fluorescence quantum yields (31-44%) in different organic solvents.</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":"149177967","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
Stereoselective Defluorinative Thiolation of gem-Difluoroalkenes with Thiols via Nucleophilic Substitution. 通过亲核取代对宝石-二氟烯烃与硫醇的立体选择性脱氟硫代化。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01159
Xin Guo, Dandan Xia, Huanyi Guo, Pan-Pan Zhou, Jia Jia
{"title":"Stereoselective Defluorinative Thiolation of gem-Difluoroalkenes with Thiols via Nucleophilic Substitution.","authors":"Xin Guo, Dandan Xia, Huanyi Guo, Pan-Pan Zhou, Jia Jia","doi":"10.1021/acs.joc.6c01159","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01159","url":null,"abstract":"<p><p>Monofluoroalkenes are valuable mimics of enol and amide bonds, making them important structural motifs in drug discovery. Herein, we report a transition-metal-free, stereoselective defluorinative thiolation of gem-difluoroalkenes with thiols under simple base promotion. This transformation proceeds efficiently through a nucleophilic substitution pathway, affording a broad array of monofluoroalkenyl sulfides in generally good yields with excellent stereoselectivities (Z/E up to 24:1). This protocol features a broad substrate scope and excellent functional group tolerance, representing a convenient approach to stereodefined monofluoroalkenyl sulfides.</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":"149178004","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
Synthesis of Succinic Acids via Electrochemical Dicarboxylation of Aryl Terminal Alkynes with CO2. 芳基末端炔与CO2电化学二羧基化合成琥珀酸的研究。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01552
Qianqian Wei, Shuping Zhu, Manxin Sun, Yanhua Zhang
{"title":"Synthesis of Succinic Acids via Electrochemical Dicarboxylation of Aryl Terminal Alkynes with CO2.","authors":"Qianqian Wei, Shuping Zhu, Manxin Sun, Yanhua Zhang","doi":"10.1021/acs.joc.6c01552","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01552","url":null,"abstract":"<p><p>An environment-friendly and efficient method for the synthesis of succinic acids has been developed through the electrochemical dicarboxylation of aryl terminal alkynes with CO2. The reaction proceeds smoothly at a certain constant current in acetonitrile with manganese(II) carbonate (MnCO3) as the additive, giving the desired succinic acids with up to 85% isolated yield. The system is applicable to various aryl terminal alkynes, exhibiting good functional group tolerance. This method may open up a window for the application of the electrochemical strategy in the synthesis of multicarboxylic acids.</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":"149177953","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
Synthesis of Indole-Fused Oxepane through (4 + 3) Cycloadditions of Indolyldimethanols with Pyrazolones. 吲哚基二甲醇与吡唑酮（4 + 3）环加成合成吲哚-氧杂烷。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01650
Pingde Tao, Shi-Wu Li
{"title":"Synthesis of Indole-Fused Oxepane through (4 + 3) Cycloadditions of Indolyldimethanols with Pyrazolones.","authors":"Pingde Tao, Shi-Wu Li","doi":"10.1021/acs.joc.6c01650","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01650","url":null,"abstract":"<p><p>An efficient phosphoric acid-catalyzed cycloaddition reaction between pyrazolones and 2-indolyldimethanols for the construction of indole-fused seven-membered oxepane skeletons was developed. This protocol featured excellent functional group tolerance, broad substrate generality, and high reaction yields. Moreover, the scalable gram-scale synthesis and facile product derivatization further demonstrated its synthetic practicability. This work provided a reliable strategy for the assembly of complex oxepane heterocyclic frameworks.</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":"149190218","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(II)-Catalyzed Decarboxylative ortho-Amidation of Benzyl Thiocyanates with Oxamic Acids Unveiling -SCN as a Bidentate Directing Group. Pd(II)-催化苯硫氰酸酯与肟酸脱羧邻酰胺化，揭示-SCN作为双齿导向基团。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01481
Sandeep Singh, Prachi Rai, Santanab Giri, Rakesh K Mishra, Saroj Ranjan De
{"title":"Pd(II)-Catalyzed Decarboxylative ortho-Amidation of Benzyl Thiocyanates with Oxamic Acids Unveiling -SCN as a Bidentate Directing Group.","authors":"Sandeep Singh, Prachi Rai, Santanab Giri, Rakesh K Mishra, Saroj Ranjan De","doi":"10.1021/acs.joc.6c01481","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01481","url":null,"abstract":"<p><p>A Pd(II)-catalyzed highly regiospecific ortho-amidation of benzyl thiocyanates with N,N-disubstituted oxamic acids has been developed using AgOAc as an oxidant. Thiocyanate (-SCN) has been introduced as a multicoordinating weak-directing group in C-H activation. The decarboxylative coupling proceeds under operationally simple conditions with a broad substrate scope and excellent functional group tolerance. A variety of substituted, secondary, and heterocyclic benzyl thiocyanates efficiently undergo ortho-amidation with diverse oxamic acids to afford a series of ortho-amidation products in moderate to excellent yields. Density functional theory (DFT) calculations established that the thiocyanate (-SCN) moiety acts as a bidentate directing group, coordinating to palladium through both nitrogen and sulfur atoms sequentially, thereby leading to the formation of an unusual monomeric Pd(III)-intermediate. This Pd(III)-intermediate preferentially undergoes reductive elimination to generate a Pd(I)-species rather than participating in single-electron oxidation or disproportionation pathways. The Pd(II)-catalyst is regenerated from Pd(I) using silver(I) as an oxidant. The established protocol offers an efficient and atom-economical route for C-H amidation, expanding the versatility of Pd-catalyzed C-H functionalization strategies.</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":"149177895","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
Defluorinative Annulation Triggered by Lewis Base-Promoted O-Alkenylation/[3,3]-Sigmatropic Rearrangement of Fluoro-N-arylhydroxylamines: Synthesis of Fused-Indoline Derivatives. 路易斯碱促进的o-烯基化/[3,3]-氟- n -芳基羟胺的异位重排引发的去氟环化：融合吲哚衍生物的合成。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01446
Lei Yang, Dan-Dan Wan, Meng-Yu Liu, Zhong-Lin Wei, Wei-Wei Liao
{"title":"Defluorinative Annulation Triggered by Lewis Base-Promoted O-Alkenylation/[3,3]-Sigmatropic Rearrangement of Fluoro-N-arylhydroxylamines: Synthesis of Fused-Indoline Derivatives.","authors":"Lei Yang, Dan-Dan Wan, Meng-Yu Liu, Zhong-Lin Wei, Wei-Wei Liao","doi":"10.1021/acs.joc.6c01446","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01446","url":null,"abstract":"<p><p>A Lewis base-promoted defluorinative annulation protocol for the preparation of indoline-C2,C3-fused N-heterocyclic scaffolds was described, in which available fluorinated N-arylhydroxylamines, activated alkynes, and ambident N-nucleophiles enabled a modular assembly of diverse indoline-C2,C3-fused N-heterocyclic scaffolds via an interrupted [3,3]-sigmatropic rearrangement of O-alkenyl-N-arylhydroxylamines under mild conditions. This protocol provides a mechanistically distinct and complementary alternative to the established methods for constructing C2,C3-fused indoline architectures.</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":"149190282","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
MPAThio Ligand-Accelerated Palladium-Catalyzed Nondirected Hydrogen Isotope Exchange of Arenes with D2O MPAThio配体加速钯催化芳烃与D2O的非定向氢同位素交换
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-13 DOI: 10.1021/acs.joc.6c01870
Yu Meng,Zhi-Jiang Jiang,Jiawei Han,Kenan Wang,Mengtao Zhu,Jian-Fei Bai,Jia Chen,Zhanghua Gao
{"title":"MPAThio Ligand-Accelerated Palladium-Catalyzed Nondirected Hydrogen Isotope Exchange of Arenes with D2O","authors":"Yu Meng,Zhi-Jiang Jiang,Jiawei Han,Kenan Wang,Mengtao Zhu,Jian-Fei Bai,Jia Chen,Zhanghua Gao","doi":"10.1021/acs.joc.6c01870","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01870","url":null,"abstract":"Hydrogen isotope exchange is an atom-economical strategy for accessing deuterium-labeled molecules, but its synthetic utility is often limited by slow exchange kinetics and poor reactivity of π-extended arenes. Herein, we report a palladium-catalyzed nondirected hydrogen isotope exchange (HIE) enabled by a dual-ligand combination of a monoprotected aminoethyl thioether (MPAThio) and an N-heteroarene ligand. This system exhibits faster HIE kinetics, reaching isotopic equilibrium within 30 min at 105 °C (and within 60 min at 90 °C), and enables efficient deuterium incorporation under mild conditions using D2O as the deuterium source. The protocol enables efficient deuteration of a broad range of mono- and multisubstituted arenes. For poorly soluble substrates relevant to organic light-emitting diode materials, a cosolvent strategy addresses solubility limitations, affording high deuterium incorporation. Mechanistic studies indicate that the MPAThio ligand lowers the barrier of accessing the reactive C–H activation manifold, thereby favoring efficient reversible HIE.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149152186","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
Synthesis of Pyrido[2,3-d]pyrimidin-4(3H)-ones via SNAr/Tandem Cyclization SNAr/串联环化法合成吡啶[2,3-d]嘧啶-4(3H)- 1
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-13 DOI: 10.1021/acs.joc.6c01296
Yu He,Wenquan Wang,Pengbo Zhu,Yaxing Guo,Hui Luo,Li Li,Lei Hua,Shanliang Ge,Longyu Li,Jinhui Yang
{"title":"Synthesis of Pyrido[2,3-d]pyrimidin-4(3H)-ones via SNAr/Tandem Cyclization","authors":"Yu He,Wenquan Wang,Pengbo Zhu,Yaxing Guo,Hui Luo,Li Li,Lei Hua,Shanliang Ge,Longyu Li,Jinhui Yang","doi":"10.1021/acs.joc.6c01296","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01296","url":null,"abstract":"A new method has been developed for constructing the pyrido[2,3-d]pyrimidin-4(3H)-one scaffold under metal- and ligand-free conditions. In this strategy, 2-bromo-N-phenylnicotinamide is activated by the synergistic electron-withdrawing effects of the pyridine ring and the amide group, enabling tandem nucleophilic aromatic substitution (SNAr)/cyclization with cyanamide or formamide under simple conditions. Control experiments and density functional theory (DFT) calculations support an SNAr/cyclization mechanism. Preliminary photophysical studies show that the products exhibit blue emission, suggesting potential applications in materials science. Additionally, molecular docking studies indicate that the synthesized scaffold may have relevance to medicinal chemistry, providing a foundation for future biological evaluations.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"167 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149152191","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
Photochemical Radical Cascade Annulation of 6-Azauracils Enabled by CsPbBr3 Perovskite Nanocrystals CsPbBr3钙钛矿纳米晶体对6-氮氧嘧啶的光化学自由基级联环化
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-13 DOI: 10.1021/acs.joc.6c01630
Pravat Nayek,Chidananda Biswal,Suman Kalyan Bishal,Sagnik Bhattacharya,Prasenjit Mal
{"title":"Photochemical Radical Cascade Annulation of 6-Azauracils Enabled by CsPbBr3 Perovskite Nanocrystals","authors":"Pravat Nayek,Chidananda Biswal,Suman Kalyan Bishal,Sagnik Bhattacharya,Prasenjit Mal","doi":"10.1021/acs.joc.6c01630","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01630","url":null,"abstract":"Direct annulation of 6-azauracils has remained challenging due to their strongly electron-deficient and decomposition-prone heterocyclic frameworks. This study presents unique insight into the core modification of the 6-azauracil system enabled by a CsPbBr3 perovskite nanocrystal-promoted photochemical cascade cyclization with an amino acid derivative. N-Phenylglycine, a zwitterion with strong surface binding affinity for the photocatalyst, generated a nucleophilic aminomethyl radical in dimethyl carbonate that added to the C═N bond, triggering a radical cascade to tetrahydroimidazole-fused triazines, structures of emerging relevance in biochemical applications. Dimethyl carbonate ensured radical stability and catalyst integrity, enabling a broad scope and late-stage functionalization. Beyond azauracils, the strategy also supports the late-stage functionalization of a range of biologically important drug molecules, providing a cost-effective, sustainable, and operationally simple platform for light-mediated synthesis empowered by perovskite nanocrystals.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"158 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149152195","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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