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Water-Mediated Electrochemical Sulfonylation of Alkynes: Switchable Access to Alkynyl versus Alkenyl Sulfones. 水介导的炔基电化学磺酰化：炔基与烯基砜的可切换性。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01796
Ziyan Gu, Feng Zhao, Bin Song, Yiwen Hao, Bingcheng Hu, Chong Zhang
{"title":"Water-Mediated Electrochemical Sulfonylation of Alkynes: Switchable Access to Alkynyl versus Alkenyl Sulfones.","authors":"Ziyan Gu, Feng Zhao, Bin Song, Yiwen Hao, Bingcheng Hu, Chong Zhang","doi":"10.1021/acs.joc.6c01796","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01796","url":null,"abstract":"<p><p>A novel electrochemical oxidative sulfonylation method has been established for the selective, sustainable synthesis of alkynyl and alkenyl sulfones from alkynes and thiophenols. In this method, water serves as both the hydrogen and oxygen sources, while the current intensity and the water dosage can be readily tuned to control the reaction outcome. Importantly, the transformation proceeds under mild conditions without the use of metal catalysts or hazardous oxidants. The protocol also exhibits broad substrate scope and excellent functional-group compatibility. Mechanistic investigations support a radical-mediated pathway, and the practical utility of the method was further demonstrated by gram-scale synthesis.</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":"149177934","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
Base-Promoted Hydrophosphorylation of Enaminones for the Synthesis of Geminal Phosphoryl Amino Ketones. 碱促进胺酮氢磷酸化合成双磷基氨基酮。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01748
Gengxin Li, Quanquan Zhou, Xi Li, Jie-Ping Wan
{"title":"Base-Promoted Hydrophosphorylation of Enaminones for the Synthesis of Geminal Phosphoryl Amino Ketones.","authors":"Gengxin Li, Quanquan Zhou, Xi Li, Jie-Ping Wan","doi":"10.1021/acs.joc.6c01748","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01748","url":null,"abstract":"<p><p>The direct hydrophosphorylation reaction of NH-enaminones has been achieved by simple base promotion with diaryl phosphine oxides as reaction partners. The synthesis of divergent β-phosphoryl-β-amino ketones has been allowed under mild heating (30 °C) in a green medium of 2-methyl tetrahydrofuran (2-MeTHF) without employing any metal reagent.</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":"149190284","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
Nonconventional Liquid Crystals with a Helicene-Containing Core: Synthesis, Columnar Mesomorphism, Photoluminescence, and Electron Conductivity. 含螺旋烯核的非常规液晶：合成、柱状介形、光致发光和电子导电性。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01332
Bing Yan, Yu Luo, Chong-Yang Zeng, Hui-Min Pan, Xiao-Yan Bai, Bo Xiao, Ke-Qing Zhao, Bertrand Donnio
{"title":"Nonconventional Liquid Crystals with a Helicene-Containing Core: Synthesis, Columnar Mesomorphism, Photoluminescence, and Electron Conductivity.","authors":"Bing Yan, Yu Luo, Chong-Yang Zeng, Hui-Min Pan, Xiao-Yan Bai, Bo Xiao, Ke-Qing Zhao, Bertrand Donnio","doi":"10.1021/acs.joc.6c01332","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01332","url":null,"abstract":"<p><p>Nonconventional mesogens featuring a [5]helicene aromatic core (i.e., 11,20-difluorotribenzo[c,k,m]naphtho[1,2-f]tetraphene, BNAn) were synthesized by two successive BuLi-assisted SNAr reactions in good yields. These tandem reactions involve an initial SNAr reaction between perfluorobenzene (C6F6) and racemic 2,2'-dibromo-1,1'-binaphthalene, followed by a second SNAr reaction with lipophilic 2,2'-dibromo-1,1'-biphenyls, respectively. These Janus-like mesogens, bearing four alkoxy chains only, exhibit exceptionally rich columnar-based mesomorphism, ranging from Colhex and Colrec to LamColrec mesophases via increasing chain-length over wide temperature ranges, extending down to room temperature. They emit light at 450 nm with a 27% quantum yield in solution, and their solid-film electron mobility reaches ca. 10-3 cm2/V s. These findings highlight the promise of these novel helicene-inspired mesogens for advanced optoelectronic thin-film devices.</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":"149177879","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
Palladium-Catalyzed Cascade 5-exo-dig Annulation and Amination for Assembly of Amino-Functionalized Trisubstituted Furans. 钯催化级联5-外环化和胺化组装氨基功能化三取代呋喃。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c02023
Qiang Tang, Shuwen Kong, Wangcheng Hu, Suolan Zheng, Xiaochun Jiang, Yongjia Shang, Xinwei He
{"title":"Palladium-Catalyzed Cascade 5-exo-dig Annulation and Amination for Assembly of Amino-Functionalized Trisubstituted Furans.","authors":"Qiang Tang, Shuwen Kong, Wangcheng Hu, Suolan Zheng, Xiaochun Jiang, Yongjia Shang, Xinwei He","doi":"10.1021/acs.joc.6c02023","DOIUrl":"https://doi.org/10.1021/acs.joc.6c02023","url":null,"abstract":"<p><p>A novel route for the preparation of trisubstituted furans with an amino functional group is presented as a palladium-catalyzed cascade 5-exo-dig annulation/amination reaction of α-alkynyl-α,β-enones with N-hydroxybenzamides. The reaction proceeds through a cascade sequence of intramolecular 5-exo-dig annulation, amination, Lossen rearrangement, and decarboxylation, forming two new C-X (X = O, N) bonds in a one-step transformation. This cascade protocol features a wide substrate range and outstanding functional group compatibility and allows an efficient large-scale synthesis and downstream transformations of the target products.</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":"149177916","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
Visible-Light-Driven C-H Arylation of Aminoquinones with Diaryliodonium Salts. 氨基醌类与二芳基碘鎓盐的可见光驱动C-H芳化反应。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01717
Anam Nawaz, Shaozhong Wang
{"title":"Visible-Light-Driven C-H Arylation of Aminoquinones with Diaryliodonium Salts.","authors":"Anam Nawaz, Shaozhong Wang","doi":"10.1021/acs.joc.6c01717","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01717","url":null,"abstract":"<p><p>A visible-light-driven C-H arylation of 2-amino-1,4-naphthoquinones with diaryliodonium salts has been developed using 10-phenylphenothiazine (PTH) as a photocatalyst. Mechanistic studies reveal that aminoquinone serves both as the substrate and as an electron shuttle in the electron transfer from PTH to the diaryliodonium salts. The combination of this photo-driven C-H arylation with an intramolecular SNAr cyclization provides a streamlined route to carbazolequinone scaffolds, significantly facilitating the synthesis of medicinally relevant tetracyclic 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":"149177977","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
Engineering IntramolecularHydrogen Bond Networksto Access Ensembles of Conformational Isomers of 24-Atom Macrocycles:Computation Corroborates Assignments and Predicts Structure 工程分子内氢键网络访问24原子大环构象异构体的集成：计算确证分配和预测结构
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c01634
Liam E. Claton,K. Harsha Vardhan Reddy,Eric E. Simanek
{"title":"Engineering Intramolecular\u0000Hydrogen Bond Networks\u0000to Access Ensembles of Conformational Isomers of 24-Atom Macrocycles:\u0000Computation Corroborates Assignments and Predicts Structure","authors":"Liam E. Claton,K. Harsha Vardhan Reddy,Eric E. Simanek","doi":"10.1021/acs.joc.6c01634","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01634","url":null,"abstract":"Abstract Intramolecular hydrogen bond (IMHB) networks contribute to the shape and physical properties of macrocycles. Understanding and ultimately engineering these networks represents a challenge to the field, both experimentally and computationally. Here, 24-atom triazine macrocycles are used as a model system to probe how a competing IMHB network can influence ensemble populations. Substitution distant from the macrocycle backbone offers an opportunity for introducing a competitive hydrogen bond donor. In its absence, incorporating symmetric and unsymmetric 2° amines leads to one and three persistent conformational isomers, respectively. Incorporation of a 1° amine leads to a competing IMHB network. Five persistent conformational isomers are observed. Computation corroborates assignment of the known conformers and predicts the structure of the emergent isomer: An expanded hinge conformer joins the hinge and non-hinge shapes previously reported. Corroborating evidence comes from H/D exchange of a methylene group on the macrocycle backbone, allowing for interpretation of a critical region of the 1H NMR spectrum. This five-conformer ensemble appears to be independent of the 1° amine chosen based on evidence obtained from 13C NMR spectra.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"30 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149210342","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
A Water-Soluble Molecular Tweezer Xanthone Receptor for Carboxylates and Nucleotide Bases. 羧酸盐和核苷酸碱基的水溶性分子镊子型山酮受体。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-15 DOI: 10.1021/acs.joc.6c00815
Irene Boya Del Teso, Estela Sánchez-Santos, Ángel L Fuentes de Arriba, Francisca Sanz, José J Garrido-González, Joaquín R Morán
{"title":"A Water-Soluble Molecular Tweezer Xanthone Receptor for Carboxylates and Nucleotide Bases.","authors":"Irene Boya Del Teso, Estela Sánchez-Santos, Ángel L Fuentes de Arriba, Francisca Sanz, José J Garrido-González, Joaquín R Morán","doi":"10.1021/acs.joc.6c00815","DOIUrl":"https://doi.org/10.1021/acs.joc.6c00815","url":null,"abstract":"<p><p>Carboxylate groups are widely present in biomolecules, and they play an important role as key building blocks in organic chemistry. In this work, a new water-soluble molecular receptor for carboxylates, based on the xanthone skeleton decorated with naphthalene units acting as molecular tweezers, is reported. The xanthone skeleton provides linear NH bonds emulating the geometry found in many hydrolases, while the molecular tweezer scaffold creates the hydrophobic region, which allows the association of hydrophobic guests in water. X-ray diffraction studies for some receptor intermediates prove the right geometry of the oxyanion hole, where the combination of hydrogen bonds with the hydrophobic cavity has allowed the association of carboxylates as well as nucleotide bases in water with association constants up to 476 M-1.</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":"149190245","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 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
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