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Zinc-Promoted Reductive Thiolation of Sulfonated Alcohols to Access C(sp3)-Enriched Sulfides. 锌促进的磺化醇还原硫基化制备C（sp3）富集硫化物。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-07-03 DOI: 10.1021/acs.joc.5c00957
Yingjie Wu,Han Qian,Wenlei Zhang,Ting Ouyang,Ying Bai,Yuenian Xu,Xinxin Shao
{"title":"Zinc-Promoted Reductive Thiolation of Sulfonated Alcohols to Access C(sp3)-Enriched Sulfides.","authors":"Yingjie Wu,Han Qian,Wenlei Zhang,Ting Ouyang,Ying Bai,Yuenian Xu,Xinxin Shao","doi":"10.1021/acs.joc.5c00957","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00957","url":null,"abstract":"We report a Zn-mediated reductive cross-coupling of alkyl sulfonates with N-sulfenylsuccinimides or thiosulfonates for the efficient construction of C(sp3)-enriched sulfides. This method provides rapid access to structurally diverse unsymmetrical alkyl sulfides with broad functional group tolerance. The synthetic utility of this protocol is further demonstrated through scalable synthesis, late-stage modification of complex bioactive molecules, and downstream derivatizations. Preliminary mechanistic studies suggest the formation of a highly reactive zinc thiolate intermediate, generated from the reaction of Zn with the sulfur-transfer reagent. The in situ-formed zinc thiolates exhibit considerable nucleophilic reactivity for SN2-type thiolation of a series of primary and secondary alkyl sulfonates that are readily prepared from abundant alkyl alcohols.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"20 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144547761","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
Scalable DOS-like Strategy to the δ-Amino Acids via Petasis/Cross Metathesis Reactions Sequence 通过Petasis/Cross - meta反应序列获得δ-氨基酸的可扩展DOS-like策略
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-07-03 DOI: 10.1021/acs.joc.5c00620
Maksym V. Herasymchuk, Anastasiia V. Fedinchyk, Kostiantyn P. Melnykov, Eugeniy M. Ostapchuk, Tetiana V. Druzhenko, Dmytro M. Volochnyuk, Serhiy V. Ryabukhin
{"title":"Scalable DOS-like Strategy to the δ-Amino Acids via Petasis/Cross Metathesis Reactions Sequence","authors":"Maksym V. Herasymchuk, Anastasiia V. Fedinchyk, Kostiantyn P. Melnykov, Eugeniy M. Ostapchuk, Tetiana V. Druzhenko, Dmytro M. Volochnyuk, Serhiy V. Ryabukhin","doi":"10.1021/acs.joc.5c00620","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00620","url":null,"abstract":"A convenient and scalable approach to δ,δ-spirosubstituted δ-amino acids and their α,β-unsaturated analogues from bulk ketones was elaborated. The proposed routes include Petasis reaction of starting ketone with allylboronic acid pinacol ester and methanolic ammonia, and cross metathesis with acrylic acid derivatives as key steps. The developed protocols are novel, robust, and economically efficient. They avoid tedious separation and purification, can be scaled up to 40 g of final compounds and propose an efficient way to novel conformationally rigid foldamers.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"7 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144547927","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
Influence of Halogen Atoms and the Reactivity of Nucleophiles on Reactions of Tetrahydropyran and Tetrahydrofuran Acetals with C-Nucleophiles: Hyperconjugation and Inductive Effects. 卤素原子和亲核试剂的反应活性对四氢吡喃和四氢呋喃缩醛与c -亲核试剂反应的影响：超共轭和诱导效应。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-07-03 DOI: 10.1021/acs.joc.4c03128
Krystyna M Demkiw,Wouter A Remmerswaal,Asma Sheikh,Ibrahim N Sheikh,Collin H Witt,Jeroen D C Codée,K A Woerpel
{"title":"Influence of Halogen Atoms and the Reactivity of Nucleophiles on Reactions of Tetrahydropyran and Tetrahydrofuran Acetals with C-Nucleophiles: Hyperconjugation and Inductive Effects.","authors":"Krystyna M Demkiw,Wouter A Remmerswaal,Asma Sheikh,Ibrahim N Sheikh,Collin H Witt,Jeroen D C Codée,K A Woerpel","doi":"10.1021/acs.joc.4c03128","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03128","url":null,"abstract":"Tetrahydropyran acetals bearing a fluorine atom adjacent to the acetal carbon atom can undergo highly stereoselective substitution reactions with nucleophilic alkenes to give the 1,2-cis products. By contrast, the chlorine- and bromine-substituted acetals give the 1,2-trans products. These results can be understood by considering oxocarbenium ion intermediates and their conformational preferences, which are dictated by hyperconjugative effects from axial substituents, with F ≪ H < Cl < Br. Reactions of the corresponding five-membered-ring acetals are also 1,2-cis selective in the case of fluorine and 1,2-trans selective with chlorine- and bromine-substituted acetals, but selectivities showed different trends of reactivity vs selectivity. The reactions with the five-membered-ring acetal were interpreted as requiring anomeric halides as reactive intermediates because of the conditions required to obtain substitution products.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"5 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144547911","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
Copper(II)-Catalyzed Enantioselective Friedel-Crafts Alkylation Reactions of 1-Naphthols and Electron-Rich Phenols with Trifluoropyruvates. 铜（II）催化1-萘酚和富电子酚与三氟丙酮酸酯的对映选择性Friedel-Crafts烷基化反应。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-07-03 DOI: 10.1021/acs.joc.5c00112
Leipeng Xue,Jiaqi Yang,Lei He,Xinyu Hou,Mengxin Kan,Jiahui Li,Tianxu Yu,Chao Yao,Yue-Ming Li
{"title":"Copper(II)-Catalyzed Enantioselective Friedel-Crafts Alkylation Reactions of 1-Naphthols and Electron-Rich Phenols with Trifluoropyruvates.","authors":"Leipeng Xue,Jiaqi Yang,Lei He,Xinyu Hou,Mengxin Kan,Jiahui Li,Tianxu Yu,Chao Yao,Yue-Ming Li","doi":"10.1021/acs.joc.5c00112","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00112","url":null,"abstract":"By fine-tuning the electronic and steric properties of the chiral ligands, chiral Cu(II) complex-catalyzed enantioselective Friedel-Crafts alkylation/lactonization of 1-naphthols and electron-rich phenols with trifluoropyruvates provided the desired products with up to 99% ee and up to 99% yield. The reactions were carried out on a gram scale with low catalyst loading. Especially, the optically pure GABAB positive allosteric modulator (R)-BHFF was prepared using this protocol.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"12 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144547910","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
Amine-Controlled, Transition-Metal-Catalyzed Hydrodefluorination and Defluoroamination of Fluoroarenes with 8-Aminoquinoline as a Directing Group. 以8-氨基喹啉为导向基团的胺控制过渡金属催化氟芳烃的加氢脱氟和脱氟胺化。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-07-02 DOI: 10.1021/acs.joc.5c00361
Anjun Ding,Xiaoyong Liu,Ziyue Xu,Shiyu Lei,Wen Liu,Jie Jiang,Shunxin Li,Zhengjiang Fu,Shengmei Guo,Hu Cai
{"title":"Amine-Controlled, Transition-Metal-Catalyzed Hydrodefluorination and Defluoroamination of Fluoroarenes with 8-Aminoquinoline as a Directing Group.","authors":"Anjun Ding,Xiaoyong Liu,Ziyue Xu,Shiyu Lei,Wen Liu,Jie Jiang,Shunxin Li,Zhengjiang Fu,Shengmei Guo,Hu Cai","doi":"10.1021/acs.joc.5c00361","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00361","url":null,"abstract":"The selective defluorofunctionalization of fluoroarenes via transition-metal catalysis has garnered significant attention. This study presents an amine-controlled, directing-group-assisted strategy to achieve selective hydrodefluorination and defluoroamination of fluoroarenes. Dimethylamine enables the selective hydrodefluorination of fluoroarenes through β-hydride elimination from a nitro-centered nickel intermediate, while other amines furnish the defluoroamination reactions. In hydrodefluorination, dimethylformamide (DMF) serves a dual role as both the solvent and the source of dimethylamine. These reactions demonstrate high selectivity and a broad substrate scope.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"19 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144533601","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
Ag-Catalyzed Formal [2 + 4] Cycloaddition for the Diastereoselective Synthesis of Sterically Hindered 4-Aminochroman-2-ones from α-Diazopyrazoleamides and o-Hydroxy Aldimines. 由α-重氮吡唑酰胺和邻羟基醛胺催化银催化正[2 + 4]环加成非对映选择性合成空间位阻4-氨基铬-2-酮。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-07-02 DOI: 10.1021/acs.joc.5c00747
Pei Li,Maoqing Shi,Kaixin Yang,Kongxi Qiu,Zhonghui Zhang,Yaxin Li,Xiaoyan Yang,Xiang Fu,Ji Zhang,Wenhao Hu,Yu Qian
{"title":"Ag-Catalyzed Formal [2 + 4] Cycloaddition for the Diastereoselective Synthesis of Sterically Hindered 4-Aminochroman-2-ones from α-Diazopyrazoleamides and o-Hydroxy Aldimines.","authors":"Pei Li,Maoqing Shi,Kaixin Yang,Kongxi Qiu,Zhonghui Zhang,Yaxin Li,Xiaoyan Yang,Xiang Fu,Ji Zhang,Wenhao Hu,Yu Qian","doi":"10.1021/acs.joc.5c00747","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00747","url":null,"abstract":"4-Aminochroman-2-one derivatives serve as crucial scaffolds in numerous pharmaceuticals and bioactive compounds. Here, we describe an efficient Ag-catalytic [2 + 4] cycloaddition reaction between α-diazo pyrazoleamides and o-hydroxy aromatic aldimines for the rapid synthesis of substituted 4-aminochroman-2-one derivatives with high yield and excellent diastereoselectivity. This method features a broad substrate scope, mild reaction conditions, and the ability to generate products exhibiting notable antitumor activity against selected tumor cell lines.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"70 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144547913","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
Frustrated Lewis Acid-Catalyzed C-N Coupling for the Stereoselective Synthesis of Nucleoside Analogs. Lewis酸催化的C-N偶联在核苷类似物立体选择性合成中的应用。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-07-02 DOI: 10.1021/acs.joc.5c01238
Tanner L McMinn,Nathan E DeSousa,Ian M Mou,Michel R Gagné
{"title":"Frustrated Lewis Acid-Catalyzed C-N Coupling for the Stereoselective Synthesis of Nucleoside Analogs.","authors":"Tanner L McMinn,Nathan E DeSousa,Ian M Mou,Michel R Gagné","doi":"10.1021/acs.joc.5c01238","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01238","url":null,"abstract":"β-N-glycosides serve as essential building blocks for constructing nucleic acid residues, and their altered forms are ubiquitous among many natural products and pharmacophores. However, the most commonly employed N-glycosylation procedures still require aggressive Lewis acid catalysts, multistep procedures to glycosyl donors, or precious metal catalysts to obviate typical catalyst quenching from basic N-nucleophiles. Here, we report a straightforward FLP-based catalytic approach for forming β-N-glycosides, emphasizing efficiency and mild conditions. We show that catalytic quantities of BCF can facilitate stereoselective N-glycosylations, coupling common pyran- and furan-based donors with various silylated N-heterocycles. The straightforward application of our N-glycosylation procedure to relevant medicinal targets was additionally shown and bodes well for the broad application of this method.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144533544","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-Promoted Thioetherification Reactions via Electron Donor-Acceptor Complexes between Active Esters and Sulfinates. 可见光促进的活性酯和亚硫酸盐之间通过电子供体-受体配合物的硫醚化反应。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-07-02 DOI: 10.1021/acs.joc.5c00949
Xiao Xu,Qin-Hua Song
{"title":"Visible-Light-Promoted Thioetherification Reactions via Electron Donor-Acceptor Complexes between Active Esters and Sulfinates.","authors":"Xiao Xu,Qin-Hua Song","doi":"10.1021/acs.joc.5c00949","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00949","url":null,"abstract":"Visible-light-promoted thioetherification reactions occur via electron donor-acceptor (EDA) complexes between tetrachloro-N-hydroxyphthalimide esters (TCNHPI esters) and sulfinates. A series of alkyl aryl thioesters were obtained in yields of up to 85% across 38 cases. The measurement of association constant (KEDA = 584 M-1) shows very strong interaction in the EDA complex. The mechanism has been demonstrated by isolated byproducts, radical capture, UV/vis absorption, and fluorescence spectral measurements. The protocol provides a new facile approach for the synthesis of sulfides with odorless sulfinates in a mild condition.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"27 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144547914","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
Vinyl-to-Acyl 1,5-Palladium Shift Enabled Amidation and Esterification of Aldehydes. 乙烯基-酰基1,5-钯移位使醛的酰胺化和酯化。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-07-02 DOI: 10.1021/acs.joc.5c01114
Yaru Fang,Qifan Guan,Meiyu Chen,Shan Yuan,Xueliang Huang
{"title":"Vinyl-to-Acyl 1,5-Palladium Shift Enabled Amidation and Esterification of Aldehydes.","authors":"Yaru Fang,Qifan Guan,Meiyu Chen,Shan Yuan,Xueliang Huang","doi":"10.1021/acs.joc.5c01114","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01114","url":null,"abstract":"We report an unprecedented synthetic route to dihydrobenzofuran and indoline acyl compounds via vinyl-to-acyl 1,5-palladium migration. This transformation is initiated by alkyne insertion, triggering the key 1,5-palladium migration to generate reactive acyl palladium intermediates. These intermediates undergo efficient trapping by amines and alcohols to afford the corresponding amide and ester-type products. Notably, the product can be further elaborated to construct eight-membered lactam scaffolds with significant pharmaceutical potential, highlighting the broad utility of this strategy in complex molecule synthesis.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"27 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144533600","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 Column Chromatography-Free Protocol for the Synthesis of Water-Soluble Cavitands. 水溶性空腔体合成的无柱色谱方法。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-07-02 DOI: 10.1021/acs.joc.5c00725
Gabriele Zirpoli,Manuel Petroselli
{"title":"A Column Chromatography-Free Protocol for the Synthesis of Water-Soluble Cavitands.","authors":"Gabriele Zirpoli,Manuel Petroselli","doi":"10.1021/acs.joc.5c00725","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00725","url":null,"abstract":"An efficient synthetic protocol for the synthesis of a library of unprecedented resorcin[4]arene-based water-soluble molecular containers is reported here. Key to this approach is the tetra-iodo derivative 3, named \"Key Iodo Cavitand\" (KIC), which acts as a concave-shaped scaffold for the synthesis of deep-cavitands via Sonogashira coupling. Most of the deep-cavitands described in this study are synthesized without chromatographic processes, leading to a faster purification, ready accessibility, and easier scale-up, while also offering a different cavity in terms of size and shape compared to the current ones. Preliminary binding experiments on cyclodecane as a model guest are reported in D2O, while DFT calculations confirm the encapsulation of fullerene derivatives such as C60 and C70, highlighting the potential of the proposed molecular containers.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"48 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144547915","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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