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Regioselective, Lewis Acid-Catalyzed Ring-Openings of 2,3-Aziridyl Alcohols with Azoles 区域选择性路易斯酸催化2,3-氮基醇与偶氮的开环反应
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-25 DOI: 10.1021/acs.joc.5c00380
Benjamin Zheng, Mark S. Taylor
{"title":"Regioselective, Lewis Acid-Catalyzed Ring-Openings of 2,3-Aziridyl Alcohols with Azoles","authors":"Benjamin Zheng, Mark S. Taylor","doi":"10.1021/acs.joc.5c00380","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00380","url":null,"abstract":"Methods for regioselective ring-opening reactions of <i>N</i>-sulfonyl-protected aziridyl alcohols with azole nucleophiles have been developed. Several classes of azoles, including indazole, substituted pyrazole, benzotriazole, and tetrazole, have been employed as reaction partners, giving rise to C3-selective opening and &gt;3:1 <i>N</i>-selectivity. BF<sub>3</sub>•OEt<sub>2</sub> is the optimal catalyst for most substrate combinations, although examples where diphenylborinic acid (Ph<sub>2</sub>BOH) provides higher yields, or where the reactions proceed efficiently without a catalyst, are also described. Computational modeling of the BF<sub>3</sub>•OEt<sub>2</sub>-catalyzed reaction is consistent with the observed regiochemical outcome. The calculated ring-opening transition state appears to be stabilized by an unconventional OH···FB hydrogen-bonding interaction.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"53 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143876179","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
Asymmetric Synthesis of Tetrahydrofurans with Vicinal Stereocenters by RhII/RuII Relay Catalysis 邻立体中心四氢呋喃的不对称合成
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-25 DOI: 10.1021/acs.joc.5c00324
Xuejiao Li, Fang-Jie Liu, Baihua Ye
{"title":"Asymmetric Synthesis of Tetrahydrofurans with Vicinal Stereocenters by RhII/RuII Relay Catalysis","authors":"Xuejiao Li, Fang-Jie Liu, Baihua Ye","doi":"10.1021/acs.joc.5c00324","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00324","url":null,"abstract":"CpRu-catalyzed asymmetric allylic alkylation serves as a versatile synthetic tool but remains underexplored. Herein, we report a relay system combining achiral Rh<sub>2</sub>(OAc)<sub>4</sub> and a chiral pyridine-oxazoline-ligated Cp*Ru catalyst for asymmetric coupling of cinnamyl chlorides with diazo esters, generating silyl enol ethers <i>in situ</i> as key nucleophilic intermediates. This strategy affords chiral tetrahydrofuran derivatives with two vicinal stereocenters. Catalyst compatibility, excellent regioselectivity, and good enantioselectivity highlight its potential. Computational studies reveal the crucial role of Ru-centered chirality in reaction control.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"69 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872846","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
Total Synthesis of the Melodinus Alkaloid (±)-Melohemsine K 龙葵生物碱的全合成（±）-龙葵肽K
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-25 DOI: 10.1021/acs.joc.5c00545
Shanhao Lin, Hao Jing, Jinbo Duan, Jing Fang, Gaoyuan Zhao, Xingang Xie, Huilin Li, Xuegong She
{"title":"Total Synthesis of the Melodinus Alkaloid (±)-Melohemsine K","authors":"Shanhao Lin, Hao Jing, Jinbo Duan, Jing Fang, Gaoyuan Zhao, Xingang Xie, Huilin Li, Xuegong She","doi":"10.1021/acs.joc.5c00545","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00545","url":null,"abstract":"The first total synthesis of the novel <i>Melodinus</i> alkaloid melohemsine K is described in five steps from known precursors. The key reaction of the synthesis is a tandem enamine formation/retro-aza-Michael reaction/Diels–Alder cycloaddition/intramolecular lactamization reaction cascade between indole-fused azepine and aldehyde precursors, forging the critical CDE tricyclic system. The synthesis provided a general approach to novel <i>Melodinus</i> alkaloids.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"12 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872918","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-Catalyzed and 1,3-Sulfonyl Migration Enabled Installation of Azaindoles in the Periphery of Aryl Rings: Synthesis of Sulfonylated Pyrrolo[2,3-b]quinolines and Investigation of Antimalarial Potency 铜催化和1,3-磺酰基迁移使氮杂吲哚在芳基环外围的安装：磺化吡咯[2,3-b]喹啉的合成和抗疟效力的研究
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-24 DOI: 10.1021/acs.joc.5c00170
Shivani Choudhary, Gayyur, Siddhant, Ashan Manhas, Ruchir Kant, Nayan Ghosh
{"title":"Copper-Catalyzed and 1,3-Sulfonyl Migration Enabled Installation of Azaindoles in the Periphery of Aryl Rings: Synthesis of Sulfonylated Pyrrolo[2,3-b]quinolines and Investigation of Antimalarial Potency","authors":"Shivani Choudhary, Gayyur, Siddhant, Ashan Manhas, Ruchir Kant, Nayan Ghosh","doi":"10.1021/acs.joc.5c00170","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00170","url":null,"abstract":"Herein, an atom efficient and one-pot protocol, offering a series of sulfonylated pyrrolo[2,3-<i>b</i>]quinolines via C–N, C–C, and C–S bond formation, has been developed with an inexpensive copper catalyst. Notably, the reaction proceeds via a double-annulation reaction followed by a 1,3-sulfonyl migration sequence. Moreover, the method is applicable to a broad range of 2-carbonylanilines. Furthermore, synthetic applications and the scale-up reaction highlight the utility potential of this protocol. In addition, the antimalarial property of sulfonylated pyrrolo[2,3-<i>b</i>]quinolines showed parasite inhibition without cytotoxic effects in mammalian cells.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"75 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872920","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-Catalyzed Reductive Hydroamination of Alkenes and 1,3-Dienes with Nitroarenes 铜催化烯烃和1,3-二烯与硝基芳烃的还原氢胺化反应
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-24 DOI: 10.1021/acs.joc.4c02150
Zi-Heng Zhang, Shuang-Shuang Ma, Yuan-Yuan Jiang, Jin-Qing Lin, Bao-Hua Xu
{"title":"Copper-Catalyzed Reductive Hydroamination of Alkenes and 1,3-Dienes with Nitroarenes","authors":"Zi-Heng Zhang, Shuang-Shuang Ma, Yuan-Yuan Jiang, Jin-Qing Lin, Bao-Hua Xu","doi":"10.1021/acs.joc.4c02150","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02150","url":null,"abstract":"In this study, copper-catalyzed reductive hydroamination of alkenes and 1,3-dienes with nitroarenes was developed. Such umpolung hydroamination of unsaturated C═C double bonds exhibited Markovnikov selectivity, and the hydroamination of 1,3-dienes preferred 1,2-addition. Mechanistic studies suggested the system proceeds through a radical pathway with the concomitant activation of both substrates to nucleophilic alkyl radical species and electrophilic nitro-based intermediates, respectively. The attack of alkyl radical species on the N atom of nitro-based intermediates yielded the desired amines. However, this C–N cross-coupling strongly competed with the self-reduction of each species under such a system.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"8 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143867137","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
Mechanosynthesis of β-Naphthol Derivatives via Triflic Anhydride-Mediated Reaction of Arylacetic Acids with Arylalkynes 三酸酐介导芳基乙酸与芳基炔的机械合成β-萘酚衍生物
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-24 DOI: 10.1021/acs.joc.5c00204
Xu-Ling Xia, Liang Li, Jun-Shen Chen, Li-Feng Guo, Guan-Wu Wang
{"title":"Mechanosynthesis of β-Naphthol Derivatives via Triflic Anhydride-Mediated Reaction of Arylacetic Acids with Arylalkynes","authors":"Xu-Ling Xia, Liang Li, Jun-Shen Chen, Li-Feng Guo, Guan-Wu Wang","doi":"10.1021/acs.joc.5c00204","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00204","url":null,"abstract":"The mechanosynthesis of β-naphthol derivatives was accomplished through triflic anhydride-mediated cyclization reactions of arylacetic acids with arylalkynes in moderate to good yields by ball milling at room temperature. The present protocol featured solvent-free and simple conditions, a short reaction time, and easily available and inexpensive reagents.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"7 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143867058","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
Halogen Bonding Promoted Photoinduced Synthesis of 3,3-Disubstituted Oxindoles 卤素键促进3,3-二取代氧吲哚的光诱导合成
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-24 DOI: 10.1021/acs.joc.4c02963
Kun-Quan Chen, Jia Zhang, Xiao-Bo Chen, De-Qun Sun
{"title":"Halogen Bonding Promoted Photoinduced Synthesis of 3,3-Disubstituted Oxindoles","authors":"Kun-Quan Chen, Jia Zhang, Xiao-Bo Chen, De-Qun Sun","doi":"10.1021/acs.joc.4c02963","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02963","url":null,"abstract":"A photoinduced and catalyst-free radical cyclization process for the synthesis of 3,3-disubstituted oxindoles is reported. This method utilizes readily available α-bromoanilides as substrates, showcasing a broad substrate scope. The reaction mechanism is facilitated by a photoactivated charge transfer complex based on the halogen bonding of α-bromoanilide with TMG and alcohol.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"69 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872919","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
PhICl2/KSeCN Mediated Synthesis of Selenopheno[3,2-b]indoles and 3-Selenocyanato-2-benzoselenophene Indoles from 1,3-Diynes via Double Electrophilic Cyclization PhICl2/KSeCN介导1,3-二炔双亲电环合成硒酚[3,2-b]吲哚和3-硒氰酸酯-2-苯并硒酚吲哚
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1021/acs.joc.4c0318010.1021/acs.joc.4c03180
Jianing Zhang, Fengxia Sun, Xiangyu Zhan and Yunfei Du*, 
{"title":"PhICl2/KSeCN Mediated Synthesis of Selenopheno[3,2-b]indoles and 3-Selenocyanato-2-benzoselenophene Indoles from 1,3-Diynes via Double Electrophilic Cyclization","authors":"Jianing Zhang,&nbsp;Fengxia Sun,&nbsp;Xiangyu Zhan and Yunfei Du*,&nbsp;","doi":"10.1021/acs.joc.4c0318010.1021/acs.joc.4c03180","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03180https://doi.org/10.1021/acs.joc.4c03180","url":null,"abstract":"<p >A hypervalent iodine-enabled double intramolecular electrophilic cyclization of 1,3-diynes has been employed in the synthesis of selenopheno[3,2-<i>b</i>]indoles and 3-selenocyanato-2-benzoselenophene indoles. A plausible mechanism involving the <i>in situ</i> formation of the reactive Cl-SeCN species from the reaction of PhICl<sub>2</sub> and KSeCN, followed by cascade cyclization involving C–N/C–Se bond formations, was postulated.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"6063–6072 6063–6072"},"PeriodicalIF":3.3,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894277","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
Photocatalytic Approach Toward the Synthesis of Amides via S–C Cleavage: A Mild Approach S-C裂解光催化合成酰胺的温和方法
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1021/acs.joc.5c00230
Shikha Pandey, Sandeep Kumar, Vishal Singh, Vandana Srivastava, Sundaram Singh
{"title":"Photocatalytic Approach Toward the Synthesis of Amides via S–C Cleavage: A Mild Approach","authors":"Shikha Pandey, Sandeep Kumar, Vishal Singh, Vandana Srivastava, Sundaram Singh","doi":"10.1021/acs.joc.5c00230","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00230","url":null,"abstract":"A metal-free photocatalytic methodology for the synthesis of amides has been developed using eosin Y as a photocatalyst under ambient conditions. This approach provides a sustainable and efficient alternative for amide formation by eliminating the need for metal catalysts, and operates efficiently at room temperature. The use of eosin Y promotes high selectivity and reactivity, providing a green and cost-effective pathway for the synthesis of amides.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"11 5 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143862628","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
The Importance of Atomic Charges for Predicting Site-Selective Ir-, Ru-, and Rh-Catalyzed C–H Borylations 原子电荷对预测选择性Ir、Ru和rh催化的碳氢硼化反应的重要性
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1021/acs.joc.5c00343
Shannon M. Stephens, Kyle M. Lambert
{"title":"The Importance of Atomic Charges for Predicting Site-Selective Ir-, Ru-, and Rh-Catalyzed C–H Borylations","authors":"Shannon M. Stephens, Kyle M. Lambert","doi":"10.1021/acs.joc.5c00343","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00343","url":null,"abstract":"A supervised machine learning model has been developed that allows for the prediction of site selectivity in late-stage C–H borylations. Model development was accomplished using literature data for the site-selective (≥95%) C–H borylation of 189 unique arene, heteroarene, and aliphatic substrates that feature a total of 971 possible sp<sup>2</sup> or sp<sup>3</sup> C–H borylation sites. The reported experimental data was supplemented with additional chemoinformatic descriptors, computed atomic charges at the C–H borylation sites, and data from parameterization of catalytically active tris-boryl complexes resulting from the combination of seven different Ir-, Ru-, and Rh-based precatalysts with eight different ligands. Of the over 1600 parameters investigated, the computed atomic charges (e.g., Hirshfeld, ChelpG, and Mulliken charges) on the hydrogen and carbon atoms at the site of borylation were identified as the most important features that allow for the successful prediction of whether a particular C–H bond will undergo a site-selective borylation. The overall accuracy of the developed model was 88.9% ± 2.5% with precision, recall, and F1 scores of 92–95% for the nonborylating sites and 65–75% for the sites of borylation. The model was demonstrated to be generalizable to molecules outside of the training/test sets with an additional validation set of 12 electronically and structurally diverse systems.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"20 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143867135","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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