Organic Chemistry Frontiers最新文献_第10页

The construction of aromatic rings by photocatalytic radical-induced cyclization reactions 光催化自由基诱导环化反应构建芳环

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-06-04 DOI: 10.1039/d5qo00667h

Xi-Ni Luo, Dong-Qing Yang, Hong-Lin Wu, Jia-Yao Feng, Sheng Du, Yu He, Rongnan Yi, Jun-Qi Zhang, Keqi Tang, Wenting Wei

{"title":"The construction of aromatic rings by photocatalytic radical-induced cyclization reactions","authors":"Xi-Ni Luo, Dong-Qing Yang, Hong-Lin Wu, Jia-Yao Feng, Sheng Du, Yu He, Rongnan Yi, Jun-Qi Zhang, Keqi Tang, Wenting Wei","doi":"10.1039/d5qo00667h","DOIUrl":"https://doi.org/10.1039/d5qo00667h","url":null,"abstract":"Photocatalytic radical-induced cyclization reactions offer an efficient paradigm for constructing aromatic rings due to their unique environmental friendliness, independence from electronic effects, and high functional group tolerance. However, the high reactivity of intermediates in radical reactions, particularly the challenges of controlling it proceeds in an orderly manner according to the expected pathway and the reaction terminates after the ring is formed, which leads to diminished precision in the construction of aromatic rings. Compared to traditional cyclization methods for synthesizing aromatic rings, photocatalysis enables direct cleavage of high-bond-energy chemical bonds under mild conditions, eliminating the need for high temperature, high pressure, or stoichiometric oxidants. Furthermore, photocatalytic systems can serve as a bridge to connect multiple reaction steps, thereby streamlining the process and enhancing efficiency. Recently, significant progress has been made in applying photocatalytic radical-induced cyclization for the construction of aromatic rings. However, to date, there has been no comprehensive summary of this area reported. In this review, we try to provide a comprehensive perspective on the construction of aromatic rings via photocatalytic radical-induced cyclization. The discussion is organized into five sections based on the type of aromatic ring formed: monoheteroatom-doped aromatic rings, diheteroatom-doped aromatic rings, triheteroatom-doped aromatic rings, all-carbon aromatic ring, and non-classical aromatic rings. This review with a particular focus on elucidating reaction mechanisms, the synergistic effect of catalysts and light sources, and the applications of this strategy in pharmaceutical synthesis and materials science.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"17 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144211686","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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

Facile Synthesis of a Contorted Polycyclic Aromatic Hydrocarbon Derivative 一种扭曲多环芳烃衍生物的简易合成

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-06-04 DOI: 10.1039/d5qo00604j

Xiaoxia Duan, Kai Lan, Yue Su, Chuyang Cheng

引用次数: 0

Oligomeric Monoterpenoid Indole Alkaloids from the Flowers of Gelsemium elegans with Anti-inflammatory and Anti-fibrotic Activities 具有抗炎和抗纤维化活性的葛兰花低聚单萜类吲哚生物碱

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-06-03 DOI: 10.1039/d5qo00551e

Ji-Hong Gu, Ni-Ping Li, Hao-Ting Lin, Ling-Na Dai, Min-Jing Cheng, Jian Hong, Yi-Yi Li, Jun-Shan Liu, Wen-Cai Ye, Lei Wang

引用次数: 0

Dinickel-Catalyzed Regio- and Enantioselective α-Alkylation of Cyclic Ketones with Unactivated Alkyl Halides 镍催化环酮与非活化卤化烷基的区域和对映选择性α-烷基化反应

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-06-03 DOI: 10.1039/d5qo00448a

Liangwei Zhu, Lin Zhang, Jian Zhang, Peigen Wang, Ruopeng Bai, Zhonglin Tao

引用次数: 0

Remote Activating Strategy Enabled (RASE) π-Bond Migratory Dealkylative C-N coupling Utilising N-Fluorobenzenesulfonimide (NFSI) as A Bifunctional Domino Reagent 利用n -氟苯磺酰亚胺（NFSI）作为双功能多米诺试剂的远程激活策略激活(RASE) π键迁移脱烷基C-N偶联

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-06-03 DOI: 10.1039/d5qo00480b

Jiahao Gu, Zhenyang Wan, Yuhong Lu, Xiangmin Tian, Ziyue Zeng, Dailin Zhuang, Ziyuan Li

引用次数: 0

Chemodivergent Temperature Controlled Switchable Iron Catalysed Annulation of o-vinylaniline with Isatin Derivatives 化学发散温控可切换铁催化邻乙烯苯胺与Isatin衍生物的环化

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-06-02 DOI: 10.1039/d5qo00626k

Sakshi Singh, Samir Kumar Mondal, Shantanu Pal

引用次数: 0

NCI-driven regioselectivity and enantioreversal in chiral phosphoric acid-catalyzed arylamine functionalization nci驱动的手性磷酸催化芳胺功能化的区域选择性和对反性

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-06-02 DOI: 10.1039/d5qo00673b

Zi-Hao Li, Abing Duan, Shu-Yu Zhang

{"title":"NCI-driven regioselectivity and enantioreversal in chiral phosphoric acid-catalyzed arylamine functionalization","authors":"Zi-Hao Li, Abing Duan, Shu-Yu Zhang","doi":"10.1039/d5qo00673b","DOIUrl":"https://doi.org/10.1039/d5qo00673b","url":null,"abstract":"Non-covalent interactions (NCIs) have emerged as pivotal elements in asymmetric catalysis, enabling precise control over reactivity and selectivity in complex transformations. Despite their central role in designing catalytic systems, mechanistic understanding remains limited for reactions where NCIs concurrently govern regio- and enantioselectivity. The inherent complexity of CPA-catalyzed asymmetric reactions, characterized by diverse NCIs—particularly with arylamine substrates bearing multiple NCI-active motifs—presents formidable challenges for theoretical analysis and data-driven mechanistic modeling. This challenge becomes particularly pronounced when examining the enantioreversal phenomenon, where minute NCI perturbations orchestrate divergent catalytic pathways. Crucially, substrate-controlled enantioreversal operating independently of CPA groups modifications remain conspicuously undercharacterized in multi-selective reactions, particularly at the mechanistic level. In this study, we investigate three representative multi-site CPA-catalyzed asymmetric functionalizations of arylamines, utilizing detailed theoretical calculations to explore the influence of steric effects and NCIs, as well as the interplay between regioselectivity and enantioreversal. Our findings clarify the factors governing regioselectivity and enantioreversal, leading to a detailed elucidation of the mechanistic roles of key variables in existing frameworks. This work provides a robust theoretical foundation for optimizing CPA-catalyzed asymmetric reactions involving arylamines, while paving the way for future machine learning-driven advancements in this domain.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"163 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144193316","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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

NaH-Promoted One-Pot Oxidation/Aromatization and C-3H Chalcogenation of Indoline: Atmospheric Control-Based Selective Intermediates 钠促进吲哚的一锅氧化/芳构化和C-3H加硫：基于大气控制的选择性中间体

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-05-31 DOI: 10.1039/d5qo00576k

Suman Majee, Km. Anjali, Shailly Agarwal, Vishnu Poonia, Alok Kumar Singh, Biswajit Guchhait, Devalina Ray

{"title":"NaH-Promoted One-Pot Oxidation/Aromatization and C-3H Chalcogenation of Indoline: Atmospheric Control-Based Selective Intermediates","authors":"Suman Majee, Km. Anjali, Shailly Agarwal, Vishnu Poonia, Alok Kumar Singh, Biswajit Guchhait, Devalina Ray","doi":"10.1039/d5qo00576k","DOIUrl":"https://doi.org/10.1039/d5qo00576k","url":null,"abstract":"A sub-stoichiometric sodium hydride promoted strategy with diselenides and disulphides, has been devised for the one-pot cascade oxidation/arometization and regioselective C-3 selenium/sulfenylation of indolines under transition metal-free conditions. The newly introduced protocol facilitates the synthesis of C-3 chalcogenated indoles with exceptional flexibility and efficiency. The chalcogenation reaction was successfully performed under both aerobic and inert conditions leading to the formation of C-3 chalcogenated indoles via two different intermediates. The mechanistic insights were derived from various controlled experiments and trapping of reaction intermediates for both the conditions, structurally varifying them by spectral analysis. The preponderance of the radical route was validated by EPR spectroscopy and radical quenching experiments. A wide variety of 3-arylthioindoles and 3-arylselenylindoles containing electron-releasing and withdrawing substituents were obtained in high to excellent yields with this modest and environmentally benign protocol. Additionally, post-transformation of sulfenylated derivatives has further led to the generation of diarylsulfoxide core of pharmaceutical interest. The reaction is applicable to gram scale synthesis without significant loss in product yield, indicating its application for large-scale synthesis. Interestingly, the biological evaluation of the 5-bromo-3-((4-(trifluoromethyl)phenyl)selanyl)-1H-indole and 3-((4-chlorophenyl)thio)-1H-indole revealed significant activity against rapidly growing mycobacteria (RGM).","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"37 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144184090","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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

TFPN-Mediated Acyl Fluoride Platform: Efficient Synthesis of Esters, Thioesters, and Macrolactones from Carboxylic Acids with Diverse Nucleophiles tfpn介导的酰基氟化平台：由羧酸和各种亲核试剂高效合成酯、硫酯和大内酯

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-05-31 DOI: 10.1039/d5qo00651a

Dou Zhang, Peng Shen, Yao Zhang, Qiuyi Zheng, Jiahui Zhang, Chunyu Han, Silin Xu, Jinhua Yang

引用次数: 0

Acrolein Triftosylhydrazone: A Versatile Vinylcarbene Reagent 异丙二烯丙二烯丙二烯丙二烯丙二烯丙二烯丙二烯丙二烯丙二烯丙二烯丙二烯丙二烯丙二烯丙二烯丙二烯丙二烯丙二烯丙二烯丙二烯丙二烯丙二烯

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-05-31 DOI: 10.1039/d5qo00663e

Ying Gan, Jin Zhang, Karunanidhi Murali, Yongquan Ning, Yong Wu, Jacek Mlynarski, Zhaohong Liu

引用次数: 0