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Recent advances in phosphine-mediated sequential annulations 膦介导序贯环的最新进展
IF 9.4 1区 化学
Chinese Chemical Letters Pub Date : 2024-11-09 DOI: 10.1016/j.cclet.2024.110628
Xuling Pan, Wei Cai, You Huang
{"title":"Recent advances in phosphine-mediated sequential annulations","authors":"Xuling Pan,&nbsp;Wei Cai,&nbsp;You Huang","doi":"10.1016/j.cclet.2024.110628","DOIUrl":"10.1016/j.cclet.2024.110628","url":null,"abstract":"<div><div>Polycyclic compounds are widely found in natural products and drug molecules with important biological activities, which attracted the attention of many chemists. Phosphine-catalyzed nucleophilic addition is one of the most powerful tools for the construction of various cyclic compounds with the advantages of atom economy, mild reaction conditions and simplicity of operation. Allenolates, Morita−Baylis−Hillman (MBH) alcohols and their derivatives (MBHADs), electron-deficient olefins and alkynes are very efficient substrates in phosphine mediated annulations, which formed many phosphonium species such as <em>β</em>-phosphonium enolates, <em>β</em>-phosphonium dienolates and vinyl phosphonium ylides as intermediates. This review describes the reactivities of these phosphonium zwitterions and summarizes the synthesis of polycycle compounds through phosphine-mediated intramolecular and intermolecular sequential annulations. Thus, a systematic summary of the research process based on the phosphine-mediated sequential annulations of allenolates, MBH alcohols and MBHADs, electron-deficient olefins and alkynes are presented in Chapters 2–6, respectively.</div></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"36 5","pages":"Article 110628"},"PeriodicalIF":9.4,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143550232","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
Stable radicals in bacteria composites hybridized by a doubly-strapped perylene diimide for near-infrared photothermal conversion 双链苝二亚胺杂化细菌复合材料中用于近红外光热转换的稳定自由基
IF 9.4 1区 化学
Chinese Chemical Letters Pub Date : 2024-11-09 DOI: 10.1016/j.cclet.2024.110627
Jingjing Zhang , Fei Yang , Liying Zhang , Ran Li , Guo Wang , Yanqing Xu , Wei Wei
{"title":"Stable radicals in bacteria composites hybridized by a doubly-strapped perylene diimide for near-infrared photothermal conversion","authors":"Jingjing Zhang ,&nbsp;Fei Yang ,&nbsp;Liying Zhang ,&nbsp;Ran Li ,&nbsp;Guo Wang ,&nbsp;Yanqing Xu ,&nbsp;Wei Wei","doi":"10.1016/j.cclet.2024.110627","DOIUrl":"10.1016/j.cclet.2024.110627","url":null,"abstract":"<div><div>Radical anions of electron-deficient perylene diimides (PDI) are attractive near-infrared (NIR) absorbers for photothermal conversion; however, their stability is often compromised by strong aggregation and reoxidation in air. Herein, we present a class of bacterial composites hybridized with a newly synthesized doubly-strapped PDI cyclophane, termed “Gemini Box” (<strong>GBox-3<sup>4+</sup></strong>), which features air-stable PDI radicals for NIR photothermal conversion. The effective spatial isolation provided by the double-sided cationic molecular straps allows <strong>GBox-3<sup>4+</sup></strong> to completely suppress chromophore aggregation, even in concentrated aqueous solutions up to 2 mmol/L, thereby preserving its characteristic fluorescence for live-cell imaging. After incubation of bacteria with <strong>GBox-3<sup>4+</sup></strong>, the radical species PDI<sup>•–</sup> have been found to stably exist in the bacterial composites under ambient conditions, both in aqueous suspension and solid forms. Further experiments demonstrate that the air stability of the radical species relies on the simultaneous presence of the doubly-strapped PDI dye and the bacteria. Moreover, the dye-bacterial composites exhibited an high-efficiency NIR photothermal effect with high durability, enabling their application as photothermal agents for seawater desalination. This work provides a new access to the <em>in situ</em> fabrication of photothermal materials from biomass, relying on the rational molecular design and the unique microenvironment of bacteria.</div></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"36 7","pages":"Article 110627"},"PeriodicalIF":9.4,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143895914","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
Polymer microparticles with ultralong room-temperature phosphorescence for visual and quantitative detection of oxygen through phosphorescence image and lifetime analysis 具有超长室温磷光的聚合物微颗粒,通过磷光图像和寿命分析用于氧的视觉和定量检测
IF 9.4 1区 化学
Chinese Chemical Letters Pub Date : 2024-11-09 DOI: 10.1016/j.cclet.2024.110629
Zeyin Chen, Jiaju Shi, Yusheng Zhou, Peng Zhang, Guodong Liang
{"title":"Polymer microparticles with ultralong room-temperature phosphorescence for visual and quantitative detection of oxygen through phosphorescence image and lifetime analysis","authors":"Zeyin Chen,&nbsp;Jiaju Shi,&nbsp;Yusheng Zhou,&nbsp;Peng Zhang,&nbsp;Guodong Liang","doi":"10.1016/j.cclet.2024.110629","DOIUrl":"10.1016/j.cclet.2024.110629","url":null,"abstract":"<div><div>Room-temperature phosphorescence (RTP) materials exhibiting long emission lifetimes have gained increasing attention owing to their potential applications in encryption, anti-counterfeiting, and sensing. However, most polymers exhibit a short RTP lifetime (&lt;1 s) because of their unstable triplet excitons. Herein, a new strategy of polymer chain stabilized phosphorescence (PCSP), which yields a new kind of RTP polymers with an ultralong lifetime and a sensitive oxygen response, has been reported. The rigid polymer chains of poly(methyl mathacrylate) (PMMA) immobilize the emitter molecules through multiple interactions between them, giving rise to efficient RTP. Meanwhile, the loosely-packed amorphous polymer chains allow oxygen to diffuse inside, endowing the doped polymers with oxygen sensitivity. Flexible and transparent polymer films exhibited an impressive ultralong RTP lifetime of 2.57 s at room temperature in vacuum, which was among the best performance of PMMA. Intriguingly, their RTP was rapidly quenched in the presence of oxygen. Furthermore, RTP microparticles with a diameter of 1.63 μm were synthesized using <em>in situ</em> dispersion polymerization technique. Finally, oxygen sensors for quick, visual, and quantitative oxygen detection were developed based on the RTP microparticles through phosphorescence lifetime and image analysis. With distinctive advantages such as an ultralong lifetime, oxygen sensitivity, ease of fabrication, and cost-effectiveness, PCSP opens a new avenue to sensitive materials for oxygen detection.</div></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"36 5","pages":"Article 110629"},"PeriodicalIF":9.4,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143487379","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
Double redox-mediated intrinsic semiconductor photocatalysis: Practical semi-heterogeneous synthesis 双氧化还原介导的本征半导体光催化:实用的半非均相合成
IF 9.4 1区 化学
Chinese Chemical Letters Pub Date : 2024-11-08 DOI: 10.1016/j.cclet.2024.110621
Xin He , Feng Liu , Tao Tu
{"title":"Double redox-mediated intrinsic semiconductor photocatalysis: Practical semi-heterogeneous synthesis","authors":"Xin He ,&nbsp;Feng Liu ,&nbsp;Tao Tu","doi":"10.1016/j.cclet.2024.110621","DOIUrl":"10.1016/j.cclet.2024.110621","url":null,"abstract":"","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"36 3","pages":"Article 110621"},"PeriodicalIF":9.4,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143318349","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
Review on near-infrared absorbing/emissive carbon dots: From preparation to multi-functional application 近红外吸收/发射碳点研究进展:从制备到多功能应用
IF 9.4 1区 化学
Chinese Chemical Letters Pub Date : 2024-11-07 DOI: 10.1016/j.cclet.2024.110618
Yupeng Liu , Hui Wang , Songnan Qu
{"title":"Review on near-infrared absorbing/emissive carbon dots: From preparation to multi-functional application","authors":"Yupeng Liu ,&nbsp;Hui Wang ,&nbsp;Songnan Qu","doi":"10.1016/j.cclet.2024.110618","DOIUrl":"10.1016/j.cclet.2024.110618","url":null,"abstract":"<div><div>Carbon dots (CDs) are an emerging class of zero-dimensional carbon nano optical materials that are as promising candidates for various applications. Through the exploration of scientific researchers, the optical band gap of CDs has been continuously regulated and red-shifted from the initial blue-violet light to longer wavelengths. In recent years, CDs with near-infrared (NIR) absorption/emission have been gradually reported. Because NIR light has deeper penetration and lower scattering and is invisible to the human eye, it has great application prospects in the fields of biological imaging and treatment, information encryption, optical communications, <em>etc</em>. Although there are a few reviews on deep red to NIR CDs, they only focus on the single biomedical direction. There is still a lack of comprehensive reviews focusing on NIR (≥700 nm) absorption and luminescent CDs and their multifunctional applications. Based on our research group's findings on NIR CDs, this review summarizes recent advancements in their preparation strategies and applications, points out the current shortcomings and challenges, and anticipates future development trajectories.</div></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"36 5","pages":"Article 110618"},"PeriodicalIF":9.4,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143487364","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
Fluorine-functionalized zirconium-organic cages for efficient photocatalytic oxidation of thioanisole 氟功能化锆有机笼高效光催化氧化硫代苯甲醚
IF 9.4 1区 化学
Chinese Chemical Letters Pub Date : 2024-11-06 DOI: 10.1016/j.cclet.2024.109934
Jia-Ru Li , Ning Li , Li-Ling He , Jun He
{"title":"Fluorine-functionalized zirconium-organic cages for efficient photocatalytic oxidation of thioanisole","authors":"Jia-Ru Li ,&nbsp;Ning Li ,&nbsp;Li-Ling He ,&nbsp;Jun He","doi":"10.1016/j.cclet.2024.109934","DOIUrl":"10.1016/j.cclet.2024.109934","url":null,"abstract":"<div><div>Zirconium-based metal-organic cages (Zr-MOCs) typically exhibit high stability, but their structural and application reports are scarce due to stringent crystallization conditions. We have successfully fluorinated the classical Zr-MOCs (<strong>ZrT-3</strong>) for the first time, obtaining the fluorinated MOCs (<strong>ZrT-3-F</strong>). Notably, <strong>ZrT-3-F</strong> not only inherits the high stability of its parent structure, but also acts as a catalyst for the effective oxidation of benzyl thioether for the first time. The reaction can reach a conversion rate of 99 % in 6 h, and the selectivity reaches 95 %, which far exceeds the non-fluorinated <strong>ZrT-3</strong>. This work proves that the specific functionalization of the classical Zr-MOCs can further expand their application potential, such as catalysis.</div></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"36 1","pages":"Article 109934"},"PeriodicalIF":9.4,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142592883","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
Engineering eg filling of RuO2 enables a robust and stable acidic water oxidation 工程上如充注RuO2,使酸性水氧化稳定而有力
IF 9.4 1区 化学
Chinese Chemical Letters Pub Date : 2024-11-05 DOI: 10.1016/j.cclet.2024.110612
Qing Li , Yumei Feng , Yingjie Yu , Yazhou Chen , Yuhua Xie , Fang Luo , Zehui Yang
{"title":"Engineering eg filling of RuO2 enables a robust and stable acidic water oxidation","authors":"Qing Li ,&nbsp;Yumei Feng ,&nbsp;Yingjie Yu ,&nbsp;Yazhou Chen ,&nbsp;Yuhua Xie ,&nbsp;Fang Luo ,&nbsp;Zehui Yang","doi":"10.1016/j.cclet.2024.110612","DOIUrl":"10.1016/j.cclet.2024.110612","url":null,"abstract":"<div><div>Efficient and stable electrocatalyst for oxygen evolution reaction (OER) in acidic environment is vital for polymer electrolyte membrane water electrolysis (PEMWE). In this work, we have devised the formation of heterostructured RuO<sub>2</sub>/MnO<sub>2</sub> with nanoflower structure for acidic OER catalysis. Compared to commercial RuO<sub>2</sub>, the overpotential at 50 mA/cm<sup>2</sup> is decreased by 36 mV, corresponding to a 3.7-fold better mass activity. The boosted acidic OER performance is attributed to the heterostructure inducing more electrons are filled in e<sub>g</sub> orbital of Ru atom triggering a better deprotonation of bridge oxygen atom in Ru-O<sub>bri</sub>-Mn structure evidenced by pH-independent cyclic voltammetry test. Moreover, RuO<sub>2</sub>/MnO<sub>2</sub> sustains its acidic OER activity within 20 h, longer than commercial RuO<sub>2</sub>. The membrane electrode assembly (MEA) test suggests than only 2.18 V is required to achieve a current density of 5 A/cm<sup>2</sup>. The theoretical calculation reveals that the e<sub>g</sub> filling of Ru atom is increased from 2.18 to 2.39 after MnO<sub>2</sub> incorporation, reducing the energy for the formation of *OOH moiety.</div></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"36 3","pages":"Article 110612"},"PeriodicalIF":9.4,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143318380","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
Graphene-supported isolated platinum atoms and platinum dimers for CO2 hydrogenation: Catalytic activity and selectivity variations 石墨烯负载的分离铂原子和铂二聚体用于CO2加氢:催化活性和选择性变化
IF 9.4 1区 化学
Chinese Chemical Letters Pub Date : 2024-11-05 DOI: 10.1016/j.cclet.2024.110611
Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang
{"title":"Graphene-supported isolated platinum atoms and platinum dimers for CO2 hydrogenation: Catalytic activity and selectivity variations","authors":"Sanmei Wang ,&nbsp;Dengxin Yan ,&nbsp;Wenhua Zhang ,&nbsp;Liangbing Wang","doi":"10.1016/j.cclet.2024.110611","DOIUrl":"10.1016/j.cclet.2024.110611","url":null,"abstract":"<div><div>Manipulating catalyst structures to control product selectivity while maintaining high activity presents a considerable challenge in CO<sub>2</sub> hydrogenation. Combining density functional theory calculations and microkinetic analysis, we proposed that graphene-supported isolated Pt atoms (Pt<sub>1</sub>/graphene) and Pt<sub>2</sub> dimers (Pt<sub>2</sub>/graphene) exhibited distinct selectivity in CO<sub>2</sub> hydrogenation. Pt<sub>1</sub>/graphene facilitated the conversion of CO<sub>2</sub> into formic acid, whereas Pt<sub>2</sub>/graphene favored methanol generation. The variation in product selectivity arose from the synergistic interaction of Pt<sub>2</sub> dimers, which facilitated the migration of H atoms between two Pt atoms and promoted the transformation from *COOH intermediates to *C(OH)<sub>2</sub> intermediates, altering the reaction pathways compared to isolated Pt atoms. Additionally, an analysis of the catalytic activities of three Pt<sub>1</sub>/graphene and three Pt<sub>2</sub>/graphene structures revealed that the turnover frequencies for formic acid generation on Pt<sub>1ii</sub>/graphene and methanol generation on Pt<sub>2i</sub>/graphene were as high as 744.48 h<sup>-1</sup> and 789.48 h<sup>-1</sup>, respectively. These values rivaled or even surpassed those previously reported in the literature under identical conditions. This study provides valuable insights into optimizing catalyst structures to achieve desired products in CO<sub>2</sub> hydrogenation</div></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"36 4","pages":"Article 110611"},"PeriodicalIF":9.4,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143149443","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
Construction of sintering-resistant gold catalysts via ascorbic-acid inducing strong metal-support interactions 通过抗坏血酸诱导强金属-载体相互作用构建抗烧结金催化剂
IF 9.4 1区 化学
Chinese Chemical Letters Pub Date : 2024-11-04 DOI: 10.1016/j.cclet.2024.110608
Yunxia Liu , Guandong Wu , Lin Li , Yiming Niu , Bingsen Zhang , Botao Qiao , Junhu Wang
{"title":"Construction of sintering-resistant gold catalysts via ascorbic-acid inducing strong metal-support interactions","authors":"Yunxia Liu ,&nbsp;Guandong Wu ,&nbsp;Lin Li ,&nbsp;Yiming Niu ,&nbsp;Bingsen Zhang ,&nbsp;Botao Qiao ,&nbsp;Junhu Wang","doi":"10.1016/j.cclet.2024.110608","DOIUrl":"10.1016/j.cclet.2024.110608","url":null,"abstract":"<div><div>Maintaining high metal dispersion of supported metal catalysts to achieve superior reactivity under harsh conditions poses one of the main challenges for their practical applications. Constructing and regulating the strong metal-support interactions (SMSI) by diverse methodologies has emerged as one of the promising approaches to fabricating robust supported metal catalysts. In this study, we report an <span>l</span>-ascorbic acid (AA)-inducing strategy to generate SMSI on a titania-supported gold (Au) catalyst after high-temperature treatment in an inert atmosphere (600 °C, N2). The AA-induced SMSI can efficiently stabilize Au nanoparticles (NPs) and preserve their catalytic performance. The detailed study reveals that the key to realizing this SMSI is the generation of oxygen vacancies within the TiO<sub>2</sub> support induced by the adsorbed AA, which drives the formation of the TiO<sub><em>x</em></sub> permeable layer onto the Au NPs. The strategy could be extended to TiO<sub>2</sub>-supported Au catalysts with different crystal phases and platinum group metals, such as Pt, Pd, and Rh. This work offers a promising novel route to design stable and efficient supported noble metal catalysts by constructing SMSI using simple reducing organic adsorbent.</div></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"36 4","pages":"Article 110608"},"PeriodicalIF":9.4,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143149390","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
Green synthesis of 2-trifluoromethylquinoline skeletons via organocatalytic N-[(α-trifluoromethyl)vinyl]isatins CN bond activation 有机催化N-[(α-三氟甲基)乙烯基]isatins CN键活化绿色合成2-三氟甲基喹啉骨架
IF 9.4 1区 化学
Chinese Chemical Letters Pub Date : 2024-11-03 DOI: 10.1016/j.cclet.2024.110598
Cong-Bin Ji , Ding-Xiong Xie , Mei Chen , Ye-Ying Lan , Bao-Hua Zhang , Ji-Ying Yang , Zheng-Hui Kang , Shu-Jie Chen , Yu-Wei Zhang , Yun-Lin Liu
{"title":"Green synthesis of 2-trifluoromethylquinoline skeletons via organocatalytic N-[(α-trifluoromethyl)vinyl]isatins CN bond activation","authors":"Cong-Bin Ji ,&nbsp;Ding-Xiong Xie ,&nbsp;Mei Chen ,&nbsp;Ye-Ying Lan ,&nbsp;Bao-Hua Zhang ,&nbsp;Ji-Ying Yang ,&nbsp;Zheng-Hui Kang ,&nbsp;Shu-Jie Chen ,&nbsp;Yu-Wei Zhang ,&nbsp;Yun-Lin Liu","doi":"10.1016/j.cclet.2024.110598","DOIUrl":"10.1016/j.cclet.2024.110598","url":null,"abstract":"<div><div>The Pfitzinger reaction has long served as a notable synthesis pathway for quinoline-4-carboxylic acids. Although recognized for its synthetic potential since its discovery &gt;138 years ago, a truly catalytic variant has remained elusive until now. Herein, we present a novel 2‑<em>tert</em>‑butyl‑1,1,3,3-tetramethylguanidine (BTMG)-catalyzed Pfitzinger reaction that employs <em>N</em>-[(α-trifluoromethyl)vinyl]isatins with amines and alcohols, providing direct routes to 2-CF<sub>3</sub>-quinoline-4-carboxamides and carboxylic esters. This method is not only green and environmentally benign but also accommodates the introduction of other functional groups like CF<sub>2</sub>H and CO<sub>2</sub>Me at the C2 position of quinoline skeleton. The utility of this methodology was demonstrated by the broad substrate scope, the late-stage modification of commercial drugs, and the diverse derivatization of quinoline framework. More importantly, this work not only opens up a new avenue for the activation of amide C<img>N bonds in catalytic reaction development, but also unlocks the huge potential of some 2-trifluoromethyl quinolines with strong inhibitory activity against PTP1B or optoelectronic application in organic light-emitting diodes.</div></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"36 7","pages":"Article 110598"},"PeriodicalIF":9.4,"publicationDate":"2024-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143895983","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
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