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Tunable Mono- or 1,1-Double Heck-type Coupling Reaction of Unconjugated Amido-alkenes with Remote Benzylic C(sp3)-H of N-Fluorobenzamides
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-12 DOI: 10.1039/d4qo01971g
Tianyu Lu, Lingyan Liu, Weixing Chang, Jing Li
{"title":"Tunable Mono- or 1,1-Double Heck-type Coupling Reaction of Unconjugated Amido-alkenes with Remote Benzylic C(sp3)-H of N-Fluorobenzamides","authors":"Tianyu Lu, Lingyan Liu, Weixing Chang, Jing Li","doi":"10.1039/d4qo01971g","DOIUrl":"https://doi.org/10.1039/d4qo01971g","url":null,"abstract":"This work described a tunable copper-catalyzed intermolecular oxidative functionalization reaction of unactivated alkenes directed by the remote benzylic free radical of the N-fluoroamides, and the corresponding monoalkylation and 1,1-bialkylation products of unactivated alkenes were obtained in good yields, respectively. These two reactions proceeded via a nitrogen-centered free radical generation of N-fluoroamide in the presence of copper salt, an intramolecular 1,5-hydrogen atom transfer, followed by the newly formed benzylic free radical addition across the alkenes, single-electron transfer, and β-hydride elimination multiple-steps sequential process, as represented a mono Heck-type coupling and a 1,1-double Heck-type coupling reaction of unactivated alkenes on the whole. These protocols showed good substrates scope and produced the polysubstituted alkenes, which could be further transformed to diverse structural molecules. Besides, the plausible reaction mechanism was proposed with the combination of density function theory calculation and control experiments.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"2 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142809772","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
Computational Studies on Mn(III)-Catalyzed Cyclopropanols: A Case of Mn(III)-Based Metalloradical Catalysis Involving α-Mn(II)-Bound-Alkyl Radical Key Intermediate
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-11 DOI: 10.1039/d4qo01775g
Pan Hong, Xiuyuan Zou, Pengcheng Zhang, Xin Lu, Long-Wu Ye, Yidong Luo, Qing Sun
{"title":"Computational Studies on Mn(III)-Catalyzed Cyclopropanols: A Case of Mn(III)-Based Metalloradical Catalysis Involving α-Mn(II)-Bound-Alkyl Radical Key Intermediate","authors":"Pan Hong, Xiuyuan Zou, Pengcheng Zhang, Xin Lu, Long-Wu Ye, Yidong Luo, Qing Sun","doi":"10.1039/d4qo01775g","DOIUrl":"https://doi.org/10.1039/d4qo01775g","url":null,"abstract":"Controlling the reactivity of radicals has long posed a significant challenge in the field of radical chemistry. A groundbreaking strategy to address this challenge involves the use of metal-entangled organic radicals via metalloradical catalysis (MRC). Despite achievements in this domain, the substrates capable of generating metal-bound radical species have predominantly been of an oxidative nature, with scarce reports on reductive substrates. Herein, using DFT calculations, we present a novel finding: a reducing substrate, cyclopropanol, capable of generating metal-bound radicals via Mn(acac)3 catalyst. Through detailed mechanistic exploration, we have determined that the free radical mechanism proposed in Mn(III)-catalyzed cyclopropanol reactions is energetically unfavorable, while the metal-bound radical mechanism can proceed smoothly at room temperature. Notably, the Mn(II)-bound carbene radical intermediate generated from cyclopropanol holds substantial potential for rational control over the diversity of radical reactions. Furthermore, the presence of metal-bound radical intermediates offers significant feasibility for designing stereoselective products by introducing auxiliary ligands in reactions involving cyclopropanols. This discovery highlights the potential of reducing substrates in metal-catalyzed radical reactions and unlocks new prospects for the development of redox-neutral radical catalytic processes. The ability to form well-defined metal-bound radicals from cyclopropanol not only expands the scope of substrates available for such transformations but also paves the way for advanced applications in stereoselective synthesis, leveraging the unique properties of metal coordination environments.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"38 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805187","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
Multichromophoric Perylene Iridium Triad as a Homogeneous Photocatalyst for the Efficient Synthesis of Tetrahydroquinoline Derivatives
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-11 DOI: 10.1039/d4qo02269f
Anita Kumari, Sanchita Sengupta
{"title":"Multichromophoric Perylene Iridium Triad as a Homogeneous Photocatalyst for the Efficient Synthesis of Tetrahydroquinoline Derivatives","authors":"Anita Kumari, Sanchita Sengupta","doi":"10.1039/d4qo02269f","DOIUrl":"https://doi.org/10.1039/d4qo02269f","url":null,"abstract":"This study presents the design and synthesis of a multichromophoric-catalyst system, namely, Ir-triad 1, which incorporates a perylene monoimide (PMI) as the central chromophore, with naphthalimide (NMI) positioned at its 1- and 7- bay positions and the catalyst features an iridium (Ir) metal ion coordinated with a cyclopentadienyl (Cp*) unit, a chloride ligand and a cyclometalating ligand attached to PMI. Following photophysical and electrochemical characterization, Ir-triad 1 was utilized as a homogeneous photocatalyst to efficiently synthesize tetrahydroquinolines from N, N-dimethylanilines and maleimides in an aerobic atmosphere. The reaction involves the direct cyclization via an sp³ C−H bond functionalization, yielding products in high yields from a diverse range of substrates, with up to 82-83% yield under blue LED (450 nm) irradiation.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"4 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142809774","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
Transformation of benzocorrole isomer into pyrrole-containing polycyclic molecules via copper-mediated cleavage and annulation
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-11 DOI: 10.1039/d4qo02145b
Biju Basumatary, Sawako Yada, Shunsuke Oka, Shigeki Mori, Tatsuya Mori, Tatsuki Abe, Daisuke Kawaguchi, Takuma Yasuda, Hiroyuki Furuta, Masatoshi Ishida
{"title":"Transformation of benzocorrole isomer into pyrrole-containing polycyclic molecules via copper-mediated cleavage and annulation","authors":"Biju Basumatary, Sawako Yada, Shunsuke Oka, Shigeki Mori, Tatsuya Mori, Tatsuki Abe, Daisuke Kawaguchi, Takuma Yasuda, Hiroyuki Furuta, Masatoshi Ishida","doi":"10.1039/d4qo02145b","DOIUrl":"https://doi.org/10.1039/d4qo02145b","url":null,"abstract":"We present the oxidative transformation of a corrole isomer, namely, dibenzocorrorin (<strong>3</strong>), featuring a modified connectivity pattern of bipyrrole moieties within the corrole scaffold, resulting in the formation of pyrrole-embedded polycyclic molecules (<strong>1</strong> and <strong>2</strong>). The X-ray crystallography analysis of compound <strong>1</strong> revealed the establishment of three C–N bonds through nitrogen sites in the pyrrole and indole rings, leading to a highly π-conjugated core with nine fused aromatic rings. Notably, the β-pyrrole protons of the diazadicyclopentaazulene moiety displayed significant high-field shifts in the <small><sup>1</sup></small>H-NMR spectrum, attributed to the 12π antiaromatic contribution of the diazadicyclopentaazulene segment, as indicated by NICS and ACID plot analyses. Compound <strong>1</strong> exhibited a broad near-infrared absorption beyond 1000 nm, a narrow electrochemical energy gap (Δ<em>E</em> = 1.15 V), a short excited-state lifetime, and stable photothermal conversion capability. The crystalline packing structure of <strong>1</strong>, characterized by a staircase-like stacking along the long axis of needle-shaped crystals, facilitated the fabrication of a single-crystal organic field-effect transistor. The resulting device demonstrated p-type semiconductor behaviour, emphasizing the potential of <strong>1</strong> in near-infrared optoelectronic applications.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"40 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142809773","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
Hierarchical Amplification of Chirality in Anion-Coordinated Tetrahedral Cages
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-11 DOI: 10.1039/d4qo02062f
Jie Zhao, Mingli Lian, Zijian Ni, Le Yu, Dong Yang
{"title":"Hierarchical Amplification of Chirality in Anion-Coordinated Tetrahedral Cages","authors":"Jie Zhao, Mingli Lian, Zijian Ni, Le Yu, Dong Yang","doi":"10.1039/d4qo02062f","DOIUrl":"https://doi.org/10.1039/d4qo02062f","url":null,"abstract":"Chirality is vital in asymmetric catalysis, biological systems, and materials science. However, the control of chiral transfer and amplification remains challenging but fascinating. Herein, we report the chirality transferred from the chiral carbon centers to the ‘aniono’ tetrahedral cages, which were constructed through the self-assembly of chiral C3-symmetric tris-bis(urea) ligands and oxoanions (PO43− or CO32−). The host-guest interaction can further alter the chirality, resulting in enhanced CD intensity accompanied by a redshift. Furthermore, anions have a great influence on the chiral behavior of the mixed-ligand (chiral and achiral ligand mixed in different proportions) cages due to the existence of structural transformation. Upon the self-assembly and subsequent host-guest chemistry, we establish a hierarchical chiral system at the supramolecular level, featuring controllable chiral transfer and amplification.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"77 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805135","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
[3+2] Cycloaddition Between Cyclic Diaryl λ3-Bromanes and Nitrones Towards the Formation of Dihydrobenzisoxazoles and An Evaluation of the Regioisomeric Bioactivity
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-10 DOI: 10.1039/d4qo02102a
Jing-Yi Fan, Ming-Chuan Wang, Jian-Feng Zhou, Tong-Qi Gan, Wan-Xuan Zhang, Wei Lin, Bin-Jie Li
{"title":"[3+2] Cycloaddition Between Cyclic Diaryl λ3-Bromanes and Nitrones Towards the Formation of Dihydrobenzisoxazoles and An Evaluation of the Regioisomeric Bioactivity","authors":"Jing-Yi Fan, Ming-Chuan Wang, Jian-Feng Zhou, Tong-Qi Gan, Wan-Xuan Zhang, Wei Lin, Bin-Jie Li","doi":"10.1039/d4qo02102a","DOIUrl":"https://doi.org/10.1039/d4qo02102a","url":null,"abstract":"Here the example of the efficient construction of important dihydrobenzisoxazole cores from the cycloaddition reactions between cyclic diaryl λ3-bromanes as the aryne precursors and nitrones is reported. Many dihydrobenzisoxazole-containing compounds were synthesized under transition-metal-free conditions, and this approach features a broad substrate scope, good functional group compatibility and reasonable regioselectivities. Preliminary bioactivity evaluations demonstrated that multiple examples of these dihydrobenzisoxazoles showed potential activities against porcine reproductive and respiratory syndrome virus (PRRSV).","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"82 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797362","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
Synthesis and antiproliferative activities of 2,3,5-trisubstituted 1H-pyrroles via formal [3+2] cycloaddition of 1-arylpropynes and nitriles 通过 1-arylpropynes 和腈的正规 [3+2] 环加成法合成 2,3,5-三取代的 1H 吡咯并提高其抗增殖活性
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-10 DOI: 10.1039/d4qo01999g
Dandan He, Ling Li, Xiong Wen, Luxiang Yin, Jue Li, Sha Wu, Huili Li, Fei Jiang, Xiangchun Shen
{"title":"Synthesis and antiproliferative activities of 2,3,5-trisubstituted 1H-pyrroles via formal [3+2] cycloaddition of 1-arylpropynes and nitriles","authors":"Dandan He, Ling Li, Xiong Wen, Luxiang Yin, Jue Li, Sha Wu, Huili Li, Fei Jiang, Xiangchun Shen","doi":"10.1039/d4qo01999g","DOIUrl":"https://doi.org/10.1039/d4qo01999g","url":null,"abstract":"A straightforward approach for the assemble of 2,3,5-trisubstituted 1H-pyrroles via a base-mediated [3+2] cycloaddition of 1-arylpropynes with nitriles has been reported through the alkali metal salts promoted C(sp3)-H functionalization. This reaction features transition metal-free catalyst, facile starting materials and wide substrate scope. Moreover, the biological evaluation revealed that these pyrrole products exhibit the antiproliferative activities of MDA-MB-231, SGC-7901, and HCT-116 cells, which provides a potential applications in pharmaceutical chemistry.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"3 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797514","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
Copper-Catalyzed Phosphorothiolation/Seleno(Telluro)phosphorylation of Vinylsulfonium Salts with P(III)-nucleophiles via the Insertion of Elemental Sulfur/Selenium/Tellurium
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-10 DOI: 10.1039/d4qo02154a
Biquan Xiong, Siya Zheng, Weifeng Xu, Yu Liu, Longzhi Zhu, Kewen Tang, Zelin Sun, Wai-Yeung Raymond Wong
{"title":"Copper-Catalyzed Phosphorothiolation/Seleno(Telluro)phosphorylation of Vinylsulfonium Salts with P(III)-nucleophiles via the Insertion of Elemental Sulfur/Selenium/Tellurium","authors":"Biquan Xiong, Siya Zheng, Weifeng Xu, Yu Liu, Longzhi Zhu, Kewen Tang, Zelin Sun, Wai-Yeung Raymond Wong","doi":"10.1039/d4qo02154a","DOIUrl":"https://doi.org/10.1039/d4qo02154a","url":null,"abstract":"A novel and facile copper-catalyzed phosphorothiolation and seleno(telluro)phosphorylation of vinylsulfonium salts with P(III)-nucleophiles for constructing C-Z-P(V) bonds (Z = S, Se, Te) by activating selenium, tellurium and sulfur powder in-situ has been established. The phosphorylation process in this system may involve the Michaelis-Arbuzov rearrangement as the initial step. Vinylsulfonium salts with various substituents and different types of P(III)-nucleophiles demonstrated excellent substrate suitability, resulting in the synthesis of the expected products with moderate to good yields. The model reaction is readily scalable to gram-level experiments under optimized conditions. Additionally, a possible mechanism for this transformation was proposed based on insights gained from stepwise control experiments and 31P NMR tracking experiments. To the best of our knowledge, this is the first method to activate inorganic tellurium in-situ using a phosphorylation source to form P-Te bonds directly. The P-Te compounds synthesized via this method exhibit superior activity against methicillin-resistant Staphylococcus aureus (MRSA).","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"20 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797515","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
Nickel-Catalyzed Reductive Difunctionalization of BN-heterocyclic Olefins
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-09 DOI: 10.1039/d4qo02032d
Chaokun Li, Kui Yu, Kai Yang, Qiuling Song
{"title":"Nickel-Catalyzed Reductive Difunctionalization of BN-heterocyclic Olefins","authors":"Chaokun Li, Kui Yu, Kai Yang, Qiuling Song","doi":"10.1039/d4qo02032d","DOIUrl":"https://doi.org/10.1039/d4qo02032d","url":null,"abstract":"The difunctionalization of olefins as an effective synthetic strategy has garnered significant attention among organic synthetic chemists, thus enabling complex molecular scaffolds to be assembled in a single step from readily accessible feedstock chemicals. Herein, a nickel-catalyzed reductive difunctionalization of BN-heterocyclic alkenes has been developed. A variety of BN-heterocycles were synthesized utilizing the specific characteristics of selected difunctionalization reactions, thereby facilitating the synthesis of a wider range of BN-heterocycles through further conversions and applications.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"18 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142793698","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
LuCl3/ZnI2 cocatalyzed 1,1-diborylation of terminal alkynes to 1,1-diborylalkenes with pinacolborane
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-09 DOI: 10.1039/d4qo01796j
Rongrong Zhou, Wenli Wang, Jianping Zhang, Qi Wang, Ziyan Chen, Yinlin Shao, Fangjun Zhang
{"title":"LuCl3/ZnI2 cocatalyzed 1,1-diborylation of terminal alkynes to 1,1-diborylalkenes with pinacolborane","authors":"Rongrong Zhou, Wenli Wang, Jianping Zhang, Qi Wang, Ziyan Chen, Yinlin Shao, Fangjun Zhang","doi":"10.1039/d4qo01796j","DOIUrl":"https://doi.org/10.1039/d4qo01796j","url":null,"abstract":"A method was developed using LuCl3/ZnI2 to cocatalyze the 1,1-diboration of simple terminal alkynes, producing from moderate-to-good yields of 1,1-diborylalkenes. Large-scale synthesis and further transformations indicate that this method has potential practical applications. Isotopic labeling experiments, and control experiments are used to elucidate the reaction mechanism.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"18 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142793704","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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