Jonas Bachmann, Andreas Drichel, Jonas Klopf, Abhishek Koner, Adam Slabon, Holger Helten
The use of dithieno- (DTDB) and difuro-4,6-dihydro-1,2,7-oxadiborepins (DFDB) as components of conjugated copolymers is demonstrated. Building upon our recently developed protocol for the modular synthesis of 5,5’-dibrominated difuro-4,6-dihydro-1,2,7-oxa- and azadiborepins, we devised a scalable route to the corresponding 5,5’-dibrominated and 5,5’-distannylated DTDB derivatives, which serve as monomers for subsequent polymerizations. Combining both the difunctionalized DTDB- and the DFDB-based monomers with electron-rich benzodithiophene (BDT) and electron-poor diketopyrrolopyrrole (DPP) building blocks, respectively, gave four new copolymers, which are well-soluble and fully air- and moisture-stable. They show broad absorptions over the visible spectral range – with the bands of the DPP-containing copolymers extending into the near-IR region. DFT calculations give further insights into the electronics of the copolymers. Photoelectrochemical measurements revealed that three of the new copolymers exhibit p-type while one of them exhibits n-type semiconducting behavior.
{"title":"Bifuran- and bithiophene-fused 4,6-dihydro-1,2,7-oxadiborepins as building blocks for conjugated copolymers","authors":"Jonas Bachmann, Andreas Drichel, Jonas Klopf, Abhishek Koner, Adam Slabon, Holger Helten","doi":"10.1039/d4qo01964d","DOIUrl":"https://doi.org/10.1039/d4qo01964d","url":null,"abstract":"The use of dithieno- (DTDB) and difuro-4,6-dihydro-1,2,7-oxadiborepins (DFDB) as components of conjugated copolymers is demonstrated. Building upon our recently developed protocol for the modular synthesis of 5,5’-dibrominated difuro-4,6-dihydro-1,2,7-oxa- and azadiborepins, we devised a scalable route to the corresponding 5,5’-dibrominated and 5,5’-distannylated DTDB derivatives, which serve as monomers for subsequent polymerizations. Combining both the difunctionalized DTDB- and the DFDB-based monomers with electron-rich benzodithiophene (BDT) and electron-poor diketopyrrolopyrrole (DPP) building blocks, respectively, gave four new copolymers, which are well-soluble and fully air- and moisture-stable. They show broad absorptions over the visible spectral range – with the bands of the DPP-containing copolymers extending into the near-IR region. DFT calculations give further insights into the electronics of the copolymers. Photoelectrochemical measurements revealed that three of the new copolymers exhibit p-type while one of them exhibits n-type semiconducting behavior.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"15 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142815549","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}
The Pd-catalyzed ring-forming reaction via multiple C─H activation provides an efficient strategy to access cyclic ring systems. The current reactions are primarily restricted to single and two-component reactions. Herein, we report a ring-forming reaction via palladium-catalyzed three-component multiple C─H activation. Using TsOMe as the methylating reagent, aryl iodides undergo maleimide-relayed C─H methylation. Subsequent cyclization via C(sp3)─H activation forms succinimide-fused tricyclic scaffolds. Depending on aryl iodides, the reaction involves dual or triple C─H activation to form two or three new C─C bonds. The reaction represents a new strategy for C─H methylation and offer a new synthetic method using simple and readily available substrates for succinimide-fused tricyclic scaffolds, which are crucial structural motifs found widely in organic compounds with diverse biological activities.
{"title":"Palladium-Catalyzed Three-Component Annulation Reaction Involving Multiple C─H Activation","authors":"Shuai Yang, Xiang Zuo, Yanghui Zhang","doi":"10.1039/d4qo01857e","DOIUrl":"https://doi.org/10.1039/d4qo01857e","url":null,"abstract":"The Pd-catalyzed ring-forming reaction via multiple C─H activation provides an efficient strategy to access cyclic ring systems. The current reactions are primarily restricted to single and two-component reactions. Herein, we report a ring-forming reaction via palladium-catalyzed three-component multiple C─H activation. Using TsOMe as the methylating reagent, aryl iodides undergo maleimide-relayed C─H methylation. Subsequent cyclization via C(sp3)─H activation forms succinimide-fused tricyclic scaffolds. Depending on aryl iodides, the reaction involves dual or triple C─H activation to form two or three new C─C bonds. The reaction represents a new strategy for C─H methylation and offer a new synthetic method using simple and readily available substrates for succinimide-fused tricyclic scaffolds, which are crucial structural motifs found widely in organic compounds with diverse biological activities.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"21 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142815547","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}
Jianyu Dong, Shaofeng Wu, Long Liu, Dan Zhou, Min Mo, Ya-Dong Gao, Lebin Su, Shuang-Feng Yin, Yongbo Zhou
A multiple-component oxidative cyclization of easily available 2-naphthols, anilines, and ethyl glyoxylate is successfully achieved using only molecular oxygen. The reaction enables green, efficient and highly selective synthesis of iminonaphthofuranones, a category of disperse dyes that are previously inaccessible. The products exhibit a wide spectrum of colors, adjustable from pale orange to dark purple. They are also readily transformed into naphthofuranones and highly functionalized naphthols.
{"title":"Iminonaphthofuranone synthesis via multiple-component cyclization of 2-naphthols using only molecular oxygen","authors":"Jianyu Dong, Shaofeng Wu, Long Liu, Dan Zhou, Min Mo, Ya-Dong Gao, Lebin Su, Shuang-Feng Yin, Yongbo Zhou","doi":"10.1039/d4qo01939c","DOIUrl":"https://doi.org/10.1039/d4qo01939c","url":null,"abstract":"A multiple-component oxidative cyclization of easily available 2-naphthols, anilines, and ethyl glyoxylate is successfully achieved using only molecular oxygen. The reaction enables green, efficient and highly selective synthesis of iminonaphthofuranones, a category of disperse dyes that are previously inaccessible. The products exhibit a wide spectrum of colors, adjustable from pale orange to dark purple. They are also readily transformed into naphthofuranones and highly functionalized naphthols.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"42 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142815548","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}
Jin Wang, Yaohui Liu, Jinhai Xu, Peiyuan Li, Xiaoxi Xu, Shuo Zhang, Jie Yang, Xianxiu Xu
We herein report a divergent synthesis of 2-CF₃ substituted quinolines and indoles via photoredox radical trifluoromethylation of ortho-vinylphenylisocyanides. This mild and green protocol offers a broad substrate scope and good functional group tolerance. Mechanistic investigations revealed that the trifluoromethyl radical is generated through an EDA complex between Togni’s reagent and a base under light irradiation.
{"title":"Photoredox trifluoromethylation of isocyanides to access 2-trifluoromethylated quinolines and indoles","authors":"Jin Wang, Yaohui Liu, Jinhai Xu, Peiyuan Li, Xiaoxi Xu, Shuo Zhang, Jie Yang, Xianxiu Xu","doi":"10.1039/d4qo02105c","DOIUrl":"https://doi.org/10.1039/d4qo02105c","url":null,"abstract":"We herein report a divergent synthesis of 2-CF₃ substituted quinolines and indoles via photoredox radical trifluoromethylation of ortho-vinylphenylisocyanides. This mild and green protocol offers a broad substrate scope and good functional group tolerance. Mechanistic investigations revealed that the trifluoromethyl radical is generated through an EDA complex between Togni’s reagent and a base under light irradiation.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"51 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142820725","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}
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.
{"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}
Pan Hong, Xiuyuan Zou, Pengcheng Zhang, Xin Lu, Long-Wu Ye, Yidong Luo, Qing Sun
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.
{"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}
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.
{"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}
We present the oxidative transformation of a corrole isomer, namely, dibenzocorrorin (3), featuring a modified connectivity pattern of bipyrrole moieties within the corrole scaffold, resulting in the formation of pyrrole-embedded polycyclic molecules (1 and 2). The X-ray crystallography analysis of compound 1 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 1H-NMR spectrum, attributed to the 12π antiaromatic contribution of the diazadicyclopentaazulene segment, as indicated by NICS and ACID plot analyses. Compound 1 exhibited a broad near-infrared absorption beyond 1000 nm, a narrow electrochemical energy gap (ΔE = 1.15 V), a short excited-state lifetime, and stable photothermal conversion capability. The crystalline packing structure of 1, 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 1 in near-infrared optoelectronic applications.
{"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}
Jie Zhao, Mingli Lian, Zijian Ni, Le Yu, Dong Yang
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.
{"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}
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).
{"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}
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