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Mechanochemical Decarbonylative Transformation of Amide Group to OCF3 and CF3 Functionalities under Ruthenium Catalysis 钌催化下酰胺基向 OCF3 和 CF3 官能团的机械化学脱羰基转化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-14 DOI: 10.1039/d4qo01946f
Satenik Mkrtchyan, Vishal B. Purohit, Oleksandr Shalimov, Michał Jakubczyk, Gabriela Addová, Juraj Filo, Barbora Benicka, Ronak V. Prajapati, Vaibhav D. Prajapati, Jiří Zapletal, Yevhen Karpun, Vitaliy Yepishev, Jarmila Kmeťová, Elena Kupcová, Viktor Iaroshenko
{"title":"Mechanochemical Decarbonylative Transformation of Amide Group to OCF3 and CF3 Functionalities under Ruthenium Catalysis","authors":"Satenik Mkrtchyan, Vishal B. Purohit, Oleksandr Shalimov, Michał Jakubczyk, Gabriela Addová, Juraj Filo, Barbora Benicka, Ronak V. Prajapati, Vaibhav D. Prajapati, Jiří Zapletal, Yevhen Karpun, Vitaliy Yepishev, Jarmila Kmeťová, Elena Kupcová, Viktor Iaroshenko","doi":"10.1039/d4qo01946f","DOIUrl":"https://doi.org/10.1039/d4qo01946f","url":null,"abstract":"A novel strategy has been introduced for the selective activation of N–C(O) moiety in primary aromatic amides through the utilization of pyrylium tetrafluoroborate under mechanochemical conditions, where the amide group undergoes subsequent activation and selectively substituted with the CF3 or OCF3 functionality. The scope of the present protocol includes selective transformation of diversely substituted aromatic amides to the respective trifluoromethyl and trifluoromethoxy arenes via mechanochemically induced deaminative functionalization under the synergy of a piezoelectric material barium titanate (BaTiO3), and ruthenium-catalysis. The presented mechanochemical approach unlocks new chemical spaces in pharmaceutical industries with a perspective on PASE (pot, atom, and step economy) synthesis.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"24 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142820724","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
Stereocontrolled desymmetrization of 2,5-cyclohexadienones via organocatalytic domino sulfa-1,6-/1,4-addition or sulfa-1,6- /1,4-/sulfa-1,4-addition reactions 通过有机催化多米诺磺胺-1,6-/1,4-加成或磺胺-1,6-/1,4-/磺胺-1,4-加成反应实现 2,5-Cyclohexadienones 的立体可控非对称化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-14 DOI: 10.1039/d4qo02097a
Vanisha Sodhi, Deepak Sharma, Manisha Sharma, Pankaj Chauhan
{"title":"Stereocontrolled desymmetrization of 2,5-cyclohexadienones via organocatalytic domino sulfa-1,6-/1,4-addition or sulfa-1,6- /1,4-/sulfa-1,4-addition reactions","authors":"Vanisha Sodhi, Deepak Sharma, Manisha Sharma, Pankaj Chauhan","doi":"10.1039/d4qo02097a","DOIUrl":"https://doi.org/10.1039/d4qo02097a","url":null,"abstract":"We have developed a desymmetrization of 2,5-cyclohexadienones tethered 3-cyano-4-styrylcoumarins via the amino-squaramide catalyzed initial regio-/enantio-selective sulfa-1,6-addition to the 3-cyano-4-styrylcoumarin moiety of the substrate, followed by an intramolecular vinylogous 1,4-addition to the dienone portion. An additional sulfa-Michael addition was observed when the thiols were taken in excess to create an additional stereogenic center. With our divergent approach, the two unique classes of hydrophenanthrene skeletons have been synthesized as single diastereoisomers in good to excellent yields and enantioselectivities (up to >99.5:0.5 er).","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"336 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142823300","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
Cyclizative Dearomative Rearrangement of Pyridines with Isocyanates
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-14 DOI: 10.1039/d4qo02111h
Xing-Zi Li, Fang-Zhou Li, Zi-Qi Wang, Hua Wu
{"title":"Cyclizative Dearomative Rearrangement of Pyridines with Isocyanates","authors":"Xing-Zi Li, Fang-Zhou Li, Zi-Qi Wang, Hua Wu","doi":"10.1039/d4qo02111h","DOIUrl":"https://doi.org/10.1039/d4qo02111h","url":null,"abstract":"Dearomatizationof pyridines is a robust synthetic method to access aza-heterocycles. Simultaneously, intermolecular cyclizative rearrangement is a recently developed new strategy toward efficiently constructing tetrasubstituted carbons. Here, we show that an effective integration of dearomatization approach with strategic cyclizative rearrangement render 2-acyl-substituted pyridines and their analogues with common isocyanates to undergo a tandem [3+2] heteroannulation followed by an extensive 1,2-carbon shift, thus providing a straightforward access to readily functionalized bicyclohydantoins. Based on the promotion of organophosphorus, different types of migrating groups, such as ester, amide, aryl and trifluoromethyl groups, are all well-tolerated in the same reaction for the first time.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"1 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142820721","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
Tf2O-Induced Selective 1,3-Transposition/Cyclization of Ynones in DMF
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-14 DOI: 10.1039/d4qo01890g
Huilin Lan, Wenting Liu, Wen Liu, Jiajian Peng, Ying Bai, Xinxin Shao
{"title":"Tf2O-Induced Selective 1,3-Transposition/Cyclization of Ynones in DMF","authors":"Huilin Lan, Wenting Liu, Wen Liu, Jiajian Peng, Ying Bai, Xinxin Shao","doi":"10.1039/d4qo01890g","DOIUrl":"https://doi.org/10.1039/d4qo01890g","url":null,"abstract":"A chemo and regio-selective system for activating C=O and S=O bonds under transition metal-free conditions is described. Thus, a Tf2O-mediated 1,3-transposition of ynones in DMF has been developed, providing a versatile pathway for the downstream synthesis of diverse five- and seven-membered heterocycles. Furthermore, the catalytic migration of carbonyl functionality conjugated to an alkyne unit is investigated. In the presence of sulfoxide, which undergoes a Pummerer reaction, the in-situ generation of highly reactive sulfonium salts enables efficient access to a wide range of sulfur-containing annulated scaffolds. Importantly, 3-SCF2D chromones were obtained in high yields and D-incorporation. This divergent methodology offers a versatile platform for maximizing molecular complexity and diversity.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"10 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142820722","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
Bifuran- and bithiophene-fused 4,6-dihydro-1,2,7-oxadiborepins as building blocks for conjugated copolymers
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-13 DOI: 10.1039/d4qo01964d
Jonas Bachmann, Andreas Drichel, Jonas Klopf, Abhishek Koner, Adam Slabon, Holger Helten
{"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}
引用次数: 0
Palladium-Catalyzed Three-Component Annulation Reaction Involving Multiple C─H Activation
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-13 DOI: 10.1039/d4qo01857e
Shuai Yang, Xiang Zuo, Yanghui Zhang
{"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}
引用次数: 0
Iminonaphthofuranone synthesis via multiple-component cyclization of 2-naphthols using only molecular oxygen
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-13 DOI: 10.1039/d4qo01939c
Jianyu Dong, Shaofeng Wu, Long Liu, Dan Zhou, Min Mo, Ya-Dong Gao, Lebin Su, Shuang-Feng Yin, Yongbo Zhou
{"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}
引用次数: 0
Photoredox trifluoromethylation of isocyanides to access 2-trifluoromethylated quinolines and indoles 异氰酸酯的光氧化三氟甲基化反应生成 2-三氟甲基化的喹啉和吲哚
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-13 DOI: 10.1039/d4qo02105c
Jin Wang, Yaohui Liu, Jinhai Xu, Peiyuan Li, Xiaoxi Xu, Shuo Zhang, Jie Yang, Xianxiu Xu
{"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}
引用次数: 0
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
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