Journal of Organic Chemistry最新文献_第5页

Synthesis of 2-Phosphonylated C3 Spirocyclic Indolines via a Dearomatization–Spirocyclization–Nucleophilic Addition Tandem Approach of Indolyl-ynones with Phosphine Oxides

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-18 DOI: 10.1021/acs.joc.4c02364

Jiongjiong Duan, Yi Cao, Huanping Xie, Yongqi Yu, Heyun Sheng, Weiguang Kong, Ting Li

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Nickel Photoredox/Dual-Catalyzed Transfer Semi-Hydrogenation of Alkynes via Aminoalkyl Nickel Species

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-18 DOI: 10.1021/acs.joc.4c02071

Kento Nakamura, Kokona Odama, Tomoya Fukuta, Yoshihiro Sato

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Palladium-Catalyzed Domino Carboetherification Reactions: Synthesis of Bis-Heterocycles Bearing Isoxazoline and Methyleneindole Motifs

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-18 DOI: 10.1021/acs.joc.4c02679

Feifei Jin, Qing Wu, Shuaijie Wu, Huiwen Dong, Yanru He, Jing Sun, Chao-Guo Yan, Wenbo Li, Lei Wang

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Sustainable Synthesis of Substituted 1,3,5-Triazines by [ONO]-Pincer-Supported Nickel(II) Complexes via an Acceptorless Dehydrogenative Coupling Strategy

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-18 DOI: 10.1021/acs.joc.4c02118

Anandaraj Pennamuthiriyan, Ramesh Rengan, Jan Grzegorz Malecki

{"title":"Sustainable Synthesis of Substituted 1,3,5-Triazines by [ONO]-Pincer-Supported Nickel(II) Complexes via an Acceptorless Dehydrogenative Coupling Strategy","authors":"Anandaraj Pennamuthiriyan, Ramesh Rengan, Jan Grzegorz Malecki","doi":"10.1021/acs.joc.4c02118","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02118","url":null,"abstract":"A facile, cost-effective, and sustainable synthesis of substituted triazines from primary alcohols by newly synthesized nickel pincer-type complexes (1–3) has been described. Herein, we report the synthesis of a set of three well-defined Ni(II) O^N^O pincer-type complexes, structurally characterized by analytical, spectral, and X-ray diffraction techniques. Further, the nickel complexes are explored as efficient catalysts (4 mol %) for the construction of 2,4,6-substituted 1,3,5-triazines from readily available alcohols via an acceptorless dehydrogenative coupling (ADC) strategy. A wide range of substituted triazine derivatives (33 examples) has been synthesized from the coupling of alcohols and benzamidine/guanidine hydrochloride with a maximum isolated yield of 92% under mild conditions, with eco-friendly H2O and H2 gas as the only byproducts. A plausible mechanism has been proposed based on a sequence of control experiments. Interestingly, the short synthesis of the antiulcer drug irsogladine and the large-scale synthesis of 2,4-diphenyl-6-(p-tolyl)-1,3,5-triazine highlight the convenience of the current methodology.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"62 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142849702","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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Copper-Catalyzed Domino Phosphorylation/Cyclization of ortho-Alkynylketones for Accessing Phosphorylated 1H-Isochromenes

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-17 DOI: 10.1021/acs.joc.4c02239

Xiao-Hong Wei, Xuan Liu, Xiao-Hong Wang, Ya-Wen Xue, Xiao-Jun Yang, Shang-Dong Yang

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Palladium-Catalyzed Annulation Reaction of Bay-Iodobiphenyls with Maleimides to Access 9,10-Phenanthrenedicarboximides

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-17 DOI: 10.1021/acs.joc.4c02359

Xin-Yuan Long, Na Huang, Cheng-Rong Cui, Yingbo Shi, Chun Feng, Bi-Qin Wang, Shilin Zhang, Shi-Kai Xiang

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Hydrogen Bond Donor-Catalyzed One-Pot Transformations of 2,2-Disubstituted Epoxides: Synthesis of Functionalized Nitrile-Rich Derivatives 氢键供体催化的 2,2-二取代环氧化物的一锅转化：功能化富腈衍生物的合成

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-17 DOI: 10.1021/acs.joc.4c02111

Sibasish Manna, Koushik Das, Sandipan Halder

{"title":"Hydrogen Bond Donor-Catalyzed One-Pot Transformations of 2,2-Disubstituted Epoxides: Synthesis of Functionalized Nitrile-Rich Derivatives","authors":"Sibasish Manna, Koushik Das, Sandipan Halder","doi":"10.1021/acs.joc.4c02111","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02111","url":null,"abstract":"A practically intriguing catalytic domino methodology has been developed for the synthesis of highly functionalized pyran and ethene-1,1,2-tricarbonitrile derivatives in a single-pot operation. The gem-dicyano olefins and the corresponding epoxide were taken as the reactive partners in the presence of a hydrogen bond donor (HBD)-catalyzed condition. The reaction was found to be highly efficient in terms of the formation of sequential C–C and O–C bonds along with an exceptional CSp2–CSp coupling step through a metal-free organocatalytic pathway. This strategy has been further utilized on ester-substituted epoxides, although the results differ from those with gem-dicyano epoxides. The process remains versatile and effective across a wide range of substrates. This catalytic protocol has been proven to be very generalized with varieties of substrate scope. A low catalyst loading, ambient reaction conditions, and satisfactory yields of all of the products are the vital features of this approach. Moreover, the overall atom-economic outcome along with the synergistic reactivity pattern between the activated epoxide and the malononitrile derivatives is also very significant to address the originality of this process. Spectroscopic analysis is utilized to validate the mechanistic interpretation.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832799","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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Site-Selective O-Arylation of Carbohydrate Derivatives through Nickel–Photoredox Catalysis 通过镍光氧催化实现碳水化合物衍生物的位点选择性 O-芳基化

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-17 DOI: 10.1021/acs.joc.4c02402

Sofia Jdanova, James G. Guthrie, Mark S. Taylor

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TiO2-Catalyzed Direct Diazenylation of Active Methylene Compounds with Diazonium Salts

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-17 DOI: 10.1021/acs.joc.4c02266

Edson Evangelista, Yuri P. V. de Carvalho, Iva S. de Jesus, Maria Eduarda S. Rodrigues, Emelli P. Hayashi, Karine N. de Andrade, Rodolfo G. Fiorot, Luana da S. M. Forezi

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Expanding the Repertoire of Large Scaffolds with Syn and Anti Macrocyclic Metacyclophanes

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-17 DOI: 10.1021/acs.joc.4c02295

Liang-Yu Chen, Udayan Chaudhury, Shengkai Wei, Junqi Li

{"title":"Expanding the Repertoire of Large Scaffolds with Syn and Anti Macrocyclic Metacyclophanes","authors":"Liang-Yu Chen, Udayan Chaudhury, Shengkai Wei, Junqi Li","doi":"10.1021/acs.joc.4c02295","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02295","url":null,"abstract":"Understanding how changes in structure translate to changes in molecular shape is key to catalyst optimization and molecular design in medicinal chemistry and materials. One key contributor to the molecular shape is the relative orientation of substituents on a scaffold. Macrocyclic metacyclophanes display their two arenes in a parallel or antiparallel fashion, resulting in anti or syn conformations that lead to disparate relative orientations of the aryl substituents. This work reports the synthesis of new 14- and 16-membered metacyclophanes and the elucidation of their anti/syn preferences by 1H NMR and computational conformational analysis. Most metacyclophanes studied herein display a strong anti or syn preference and, thus, have well-defined substituent orientations. We propose that anti/syn conformational preferences arise from the minimization of torsional strain along the backbone of the macrocycle, which leads to the prediction that metacyclophanes with remote aryl substituents will adopt the same conformation as their unsubstituted counterparts. Exit vector analysis also reveals that anti-metacyclophanes project their substituents into regions in three-dimensional space that are not accessed by other common large scaffolds, e.g., [2.2]paracyclophanes and ferrocenes. This work also demonstrates how ring size and functional groups, two parameters commonly optimized in macrocycle design, can be used to tune molecular shape.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"81 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841801","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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