Journal of Organic Chemistry最新文献_第7页

Nucleophile-Controlled Regiodivergent Domino Reactions of Enetriones with γ-Bromocrotonates: Access to 1,3-Dienic Esters and Tetrasubstituted Pyrans 亲核控制的烯三酮与γ-溴代丙酮酸酯的区域发散多米诺反应：1,3-二烯酯和四取代吡喃的获得

IF 3.3 2区化学

Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1021/acs.joc.4c0315910.1021/acs.joc.4c03159

Dan Xiong, Sen Zhang, Zhiyue Li, Hui Yao*, Linxuan Li, Nianyu Huang* and Nengzhong Wang*,

{"title":"Nucleophile-Controlled Regiodivergent Domino Reactions of Enetriones with γ-Bromocrotonates: Access to 1,3-Dienic Esters and Tetrasubstituted Pyrans","authors":"Dan Xiong, Sen Zhang, Zhiyue Li, Hui Yao*, Linxuan Li, Nianyu Huang* and Nengzhong Wang*, ","doi":"10.1021/acs.joc.4c0315910.1021/acs.joc.4c03159","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03159https://doi.org/10.1021/acs.joc.4c03159","url":null,"abstract":"Herein, we developed an efficient nucleophile-controlled regiodivergent domino reaction between enetriones and γ-bromocrotonates. This method allowed for the rapid synthesis of a range of 1,3-dienic esters and tetrasubstituted pyrans under metal-free conditions. In the presence of pyridine, a SN2 substitution/Michael addition/elimination sequence formed 1,3-dienic esters in satisfactory yields with high E-stereoselectivities. Alternatively, a SN2 substitution/Michael addition/cyclization/cyclopropanation/cyclopropane ring-opening process forged tetrasubstituted pyrans in good yields with the help of Et3N. It is interesting to note that the site-selective reactions of γ-bromocrotonates at the α- or γ-position were readily realized by modulating pyridine and Et3N. Furthermore, the simple pyridine and Et3N act as both nucleophiles in SN2 substitution reactions and Lewis bases in deprotonation processes.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"5838–5844 5838–5844"},"PeriodicalIF":3.3,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894059","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

N-Heterocyclic Carbene-Catalyzed [4 + 2] Annulation of Enolizable Thioesters for the Synthesis of 2-Pyrones n -杂环碳催化[4 + 2]环化可烯化硫酯合成2-吡咯酮

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1021/acs.joc.5c00428

Jinfeng Zhang, Chen Zhu, Xu Cao, Hui Jin, Lixin Zhang

引用次数: 0

Cross-Dimerization Giving Silyl-Substituted Conjugated Hexatrienes: An Approach to 1,6-Diarylhexa-1,3,5-trienes 交叉二聚化生成硅基取代共轭六烯：1,6-二烷基六烯-1,3,5-三烯的方法

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1021/acs.joc.5c00218

Fuma Sakamoto, Eri Arata, Ryo Saito, Sayori Kiyota, Nobuyuki Komine, Masafumi Hirano

{"title":"Cross-Dimerization Giving Silyl-Substituted Conjugated Hexatrienes: An Approach to 1,6-Diarylhexa-1,3,5-trienes","authors":"Fuma Sakamoto, Eri Arata, Ryo Saito, Sayori Kiyota, Nobuyuki Komine, Masafumi Hirano","doi":"10.1021/acs.joc.5c00218","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00218","url":null,"abstract":"A new approach to 1,6-diarylhexa-1,3,5-trienes (DAHs) has been achieved. Cross-dimerization of 1-aryl-2-silylethyne (1) with benzyl((E)-buta-1,3-dien-1-yl)dimethylsilane (2c) catalyzed by [Ru(η6-naphthalene)(η4-1,5-cycloocatdiene)] produces (1E,3E)-(6-aryl-5-silylhexa-1,3,5-trien-1-yl)benzyl(dimethyl)silane (3), where the dominant stereochemistry at the 5-position in 3 is the E-form. Subsequent Hiyama cross-coupling of 3 with aryl iodide catalyzed by [Pd2(dibenzylideneacetone)3]·C6H6 in the presence of TBAF·3H2O gives a series of (1E,3E,5E)-1,6-diarylhexa-1,3,5-trienes (DAH), showing that the C(5)═C(6) double bond rotates in the event of protodesilylation. The controlled experiments suggest that the Hiyama cross-coupling of the terminal silyl group in 3 takes place first, and then protodesilylation of the internal silyl group occurs to give (1E,3E,5E)-DAHs. An X-ray structure analysis reveals the molecular structure of (1E,3E,5E)-1-(4-acetylphenyl)-6-phenylhexa-1,3,5-triene. The photochemical study of some new DAHs has been conducted, showing bright fluorescence upon irradiation with a large Stokes shift (∼4026 cm–1) by π–π* transition according to TD-DFT calculations.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"7 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143867124","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

Nucleophile-Controlled Regiodivergent Domino Reactions of Enetriones with γ-Bromocrotonates: Access to 1,3-Dienic Esters and Tetrasubstituted Pyrans 亲核控制的烯三酮与γ-溴代丙酮酸酯的区域发散多米诺反应：1,3-二烯酯和四取代吡喃的获得

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1021/acs.joc.4c03159

Dan Xiong, Sen Zhang, Zhiyue Li, Hui Yao, Linxuan Li, Nianyu Huang, Nengzhong Wang

引用次数: 0

Synthesis of 3-Amino-β-lactams through Selective Imination of 3-Oxo-β-lactams 选择性模拟3-氧-β-内酰胺合成3-氨基-β-内酰胺

IF 3.3 2区化学

Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1021/acs.joc.5c0020510.1021/acs.joc.5c00205

Sari Deketelaere, Emma Vandenheede, Nicola Piens, Lore Cools, Lieselotte Crul, Lotte Demeurisse, Karen Mollet, Christian V. Stevens and Matthias D’hooghe*,

{"title":"Synthesis of 3-Amino-β-lactams through Selective Imination of 3-Oxo-β-lactams","authors":"Sari Deketelaere, Emma Vandenheede, Nicola Piens, Lore Cools, Lieselotte Crul, Lotte Demeurisse, Karen Mollet, Christian V. Stevens and Matthias D’hooghe*, ","doi":"10.1021/acs.joc.5c0020510.1021/acs.joc.5c00205","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00205https://doi.org/10.1021/acs.joc.5c00205","url":null,"abstract":"3-Oxo-β-lactams are known to deliver different types of reaction products upon treatment with primary amines, predominantly governed by the nature of the C4 substituent. In this work, a C4 substituent-independent protocol for the conversion of 3-oxo-β-lactams to the corresponding 3-imino-β-lactams was developed. By using primary amine hydrochloric acid salts in combination with 2,4,6-collidine, or free primary amines in combination with acetic acid, the undesired ring opening of 4-aryl- and (S)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)azetidine-2,3-diones toward ethanediamides and α-aminoamides, respectively, is avoided, enabling the smooth transformation of any 3-oxo-β-lactam into its imine counterpart. As demonstrated by the ensuing synthesis of 3-alkylamino-β-lactams, 3-imino-β-lactams serve as building blocks for the construction of functionalized 3-amino-β-lactams, with the latter being key motifs in drug discovery.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"5903–5916 5903–5916"},"PeriodicalIF":3.3,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894064","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

One-Pot Synthesis of Tricyclic Benzoxazines and Benzoxazepine by Heterogeneous Biochemo Multienzyme Cascade Reaction. 非均相生化多酶级联反应一锅法合成三环苯并恶嗪和苯并恶西平。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1021/acs.joc.4c02868

Eliana Capecchi,Elisabetta Tomaino,Bruno M Bizzarri,Raffaele Saladino

引用次数: 0

Scalable Multistep One-Pot Synthesis of Natural and Modified Nucleoside Triphosphates 天然和修饰三磷酸核苷的多步一锅合成

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1021/acs.joc.5c00268

Sergei Negria, Yinglong Jia, Noah A. Setterholm, Bhawna Barpuzary, John C. Chaput

引用次数: 0

Synthesis of Thienoacenes via Cascade Copper-Catalyzed C–S Coupling and Thienannulation Reactions and Their Thermoelectric Properties 级联铜催化C-S偶联和硫烯环化反应合成噻吩烯及其热电性能

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1021/acs.joc.4c03182

Jiaxuan Dong, Yifan Lv, Yiyang Li, Kexin Xu, Xinrui Cui, Cun-Yue Guo, Baolin Li

{"title":"Synthesis of Thienoacenes via Cascade Copper-Catalyzed C–S Coupling and Thienannulation Reactions and Their Thermoelectric Properties","authors":"Jiaxuan Dong, Yifan Lv, Yiyang Li, Kexin Xu, Xinrui Cui, Cun-Yue Guo, Baolin Li","doi":"10.1021/acs.joc.4c03182","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03182","url":null,"abstract":"Thienoacenes are a prominent class of fused-ring conjugated organic compounds and have attracted considerable attention due to their high coplanarity, good stability, high charge-carrier mobility, etc. However, most current synthetic methods toward thienoacenes require costly starting materials and reagents, as well as a lengthy synthetic procedure with low overall yields. Herein, a nonprecious copper-catalyzed system without additional ligands was developed to facilitate C–S coupling and 5-endo-dig thienannulation reaction, leading to the synthesis of a range of thienoacenes including dithieno[3,2-b:2′,3′-d]thiophenes (DTTs) and thieno[2′,3′:4,5]thieno[3,2-b]thiophene[2,3-d]thiophene (TTAs) with yields of up to 90% (for single-sided thienannulation reactions) and 65% (for double-sided thienannulation reactions). In addition, three π-extended DTTs were studied as potential thermoelectric materials, and their composites with single-walled carbon nanotubes (SWCNTs) exhibited high thermoelectric performance with the power factor up to 399.01 ± 16.26 μW m–1 K–2 at room temperature, which is the highest reported for thermoelectric composites comprising small-molecule thiophene derivatives and SWCNTs, signifying a step forward in the development of high-performance thermoelectric composites based on thiophene derivatives.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143867123","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

Synthesis of Thienoacenes via Cascade Copper-Catalyzed C–S Coupling and Thienannulation Reactions and Their Thermoelectric Properties 级联铜催化C-S偶联和硫烯环化反应合成噻吩烯及其热电性能

IF 3.3 2区化学

Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1021/acs.joc.4c0318210.1021/acs.joc.4c03182

Jiaxuan Dong, Yifan Lv, Yiyang Li, Kexin Xu, Xinrui Cui, Cun-Yue Guo* and Baolin Li*,

{"title":"Synthesis of Thienoacenes via Cascade Copper-Catalyzed C–S Coupling and Thienannulation Reactions and Their Thermoelectric Properties","authors":"Jiaxuan Dong, Yifan Lv, Yiyang Li, Kexin Xu, Xinrui Cui, Cun-Yue Guo* and Baolin Li*, ","doi":"10.1021/acs.joc.4c0318210.1021/acs.joc.4c03182","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03182https://doi.org/10.1021/acs.joc.4c03182","url":null,"abstract":"Thienoacenes are a prominent class of fused-ring conjugated organic compounds and have attracted considerable attention due to their high coplanarity, good stability, high charge-carrier mobility, etc. However, most current synthetic methods toward thienoacenes require costly starting materials and reagents, as well as a lengthy synthetic procedure with low overall yields. Herein, a nonprecious copper-catalyzed system without additional ligands was developed to facilitate C–S coupling and 5-endo-dig thienannulation reaction, leading to the synthesis of a range of thienoacenes including dithieno[3,2-b:2′,3′-d]thiophenes (DTTs) and thieno[2′,3′:4,5]thieno[3,2-b]thiophene[2,3-d]thiophene (TTAs) with yields of up to 90% (for single-sided thienannulation reactions) and 65% (for double-sided thienannulation reactions). In addition, three π-extended DTTs were studied as potential thermoelectric materials, and their composites with single-walled carbon nanotubes (SWCNTs) exhibited high thermoelectric performance with the power factor up to 399.01 ± 16.26 μW m–1 K–2 at room temperature, which is the highest reported for thermoelectric composites comprising small-molecule thiophene derivatives and SWCNTs, signifying a step forward in the development of high-performance thermoelectric composites based on thiophene derivatives.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"5845–5855 5845–5855"},"PeriodicalIF":3.3,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894060","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

N-Heterocyclic Carbene-Catalyzed [4 + 2] Annulation of Enolizable Thioesters for the Synthesis of 2-Pyrones n -杂环碳催化[4 + 2]环化可烯化硫酯合成2-吡咯酮

IF 3.3 2区化学

Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1021/acs.joc.5c0042810.1021/acs.joc.5c00428

Jinfeng Zhang, Chen Zhu, Xu Cao, Hui Jin* and Lixin Zhang*,

引用次数: 0