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Electrochemical Synthesis of γ-Lactones from the Intermolecular Oxidative Coupling between Malonates and Styrenes
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-16 DOI: 10.1021/acs.joc.5c00228
Antoine Lefevre, Régis Guillot, Cyrille Kouklovsky, Guillaume Vincent
{"title":"Electrochemical Synthesis of γ-Lactones from the Intermolecular Oxidative Coupling between Malonates and Styrenes","authors":"Antoine Lefevre, Régis Guillot, Cyrille Kouklovsky, Guillaume Vincent","doi":"10.1021/acs.joc.5c00228","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00228","url":null,"abstract":"We report a ferrocene-mediated electrochemical intermolecular oxidative annulation between malonates and styrenes that avoids the use of excess oxidants such as Mn(OAc)<sub>3</sub>. The reaction proceeds via presumably the generation of a malonyl radical that adds to the styrene. After further anodic oxidation, the resulting benzylic carbocation is intercepted by one of the esters to deliver the desired γ-lactones.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"51 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143635423","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
Cyclohepta[b]indole Core Construction via the Michael Addition/Friedel–Crafts Condensation Sequence
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-16 DOI: 10.1021/acs.joc.4c03006
Konstantin L. Ivanov, Ekaterina M. Budynina
{"title":"Cyclohepta[b]indole Core Construction via the Michael Addition/Friedel–Crafts Condensation Sequence","authors":"Konstantin L. Ivanov, Ekaterina M. Budynina","doi":"10.1021/acs.joc.4c03006","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03006","url":null,"abstract":"An approach to cyclohepta[<i>b</i>]indoles <i>via</i> the formal (4 + 3) annulation of readily synthesized 2-indolyl-derived 1,3-dicarbonyl compounds to acrolein and enones was developed. The process is initiated by catalytic Michael addition, wherein the adduct was generated <i>in situ</i>. The subsequent addition of a Bro̷nsted acid catalyst triggers a cascade process that includes intramolecular Friedel–Crafts hydroxylalkylation followed by dehydration. The cascade reaction is relatively undemanding since even degrading chloroform is able to initiate it. The obtained tetrahydrocyclohepta[<i>b</i>]indoles were prone toward easy dimerization, underscoring the high reactivity of the double bond in the seven-membered ring.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"24 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143635418","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
Electrochemical Synthesis of γ-Lactones from the Intermolecular Oxidative Coupling between Malonates and Styrenes
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-16 DOI: 10.1021/acs.joc.5c0022810.1021/acs.joc.5c00228
Antoine Lefevre, Régis Guillot, Cyrille Kouklovsky and Guillaume Vincent*, 
{"title":"Electrochemical Synthesis of γ-Lactones from the Intermolecular Oxidative Coupling between Malonates and Styrenes","authors":"Antoine Lefevre,&nbsp;Régis Guillot,&nbsp;Cyrille Kouklovsky and Guillaume Vincent*,&nbsp;","doi":"10.1021/acs.joc.5c0022810.1021/acs.joc.5c00228","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00228https://doi.org/10.1021/acs.joc.5c00228","url":null,"abstract":"<p >We report a ferrocene-mediated electrochemical intermolecular oxidative annulation between malonates and styrenes that avoids the use of excess oxidants such as Mn(OAc)<sub>3</sub>. The reaction proceeds via presumably the generation of a malonyl radical that adds to the styrene. After further anodic oxidation, the resulting benzylic carbocation is intercepted by one of the esters to deliver the desired γ-lactones.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 12","pages":"4450–4457 4450–4457"},"PeriodicalIF":3.3,"publicationDate":"2025-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143713926","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 Polycyclic Heteroarenes via Rh(III)-Catalyzed Twofold C-H Activation of 3-Aryl-2H-benzo[b][1,4]oxazines and Annulation with α-Diazo-β-ketoesters 通过 Rh(III)-Catalyzed Twofold C-H Activation of 3-Aryl-2H-benzo[b][1,4]oxazines and Annulation with α-Diazo-β-ketoesters 合成多环杂烯烃
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-14 DOI: 10.1021/acs.joc.5c00036
Yiyue Li, Song Li, Haokang Du, Youwu Hao, Yi-Nan Cheng, Xiangyang Liu, Xifa Yang
{"title":"Synthesis of Polycyclic Heteroarenes via Rh(III)-Catalyzed Twofold C-H Activation of 3-Aryl-2H-benzo[b][1,4]oxazines and Annulation with α-Diazo-β-ketoesters","authors":"Yiyue Li, Song Li, Haokang Du, Youwu Hao, Yi-Nan Cheng, Xiangyang Liu, Xifa Yang","doi":"10.1021/acs.joc.5c00036","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00036","url":null,"abstract":"An efficient Rh(III)-catalyzed annulation between 3-aryl-2<i>H</i>-benzo[<i>b</i>][1,4]oxazines and α-diazo-β-ketoesters was developed, affording a series of polycyclic heteroarenes in moderate to excellent yields with good functional group compatibility. The procedure featured high efficiency, redox neutrality, twofold <i>ortho</i>-C-H activation, and dual [4 + 2] annulation. Moreover, several important intermediates and products have been isolated as powerful evidence for the proposed reaction mechanism.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"33 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143627705","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 Polycyclic Heteroarenes via Rh(III)-Catalyzed Twofold C-H Activation of 3-Aryl-2H-benzo[b][1,4]oxazines and Annulation with α-Diazo-β-ketoesters
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-14 DOI: 10.1021/acs.joc.5c0003610.1021/acs.joc.5c00036
Yiyue Li, Song Li, Haokang Du, Youwu Hao, Yi-Nan Cheng, Xiangyang Liu* and Xifa Yang*, 
{"title":"Synthesis of Polycyclic Heteroarenes via Rh(III)-Catalyzed Twofold C-H Activation of 3-Aryl-2H-benzo[b][1,4]oxazines and Annulation with α-Diazo-β-ketoesters","authors":"Yiyue Li,&nbsp;Song Li,&nbsp;Haokang Du,&nbsp;Youwu Hao,&nbsp;Yi-Nan Cheng,&nbsp;Xiangyang Liu* and Xifa Yang*,&nbsp;","doi":"10.1021/acs.joc.5c0003610.1021/acs.joc.5c00036","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00036https://doi.org/10.1021/acs.joc.5c00036","url":null,"abstract":"<p >An efficient Rh(III)-catalyzed annulation between 3-aryl-2<i>H</i>-benzo[<i>b</i>][1,4]oxazines and α-diazo-β-ketoesters was developed, affording a series of polycyclic heteroarenes in moderate to excellent yields with good functional group compatibility. The procedure featured high efficiency, redox neutrality, twofold <i>ortho</i>-C-H activation, and dual [4 + 2] annulation. Moreover, several important intermediates and products have been isolated as powerful evidence for the proposed reaction mechanism.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 12","pages":"4337–4346 4337–4346"},"PeriodicalIF":3.3,"publicationDate":"2025-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143713858","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
Tether-Directed Electrosynthesis of Bicyclic [60]Fullerene Derivatives Fused with 5-Membered Azacycle and 13-Membered Carbocycle
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-14 DOI: 10.1021/acs.joc.5c0005210.1021/acs.joc.5c00052
Zheng-Chun Yin*, Qian-Wen Zhang, Wen-Rui Liu, Chuang Niu, Muqing Chen and Guan-Wu Wang*, 
{"title":"Tether-Directed Electrosynthesis of Bicyclic [60]Fullerene Derivatives Fused with 5-Membered Azacycle and 13-Membered Carbocycle","authors":"Zheng-Chun Yin*,&nbsp;Qian-Wen Zhang,&nbsp;Wen-Rui Liu,&nbsp;Chuang Niu,&nbsp;Muqing Chen and Guan-Wu Wang*,&nbsp;","doi":"10.1021/acs.joc.5c0005210.1021/acs.joc.5c00052","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00052https://doi.org/10.1021/acs.joc.5c00052","url":null,"abstract":"<p >Tether-directed electrosynthesis of [60]fullerene derivatives fused with 5-membered azacycle and 13-membered carbocycle, that is, bicyclic 1,4,9,12- and 1,2,4,15-adducts, has been achieved unexpectedly for the first time. The novel bicyclic [60]fullerene derivatives are obtained by the electrochemical reduction of [60]fullerene-fused indolines or lactams and subsequent regioselective cyclization with 2,2″-bis(bromomethyl)-1,1′:3′,1″-terphenyl. The product structures have been characterized by spectroscopic data and single-crystal X-ray analysis.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 12","pages":"4347–4356 4347–4356"},"PeriodicalIF":3.3,"publicationDate":"2025-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143714106","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
Bis-zirconocenes Generated from Weinreb 2-Allylaminoacetamides as Key Intermediates for a Diastereoselective Approach to 2- and 6-Substituted-3-Aminopiperidines
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-14 DOI: 10.1021/acs.joc.4c02399
Mohamed El Gharbi, Emilie Bianchi, Aurélien Coelho, Christelle Kowandy, Jean-Bernard Behr, Jean-Luc Vasse
{"title":"Bis-zirconocenes Generated from Weinreb 2-Allylaminoacetamides as Key Intermediates for a Diastereoselective Approach to 2- and 6-Substituted-3-Aminopiperidines","authors":"Mohamed El Gharbi, Emilie Bianchi, Aurélien Coelho, Christelle Kowandy, Jean-Bernard Behr, Jean-Luc Vasse","doi":"10.1021/acs.joc.4c02399","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02399","url":null,"abstract":"The synthesis of 2- and 6-substituted-3-aminopiperidines from Weinreb amides containing an allylamino fragment is reported. Involving the simultaneous hydrozirconation of the C═C and the C═O bonds, the cyclization was promoted by the BF<sub>3</sub>-mediated generation of an iminium. Proven to be highly diastereoselective, the sequence can be applied to diversely substituted unsaturated Weinreb amides and valorized through the preparation of bicyclic heterocycles.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"183 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143627708","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
Bis-zirconocenes Generated from Weinreb 2-Allylaminoacetamides as Key Intermediates for a Diastereoselective Approach to 2- and 6-Substituted-3-Aminopiperidines
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-14 DOI: 10.1021/acs.joc.4c0239910.1021/acs.joc.4c02399
Mohamed El Gharbi, Emilie Bianchi, Aurélien Coelho, Christelle Kowandy, Jean-Bernard Behr and Jean-Luc Vasse*, 
{"title":"Bis-zirconocenes Generated from Weinreb 2-Allylaminoacetamides as Key Intermediates for a Diastereoselective Approach to 2- and 6-Substituted-3-Aminopiperidines","authors":"Mohamed El Gharbi,&nbsp;Emilie Bianchi,&nbsp;Aurélien Coelho,&nbsp;Christelle Kowandy,&nbsp;Jean-Bernard Behr and Jean-Luc Vasse*,&nbsp;","doi":"10.1021/acs.joc.4c0239910.1021/acs.joc.4c02399","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02399https://doi.org/10.1021/acs.joc.4c02399","url":null,"abstract":"<p >The synthesis of 2- and 6-substituted-3-aminopiperidines from Weinreb amides containing an allylamino fragment is reported. Involving the simultaneous hydrozirconation of the C═C and the C═O bonds, the cyclization was promoted by the BF<sub>3</sub>-mediated generation of an iminium. Proven to be highly diastereoselective, the sequence can be applied to diversely substituted unsaturated Weinreb amides and valorized through the preparation of bicyclic heterocycles.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 12","pages":"4134–4139 4134–4139"},"PeriodicalIF":3.3,"publicationDate":"2025-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143713856","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
Tether-Directed Electrosynthesis of Bicyclic [60]Fullerene Derivatives Fused with 5-Membered Azacycle and 13-Membered Carbocycle
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-14 DOI: 10.1021/acs.joc.5c00052
Zheng-Chun Yin, Qian-Wen Zhang, Wen-Rui Liu, Chuang Niu, Muqing Chen, Guan-Wu Wang
{"title":"Tether-Directed Electrosynthesis of Bicyclic [60]Fullerene Derivatives Fused with 5-Membered Azacycle and 13-Membered Carbocycle","authors":"Zheng-Chun Yin, Qian-Wen Zhang, Wen-Rui Liu, Chuang Niu, Muqing Chen, Guan-Wu Wang","doi":"10.1021/acs.joc.5c00052","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00052","url":null,"abstract":"Tether-directed electrosynthesis of [60]fullerene derivatives fused with 5-membered azacycle and 13-membered carbocycle, that is, bicyclic 1,4,9,12- and 1,2,4,15-adducts, has been achieved unexpectedly for the first time. The novel bicyclic [60]fullerene derivatives are obtained by the electrochemical reduction of [60]fullerene-fused indolines or lactams and subsequent regioselective cyclization with 2,2″-bis(bromomethyl)-1,1′:3′,1″-terphenyl. The product structures have been characterized by spectroscopic data and single-crystal X-ray analysis.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"204 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143627772","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
A Precise Synthetic Toolbox: H-Bond-Assisted Quadruple Reactivity of o-Dimethylaminoaryloximes
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-13 DOI: 10.1021/acs.joc.5c00207
Semyon V. Tsybulin, Stepan A. Meshalkin, Daria I. Tonkoglazova, Victor G. Bardakov, Alexander F. Pozharskii, Alexander S. Antonov
{"title":"A Precise Synthetic Toolbox: H-Bond-Assisted Quadruple Reactivity of o-Dimethylaminoaryloximes","authors":"Semyon V. Tsybulin, Stepan A. Meshalkin, Daria I. Tonkoglazova, Victor G. Bardakov, Alexander F. Pozharskii, Alexander S. Antonov","doi":"10.1021/acs.joc.5c00207","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00207","url":null,"abstract":"Non-covalent interactions are a highly promising tool for the development of transition-metal-free chemospecific synthetic transformations. Here, we demonstrate the implementation of non-covalent interactions as a simple, precise, and flexible synthetic toolbox, allowing the controlled transformation of <i>o</i>-dimethylaminoaryloximes into nitriles and hard-to-reach nitrogen heterocycles under mild conditions. This diverse reactivity is activated via hydrogen bonding and facilitated via the “buttressing effect” of the substituents next to the NMe<sub>2</sub> group. All transformations require only simple and easily available acids and solvents, which generally provide precise control over the direction of the reaction, allowing the selective synthesis of nitriles, fused pyrazoles, isoxazoles, and pyrroles.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"8 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143618801","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
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