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Thermal Cα–C6 Cyclization of Enediynes 烯二炔的c - α - c6热环化
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1021/acs.joc.4c0312410.1021/acs.joc.4c03124
Haonan Cheng, Wenbo Wang, Yun Zeng, Houjun Zhang, Xiaohua Huang, Fangxu Pu, Xiaofan Zhang, Aiguo Hu* and Yun Ding*, 
{"title":"Thermal Cα–C6 Cyclization of Enediynes","authors":"Haonan Cheng,&nbsp;Wenbo Wang,&nbsp;Yun Zeng,&nbsp;Houjun Zhang,&nbsp;Xiaohua Huang,&nbsp;Fangxu Pu,&nbsp;Xiaofan Zhang,&nbsp;Aiguo Hu* and Yun Ding*,&nbsp;","doi":"10.1021/acs.joc.4c0312410.1021/acs.joc.4c03124","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03124https://doi.org/10.1021/acs.joc.4c03124","url":null,"abstract":"<p >Canonical thermal cycloaromatizations (Bergman, C<sup>1</sup>–C<sup>6</sup>; Myers-Saito, C<sup>2</sup>–C<sup>7</sup>; Schmittel, C<sup>2</sup>–C<sup>6</sup>; Schreiner-Pascal, C<sup>1</sup>–C<sup>5</sup>) are limited to the formation of five- or six-membered rings, while the formation of larger rings from enediyne (or enyne-allenes) has no precedent experimental exploration. Herein, we present a novel thermal cyclization of enediyne, leading to the formation of a stable seven-membered cyclization product. The structure of this product was elucidated by using NMR and single-crystal X-ray diffraction techniques. The presence of a maleic hydrazide moiety is postulated to facilitate the proton transfer, resulting in the rearrangement of enediyne to enyne-allene, culminating in ring closure through C<sup>α</sup>–C<sup>6</sup> cyclization. The reaction mechanism was further explored by using density functional theory (DFT), revealing a low activation barrier for the C<sup>α</sup>–C<sup>6</sup> cyclization at 19.6 kcal/mol. The newly formed seven-membered ring exhibits strong Möbius aromaticity, as confirmed by calculations of the nucleus-independent chemical shift (NICS) and anisotropy of the induced current density (ACID). In the subsequent reaction, the fusion of the oxazolidin-2-one ring and the elimination of the isobutene molecule release a significant amount of energy, further driving the formation of the final product.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"5828–5837 5828–5837"},"PeriodicalIF":3.3,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894264","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
Straightforward Access to 4-Sulfenylated Isocoumarins via Sulfoxides/MOMCl-Enabled Regioselective Cleavage and Reconfiguration of C–S Bonds 通过亚砜/ momcl激活C-S键的区域选择性切割和重配置直接获得4-磺化异香豆素
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1021/acs.joc.5c0028710.1021/acs.joc.5c00287
Linlin Xing, Shiyan Cao, Hezhuang Feng, Haixia Zheng, Haoyuan Fan, Kai Wang, Yongjun Zheng, Yong Zhang and Yunfei Du*, 
{"title":"Straightforward Access to 4-Sulfenylated Isocoumarins via Sulfoxides/MOMCl-Enabled Regioselective Cleavage and Reconfiguration of C–S Bonds","authors":"Linlin Xing,&nbsp;Shiyan Cao,&nbsp;Hezhuang Feng,&nbsp;Haixia Zheng,&nbsp;Haoyuan Fan,&nbsp;Kai Wang,&nbsp;Yongjun Zheng,&nbsp;Yong Zhang and Yunfei Du*,&nbsp;","doi":"10.1021/acs.joc.5c0028710.1021/acs.joc.5c00287","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00287https://doi.org/10.1021/acs.joc.5c00287","url":null,"abstract":"<p >The combination of sulfoxides with MOMCl has been found for the first time to mediate electrophilic cyclization and install a variety of sulfenyl groups onto isocoumarin skeletons via regioselective cleavage and reconfiguration of C–S bonds. Notably, MOMCl, a mild and readily available alkyl chloride, was indispensable and played a significant role as an activator under neutral conditions in this transformation, thus expanding the scope of acid-labile substrates.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"5957–5965 5957–5965"},"PeriodicalIF":3.3,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894271","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
Strain-Releasing Hydrogenation of Donor–Acceptor Cyclopropanes and Cyclobutanes via Electrochemical Site Selective Carbonyl Reduction 电化学位点选择性羰基还原对施主-受体环丙烷和环丁烷的释放氢化反应
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-21 DOI: 10.1021/acs.joc.5c00180
Nakshatra Banerjee, Rakesh Kumar, Biswadeep Manna, Prabal Banerjee
{"title":"Strain-Releasing Hydrogenation of Donor–Acceptor Cyclopropanes and Cyclobutanes via Electrochemical Site Selective Carbonyl Reduction","authors":"Nakshatra Banerjee, Rakesh Kumar, Biswadeep Manna, Prabal Banerjee","doi":"10.1021/acs.joc.5c00180","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00180","url":null,"abstract":"An acid or hydrogen gas-free electrochemical protocol is established for the hydrogenation of strained rings (cyclopropane and cyclobutane) at room temperature and atmospheric pressure. The mechanistic study revealed that the reaction was initiated via the reduction of the carbonyl group. The methodology is highly specific toward strained rings such as cyclopropane and cyclobutane, which exhibit broad functional group tolerance.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"219 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143853591","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
Strain-Releasing Hydrogenation of Donor–Acceptor Cyclopropanes and Cyclobutanes via Electrochemical Site Selective Carbonyl Reduction 电化学位点选择性羰基还原对施主-受体环丙烷和环丁烷的释放氢化反应
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-21 DOI: 10.1021/acs.joc.5c0018010.1021/acs.joc.5c00180
Nakshatra Banerjee, Rakesh Kumar, Biswadeep Manna and Prabal Banerjee*, 
{"title":"Strain-Releasing Hydrogenation of Donor–Acceptor Cyclopropanes and Cyclobutanes via Electrochemical Site Selective Carbonyl Reduction","authors":"Nakshatra Banerjee,&nbsp;Rakesh Kumar,&nbsp;Biswadeep Manna and Prabal Banerjee*,&nbsp;","doi":"10.1021/acs.joc.5c0018010.1021/acs.joc.5c00180","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00180https://doi.org/10.1021/acs.joc.5c00180","url":null,"abstract":"<p >An acid or hydrogen gas-free electrochemical protocol is established for the hydrogenation of strained rings (cyclopropane and cyclobutane) at room temperature and atmospheric pressure. The mechanistic study revealed that the reaction was initiated via the reduction of the carbonyl group. The methodology is highly specific toward strained rings such as cyclopropane and cyclobutane, which exhibit broad functional group tolerance.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"5890–5902 5890–5902"},"PeriodicalIF":3.3,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894164","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
Intra-/Intermolecular 1,2-Diamination of Alkenyl Oximes with O-Benzoylhydroxylamines Enabled by Copper Catalysis 烯基肟与邻苯甲酰羟胺的分子内/分子间1,2-二化反应
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-21 DOI: 10.1021/acs.joc.5c0027110.1021/acs.joc.5c00271
Jiangfei Chen, Qi Xue, Shenyu Ren, Yi-Lin Liu*, Yang Li* and Jin-Heng Li*, 
{"title":"Intra-/Intermolecular 1,2-Diamination of Alkenyl Oximes with O-Benzoylhydroxylamines Enabled by Copper Catalysis","authors":"Jiangfei Chen,&nbsp;Qi Xue,&nbsp;Shenyu Ren,&nbsp;Yi-Lin Liu*,&nbsp;Yang Li* and Jin-Heng Li*,&nbsp;","doi":"10.1021/acs.joc.5c0027110.1021/acs.joc.5c00271","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00271https://doi.org/10.1021/acs.joc.5c00271","url":null,"abstract":"<p >We here describe a versatile, convenient, and efficient approach to synthesize cyclic nitrone compounds by diamination of alkene, which was catalyzed by simple copper salts under basic conditions with good chemoselectivity. The method utilized γ,δ-unsaturated ketoximes with <i>O</i>-benzoylhydroxylamines as an electrophilic nitrogen source to realize intra-/intermolecular 5-<i>exo</i>-trig cyclization of internal alkenes of unsaturated ketoximes without external oxidants required, and a series of substitution patterns, both donor and withdrawing substituted moieties, are well-tolerated, leading to target products in moderate to good yields.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"5949–5956 5949–5956"},"PeriodicalIF":3.3,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894219","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
Intra-/Intermolecular 1,2-Diamination of Alkenyl Oximes with O-Benzoylhydroxylamines Enabled by Copper Catalysis 铜催化烯基肟与 O-苯甲酰基羟胺的分子内/分子间 1,2-二胺化反应
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-21 DOI: 10.1021/acs.joc.5c00271
Jiangfei Chen, Qi Xue, Shenyu Ren, Yi-Lin Liu, Yang Li, Jin-Heng Li
{"title":"Intra-/Intermolecular 1,2-Diamination of Alkenyl Oximes with O-Benzoylhydroxylamines Enabled by Copper Catalysis","authors":"Jiangfei Chen, Qi Xue, Shenyu Ren, Yi-Lin Liu, Yang Li, Jin-Heng Li","doi":"10.1021/acs.joc.5c00271","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00271","url":null,"abstract":"We here describe a versatile, convenient, and efficient approach to synthesize cyclic nitrone compounds by diamination of alkene, which was catalyzed by simple copper salts under basic conditions with good chemoselectivity. The method utilized γ,δ-unsaturated ketoximes with <i>O</i>-benzoylhydroxylamines as an electrophilic nitrogen source to realize intra-/intermolecular 5-<i>exo</i>-trig cyclization of internal alkenes of unsaturated ketoximes without external oxidants required, and a series of substitution patterns, both donor and withdrawing substituted moieties, are well-tolerated, leading to target products in moderate to good yields.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"64 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143858119","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
Substrate- and Reagent-Controlled Dimerization of Vinyl para-Quinone Methides 底物和试剂控制的乙烯基对醌二聚化反应
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-21 DOI: 10.1021/acs.joc.5c0012310.1021/acs.joc.5c00123
Ryan G. Baker, Kyle D. Reichl, Michael J. Smith, Michael Ricca, Margaret A. Mickelberg and John A. Porco Jr.*, 
{"title":"Substrate- and Reagent-Controlled Dimerization of Vinyl para-Quinone Methides","authors":"Ryan G. Baker,&nbsp;Kyle D. Reichl,&nbsp;Michael J. Smith,&nbsp;Michael Ricca,&nbsp;Margaret A. Mickelberg and John A. Porco Jr.*,&nbsp;","doi":"10.1021/acs.joc.5c0012310.1021/acs.joc.5c00123","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00123https://doi.org/10.1021/acs.joc.5c00123","url":null,"abstract":"<p >Substrate and reagent-controlled dimerization of vinyl <i>para</i>-quinone methides (VPQMs) is reported. When subjected to Brønsted acidic conditions, VPQM dimerization occurs via a formal 1,8-addition to provide griffipavixanthone (GPX)-type congeners. Under optimized Lewis acidic conditions, a change in regioselectivity affords limonene-containing dimers by a 1,6-addition/cyclization process. This divergent reactivity has been explored on several substrates of differing complexity, providing access to analogues of the natural product griffipavixanthone (GPX) as well as a range of novel, substituted limonene dimers.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"5871–5889 5871–5889"},"PeriodicalIF":3.3,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894151","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 Cascade Reactions of 1,2,3-Benzotriazinones with Alkynes to Assemble 3,4-Dihydroisoquinolin-1(2H)-ones 1,2,3-苯并三嗪酮与炔的电化学级联反应组装3,4-二氢异喹啉-1(2H)-酮
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-21 DOI: 10.1021/acs.joc.5c0002210.1021/acs.joc.5c00022
Sanfei Nian*, Xudong Wu, Anwu Chen, Zhiming Lei, Qiuyue Song, Quan Huang, Min Liu, Shengming Lu, Jinkang Chen* and Daijing Wei, 
{"title":"Electrochemical Cascade Reactions of 1,2,3-Benzotriazinones with Alkynes to Assemble 3,4-Dihydroisoquinolin-1(2H)-ones","authors":"Sanfei Nian*,&nbsp;Xudong Wu,&nbsp;Anwu Chen,&nbsp;Zhiming Lei,&nbsp;Qiuyue Song,&nbsp;Quan Huang,&nbsp;Min Liu,&nbsp;Shengming Lu,&nbsp;Jinkang Chen* and Daijing Wei,&nbsp;","doi":"10.1021/acs.joc.5c0002210.1021/acs.joc.5c00022","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00022https://doi.org/10.1021/acs.joc.5c00022","url":null,"abstract":"<p >An unexpected electrochemical cascade reaction of 1,2,3-benzotriazinones with alkynes to assemble 3,4-dihydroisoquinolin-1(2<i>H</i>)-ones has been developed, which avoids the use of pressurized H<sub>2</sub>, any metal catalysts, and stoichiometric redox agents. This route tolerates a wide range of functional groups in both reactants and can be performed under an air atmosphere. The process of continuous cathodic reduction was demonstrated by control experiments and cyclic voltammograms. Moreover, the gram-scale reaction confirmed the potential of this environmentally benign method for practical applications.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"5862–5870 5862–5870"},"PeriodicalIF":3.3,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894212","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 Cascade Reactions of 1,2,3-Benzotriazinones with Alkynes to Assemble 3,4-Dihydroisoquinolin-1(2H)-ones 1,2,3-苯并三嗪酮与炔的电化学级联反应组装3,4-二氢异喹啉-1(2H)-酮
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-21 DOI: 10.1021/acs.joc.5c00022
Sanfei Nian, Xudong Wu, Anwu Chen, Zhiming Lei, Qiuyue Song, Quan Huang, Min Liu, Shengming Lu, Jinkang Chen, Daijing Wei
{"title":"Electrochemical Cascade Reactions of 1,2,3-Benzotriazinones with Alkynes to Assemble 3,4-Dihydroisoquinolin-1(2H)-ones","authors":"Sanfei Nian, Xudong Wu, Anwu Chen, Zhiming Lei, Qiuyue Song, Quan Huang, Min Liu, Shengming Lu, Jinkang Chen, Daijing Wei","doi":"10.1021/acs.joc.5c00022","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00022","url":null,"abstract":"An unexpected electrochemical cascade reaction of 1,2,3-benzotriazinones with alkynes to assemble 3,4-dihydroisoquinolin-1(2<i>H</i>)-ones has been developed, which avoids the use of pressurized H<sub>2</sub>, any metal catalysts, and stoichiometric redox agents. This route tolerates a wide range of functional groups in both reactants and can be performed under an air atmosphere. The process of continuous cathodic reduction was demonstrated by control experiments and cyclic voltammograms. Moreover, the gram-scale reaction confirmed the potential of this environmentally benign method for practical applications.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143853589","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
Substrate- and Reagent-Controlled Dimerization of Vinyl para-Quinone Methides 底物和试剂控制的乙烯基对醌二聚化反应
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-21 DOI: 10.1021/acs.joc.5c00123
Ryan G. Baker, Kyle D. Reichl, Michael J. Smith, Michael Ricca, Margaret A. Mickelberg, John A. Porco, Jr.
{"title":"Substrate- and Reagent-Controlled Dimerization of Vinyl para-Quinone Methides","authors":"Ryan G. Baker, Kyle D. Reichl, Michael J. Smith, Michael Ricca, Margaret A. Mickelberg, John A. Porco, Jr.","doi":"10.1021/acs.joc.5c00123","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00123","url":null,"abstract":"Substrate and reagent-controlled dimerization of vinyl <i>para</i>-quinone methides (VPQMs) is reported. When subjected to Brønsted acidic conditions, VPQM dimerization occurs via a formal 1,8-addition to provide griffipavixanthone (GPX)-type congeners. Under optimized Lewis acidic conditions, a change in regioselectivity affords limonene-containing dimers by a 1,6-addition/cyclization process. This divergent reactivity has been explored on several substrates of differing complexity, providing access to analogues of the natural product griffipavixanthone (GPX) as well as a range of novel, substituted limonene dimers.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143853590","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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