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Straightforward Access to 4-Sulfenylated Isocoumarins via Sulfoxides/MOMCl-Enabled Regioselective Cleavage and Reconfiguration of C–S Bonds 通过硫氧化物/MOMCl 驱动的 C-S 键区域选择性裂解和重构，直接获得 4 磺化异香豆素
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1021/acs.joc.5c00287
Linlin Xing, Shiyan Cao, Hezhuang Feng, Haixia Zheng, Haoyuan Fan, Kai Wang, Yongjun Zheng, Yong Zhang, Yunfei Du
{"title":"Straightforward Access to 4-Sulfenylated Isocoumarins via Sulfoxides/MOMCl-Enabled Regioselective Cleavage and Reconfiguration of C–S Bonds","authors":"Linlin Xing, Shiyan Cao, Hezhuang Feng, Haixia Zheng, Haoyuan Fan, Kai Wang, Yongjun Zheng, Yong Zhang, Yunfei Du","doi":"10.1021/acs.joc.5c00287","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00287","url":null,"abstract":"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.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"33 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143858116","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
Visible-Light-Driven Tandem Cyclization of o-Hydroxyaryl Enaminones: Access to 3-(α-Arylsulfonamido)trifluoroethyl Chromones 邻羟基胺酮的可见光驱动串联环化：获得3-（α-芳基磺胺）三氟乙基色酮
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1021/acs.joc.5c00424
Jinwei Yuan, Qiyang Liu, Xuanlin Liu, Da Wang, Meng Yan, Xianghui Meng, Ji Ma, Lingbo Qu
{"title":"Visible-Light-Driven Tandem Cyclization of o-Hydroxyaryl Enaminones: Access to 3-(α-Arylsulfonamido)trifluoroethyl Chromones","authors":"Jinwei Yuan, Qiyang Liu, Xuanlin Liu, Da Wang, Meng Yan, Xianghui Meng, Ji Ma, Lingbo Qu","doi":"10.1021/acs.joc.5c00424","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00424","url":null,"abstract":"A visible-light-driven intermolecular tandem α-amidotrifluoroethylation/cyclization of enaminones using a previously unreported <i>N</i>-trifluoroethylaminopyridinium salt was achieved in the absence of transition metal catalysts or bases. Notable features of this synthetic method include mild conditions, high selectivity, excellent functional group compatibility, and satisfactory yields. Preliminary mechanistic studies indicate that the reaction proceeds via a radical pathway, involving an in situ generated <i>N</i>-trifluoroethyl radical, followed by a 1,2-H shift.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"2 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143858117","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
Typical Electron-Withdrawing Groups Are ortho, meta-Directors Rather than meta-Directors in Electrophilic Aromatic Substitution 亲电芳香取代中典型的吸电子基团是邻位、元导向而不是元导向
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1021/acs.joc.5c00426
Paul R. Rablen
{"title":"Typical Electron-Withdrawing Groups Are ortho, meta-Directors Rather than meta-Directors in Electrophilic Aromatic Substitution","authors":"Paul R. Rablen","doi":"10.1021/acs.joc.5c00426","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00426","url":null,"abstract":"Electron-withdrawing groups are traditionally considered <i>meta</i>-directing in aromatic substitution reactions. However, when the pre-existing substituent is a π-acceptor, both experiment and calculation indicate that substantial amounts of <i>ortho</i> as well as <i>meta</i> substitution occur, with very little <i>para</i> reactivity. A simple perturbative MO argument rationalizes this finding. It is therefore suggested that these substituents are best understood as <i>ortho</i>, <i>meta</i>-directors, with a preference for <i>meta</i>, just as electron-donating groups are considered <i>ortho</i>, <i>para</i>-directors, with a preference for <i>para</i>.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"75 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143858118","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
Typical Electron-Withdrawing Groups Are ortho, meta-Directors Rather than meta-Directors in Electrophilic Aromatic Substitution 亲电芳香取代中典型的吸电子基团是邻位、元导向而不是元导向
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1021/acs.joc.5c0042610.1021/acs.joc.5c00426
Paul R. Rablen*, 
{"title":"Typical Electron-Withdrawing Groups Are ortho, meta-Directors Rather than meta-Directors in Electrophilic Aromatic Substitution","authors":"Paul R. Rablen*,&nbsp;","doi":"10.1021/acs.joc.5c0042610.1021/acs.joc.5c00426","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00426https://doi.org/10.1021/acs.joc.5c00426","url":null,"abstract":"<p >Electron-withdrawing groups are traditionally considered <i>meta</i>-directing in aromatic substitution reactions. However, when the pre-existing substituent is a π-acceptor, both experiment and calculation indicate that substantial amounts of <i>ortho</i> as well as <i>meta</i> substitution occur, with very little <i>para</i> reactivity. A simple perturbative MO argument rationalizes this finding. It is therefore suggested that these substituents are best understood as <i>ortho</i>, <i>meta</i>-directors, with a preference for <i>meta</i>, just as electron-donating groups are considered <i>ortho</i>, <i>para</i>-directors, with a preference for <i>para</i>.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"6090–6093 6090–6093"},"PeriodicalIF":3.3,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.joc.5c00426","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894177","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Visible-Light-Driven Tandem Cyclization of o-Hydroxyaryl Enaminones: Access to 3-(α-Arylsulfonamido)trifluoroethyl Chromones 邻羟基胺酮的可见光驱动串联环化：获得3-（α-芳基磺胺）三氟乙基色酮
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1021/acs.joc.5c0042410.1021/acs.joc.5c00424
Jinwei Yuan*, Qiyang Liu, Xuanlin Liu, Da Wang, Meng Yan*, Xianghui Meng, Ji Ma* and Lingbo Qu, 
{"title":"Visible-Light-Driven Tandem Cyclization of o-Hydroxyaryl Enaminones: Access to 3-(α-Arylsulfonamido)trifluoroethyl Chromones","authors":"Jinwei Yuan*,&nbsp;Qiyang Liu,&nbsp;Xuanlin Liu,&nbsp;Da Wang,&nbsp;Meng Yan*,&nbsp;Xianghui Meng,&nbsp;Ji Ma* and Lingbo Qu,&nbsp;","doi":"10.1021/acs.joc.5c0042410.1021/acs.joc.5c00424","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00424https://doi.org/10.1021/acs.joc.5c00424","url":null,"abstract":"<p >A visible-light-driven intermolecular tandem α-amidotrifluoroethylation/cyclization of enaminones using a previously unreported <i>N</i>-trifluoroethylaminopyridinium salt was achieved in the absence of transition metal catalysts or bases. Notable features of this synthetic method include mild conditions, high selectivity, excellent functional group compatibility, and satisfactory yields. Preliminary mechanistic studies indicate that the reaction proceeds via a radical pathway, involving an in situ generated <i>N</i>-trifluoroethyl radical, followed by a 1,2-H shift.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"6031–6043 6031–6043"},"PeriodicalIF":3.3,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894272","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
Chemoselective Double Allylic Substitutions with Carbon Nucleophiles: Access to Tetrahydroindoles and Tetrahydrocarbazoles 亲核试剂的化学选择性双烯丙基取代：获得四氢吲哚和四氢咔唑
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1021/acs.joc.5c0012110.1021/acs.joc.5c00121
Bocheng Chen, Lucas Pagès, Cyrille Kouklovsky, Sébastien Prévost* and Aurélien de la Torre*, 
{"title":"Chemoselective Double Allylic Substitutions with Carbon Nucleophiles: Access to Tetrahydroindoles and Tetrahydrocarbazoles","authors":"Bocheng Chen,&nbsp;Lucas Pagès,&nbsp;Cyrille Kouklovsky,&nbsp;Sébastien Prévost* and Aurélien de la Torre*,&nbsp;","doi":"10.1021/acs.joc.5c0012110.1021/acs.joc.5c00121","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00121https://doi.org/10.1021/acs.joc.5c00121","url":null,"abstract":"<p >A chemoselective double allylic substitution involving two different carbon nucleophiles is described. The reaction relies on a dual catalytic approach, with a Lewis acid promoting the first allylic substitution and Pd promoting the second step. Starting from simple allylic diols, a diversity of polycyclic structures can be obtained, including tetrahydroindole, tetrahydrocarbazole, and tetrahydronaphthalene.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"6079–6083 6079–6083"},"PeriodicalIF":3.3,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894178","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
Visible-Light-Induced 4CzIPN-Catalyzed Alkylamination of Alkenes via Cyclobutanone Oxime Esters and Anilines 可见光诱导4czipn催化环丁酮肟酯和苯胺烷基化烯烃
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1021/acs.joc.4c02172
Jiang-Hong Liu, Ze-Yu Tian, Zhen-Ye Wu, Tian-Le Huang, Li Hai, Li Guo, Yong Wu, Zhongzhen Yang
{"title":"Visible-Light-Induced 4CzIPN-Catalyzed Alkylamination of Alkenes via Cyclobutanone Oxime Esters and Anilines","authors":"Jiang-Hong Liu, Ze-Yu Tian, Zhen-Ye Wu, Tian-Le Huang, Li Hai, Li Guo, Yong Wu, Zhongzhen Yang","doi":"10.1021/acs.joc.4c02172","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02172","url":null,"abstract":"We disclosed an organophotoredox-catalyzed three-component oxidative radical-polar crossover strategy for constructing 1,2-alkylamination products. Cycloketone oxime derivatives were used as cyanoalkyl radical precursors and anilines were used as the nucleophiles. This facile protocol shows a good reaction yield and broad substrate scope.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"18 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143862516","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
Chemoselective Double Allylic Substitutions with Carbon Nucleophiles: Access to Tetrahydroindoles and Tetrahydrocarbazoles 亲核试剂的化学选择性双烯丙基取代：获得四氢吲哚和四氢咔唑
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1021/acs.joc.5c00121
Bocheng Chen, Lucas Pagès, Cyrille Kouklovsky, Sébastien Prévost, Aurélien de la Torre
{"title":"Chemoselective Double Allylic Substitutions with Carbon Nucleophiles: Access to Tetrahydroindoles and Tetrahydrocarbazoles","authors":"Bocheng Chen, Lucas Pagès, Cyrille Kouklovsky, Sébastien Prévost, Aurélien de la Torre","doi":"10.1021/acs.joc.5c00121","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00121","url":null,"abstract":"A chemoselective double allylic substitution involving two different carbon nucleophiles is described. The reaction relies on a dual catalytic approach, with a Lewis acid promoting the first allylic substitution and Pd promoting the second step. Starting from simple allylic diols, a diversity of polycyclic structures can be obtained, including tetrahydroindole, tetrahydrocarbazole, and tetrahydronaphthalene.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"51 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143862544","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
Visible-Light-Mediated Addition Reactions of Sulfur-Containing Reagents with α-Trifluoromethyl Alkenes 含硫试剂与α-三氟甲基烯烃的可见光加成反应
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1021/acs.joc.5c0039610.1021/acs.joc.5c00396
Yi-Rong Chen, Jia-Hui Han, Weidong Rao, Ping Song*, Shu-su Shen, Daopeng Sheng and Shun-Yi Wang*, 
{"title":"Visible-Light-Mediated Addition Reactions of Sulfur-Containing Reagents with α-Trifluoromethyl Alkenes","authors":"Yi-Rong Chen,&nbsp;Jia-Hui Han,&nbsp;Weidong Rao,&nbsp;Ping Song*,&nbsp;Shu-su Shen,&nbsp;Daopeng Sheng and Shun-Yi Wang*,&nbsp;","doi":"10.1021/acs.joc.5c0039610.1021/acs.joc.5c00396","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00396https://doi.org/10.1021/acs.joc.5c00396","url":null,"abstract":"<p >Herein, we described the addition reactions of sulfur-containing reagents (sodium sulfinates, dithiosulfonates) with α-trifluoromethyl alkenes under visible light. A series of trifluoromethyl sulfonates were synthesized via the visible-light-induced radical addition reaction of sodium sulfinates and α-trifluoromethyl alkenes to obtain protons from the solvent. A series of dithiosulfonated derivatives were synthesized via visible-light-induced bifunctionalization reaction of α-trifluoromethyl alkenes with dithiosulfonates.This strategy has the advantages of mild reaction conditions, good substrate universality and high yield up to 99% yield.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"6013–6024 6013–6024"},"PeriodicalIF":3.3,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894244","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
Visible-Light-Mediated Addition Reactions of Sulfur-Containing Reagents with α-Trifluoromethyl Alkenes 可见光介导的含硫试剂与 α-三氟甲基烯的加成反应
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1021/acs.joc.5c00396
Yi-Rong Chen, Jia-Hui Han, Weidong Rao, Ping Song, Shu-su Shen, Daopeng Sheng, Shun-Yi Wang
{"title":"Visible-Light-Mediated Addition Reactions of Sulfur-Containing Reagents with α-Trifluoromethyl Alkenes","authors":"Yi-Rong Chen, Jia-Hui Han, Weidong Rao, Ping Song, Shu-su Shen, Daopeng Sheng, Shun-Yi Wang","doi":"10.1021/acs.joc.5c00396","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00396","url":null,"abstract":"Herein, we described the addition reactions of sulfur-containing reagents (sodium sulfinates, dithiosulfonates) with α-trifluoromethyl alkenes under visible light. A series of trifluoromethyl sulfonates were synthesized via the visible-light-induced radical addition reaction of sodium sulfinates and α-trifluoromethyl alkenes to obtain protons from the solvent. A series of dithiosulfonated derivatives were synthesized via visible-light-induced bifunctionalization reaction of α-trifluoromethyl alkenes with dithiosulfonates.This strategy has the advantages of mild reaction conditions, good substrate universality and high yield up to 99% yield.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"51 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143858115","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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