Pub Date : 2026-01-17DOI: 10.1016/j.tet.2026.135153
Sofia Kolyadina, Andrey Kruchinin, Mikhail Minyaev, Maxim Bastrakov, Alexey Starosotnikov
A number of novel 2-R-6-nitro[1,2,4]triazolo[1,5-a]pyrimidines were synthesized. Their reactions with neutral C-nucleophiles (1,3-dicarbonyl compounds, indoles, polyphenols) proceeded under mild conditions (room temperature, no base or catalyst) giving rise to stable 1,4-adducts to pyrimidine ring. On the basis of 7-amino-6-nitro[1,2,4]triazolo[1,5-a]pyrimidines, a method was developed for the preparation of the previously unknown heterocyclic systems, namely [1,2,4]triazolo[1,5-a]pyrimidines fused with 1,2,5-oxa-, thia- and selenadiazole rings. These new heterocycles were found to undergo facile dearomatization under the action of 1,3-dicarbonyl compounds and π-excessive (het)arenes to give 1,2-adducts to pyrimidine ring. The possibility of oxidative rearomatization of the obtained adducts under the action of DDQ was demonstrated.
合成了一些新型的2- r -6-硝基[1,2,4]三唑[1,5- A]嘧啶。它们与中性c -亲核试剂（1,3-二羰基化合物、吲哚、多酚）在温和条件下（室温、无碱或催化剂）反应，生成稳定的1,4-嘧啶环加合物。在7-氨基-6-硝基[1,2,4]三唑[1,5-a]嘧啶的基础上，开发了一种制备先前未知的杂环体系的方法，即[1,2,4]三唑[1,5-a]嘧啶与1,2,5-氧-、西亚-和硒二唑环融合。这些新杂环在1,3-二羰基化合物和π-过量（羟基）芳烃的作用下易发生脱芳反应，使1,2-加合物生成嘧啶环。结果表明，所得加合物在DDQ的作用下可能发生氧化重芳构化反应。
{"title":"Synthesis and nucleophilic dearomatization of novel [1,2,4]triazolo[1,5-a]pyrimidines","authors":"Sofia Kolyadina, Andrey Kruchinin, Mikhail Minyaev, Maxim Bastrakov, Alexey Starosotnikov","doi":"10.1016/j.tet.2026.135153","DOIUrl":"10.1016/j.tet.2026.135153","url":null,"abstract":"<div><div>A number of novel 2-R-6-nitro[1,2,4]triazolo[1,5-<em>a</em>]pyrimidines were synthesized. Their reactions with neutral C-nucleophiles (1,3-dicarbonyl compounds, indoles, polyphenols) proceeded under mild conditions (room temperature, no base or catalyst) giving rise to stable 1,4-adducts to pyrimidine ring. On the basis of 7-amino-6-nitro[1,2,4]triazolo[1,5-<em>a</em>]pyrimidines, a method was developed for the preparation of the previously unknown heterocyclic systems, namely [1,2,4]triazolo[1,5-<em>a</em>]pyrimidines fused with 1,2,5-oxa-, thia- and selenadiazole rings. These new heterocycles were found to undergo facile dearomatization under the action of 1,3-dicarbonyl compounds and π-excessive (het)arenes to give 1,2-adducts to pyrimidine ring. The possibility of oxidative rearomatization of the obtained adducts under the action of DDQ was demonstrated.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"193 ","pages":"Article 135153"},"PeriodicalIF":2.2,"publicationDate":"2026-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146023268","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A diastereoselective synthesis of the core skeleton of a natural dopamine dimer from catechol was accomplished in several
steps. The structure was charactered by 1H NMR, 13C NMR, HRMS and X-ray spectrum. The total synthesis of the core skeleton provides a tool for the SAR and pharmacology research of N-acyl dopamine dimers 13a-j.
{"title":"Diastereoselective synthesis of N-acyl dopamine dimers in Aspongopus","authors":"Linming Zuo , Xianheng Wang , Guoyi Lou , Changkuo Zhao","doi":"10.1016/j.tet.2026.135138","DOIUrl":"10.1016/j.tet.2026.135138","url":null,"abstract":"<div><div>A diastereoselective synthesis of the core skeleton of a natural dopamine dimer from catechol was accomplished in several</div><div>steps. The structure was charactered by <sup>1</sup>H NMR, <sup>13</sup>C NMR, HRMS and X-ray spectrum. The total synthesis of the <strong>core skeleton</strong> provides a tool for the SAR and pharmacology research of N-acyl dopamine dimers <strong>13a-j</strong>.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"193 ","pages":"Article 135138"},"PeriodicalIF":2.2,"publicationDate":"2026-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146023271","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2026-01-11DOI: 10.1016/j.tet.2026.135136
Chao Yao , Yan Zhao , Yangyang Ou , Tengyang Zhang , Yue-Ming Li
Chiral copper complex bearing binaphthyl-prolinol-imidazoline type tridentate ligand was effective in enantioselective Friedel-Crafts alkylation of indoles with cyclic N-sulfonyl ketimino esters. The catalyst system exhibited excellent catalytic activity (up to 95 % yield) and enantioselectivity (up to 96 % ee), affording a series of chiral cyclic α-amino acid ester derivatives under mild reaction conditions. In addition to different indoles, the catalyst system was also compatible with pyrrole and 1-naphthol. The scalability of the reaction was exemplified with a gram-scale reaction. A plausible reaction mechanism was proposed based on preliminary DFT calculation results.
{"title":"Enantioselective Friedel-Crafts alkylation of indoles with cyclic N-sulfonyl ketimino esters catalyzed by Cu(II) complex bearing binaphthyl-proline-imidazoline-based ligands","authors":"Chao Yao , Yan Zhao , Yangyang Ou , Tengyang Zhang , Yue-Ming Li","doi":"10.1016/j.tet.2026.135136","DOIUrl":"10.1016/j.tet.2026.135136","url":null,"abstract":"<div><div>Chiral copper complex bearing binaphthyl-prolinol-imidazoline type tridentate ligand was effective in enantioselective Friedel-Crafts alkylation of indoles with cyclic <em>N</em>-sulfonyl ketimino esters. The catalyst system exhibited excellent catalytic activity (up to 95 % yield) and enantioselectivity (up to 96 % ee), affording a series of chiral cyclic α-amino acid ester derivatives under mild reaction conditions. In addition to different indoles, the catalyst system was also compatible with pyrrole and 1-naphthol. The scalability of the reaction was exemplified with a gram-scale reaction. A plausible reaction mechanism was proposed based on preliminary DFT calculation results.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"193 ","pages":"Article 135136"},"PeriodicalIF":2.2,"publicationDate":"2026-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146023266","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2026-01-11DOI: 10.1016/j.tet.2026.135139
Qing-Miao Pu , Xue Ran , Si-Wei Chen , Ke-Jin Jiao , Xiao-Tong Gao
Sulfoximines represent a privileged structural motif in pharmaceuticals, agrochemicals, and materials science. The electrochemical transformation of sulfoximines has garnered considerable interest among chemists, as electrons serve as clean, sustainable, and traceless reagents to drive these reactions. With the resurgence of electrochemical synthesis, many innovative and intriguing strategies have been developed for the synthesis of structurally diverse sulfoximines. This review systematically summarizes recent advances in this field according to the type of bond formed, including N–C, N–S, and N–P bonds. By highlighting representative examples and mechanistic insights, we aim to outline current trends and future challenges in this emerging area.
{"title":"Recent advances in electrochemical transformation of sulfoximines","authors":"Qing-Miao Pu , Xue Ran , Si-Wei Chen , Ke-Jin Jiao , Xiao-Tong Gao","doi":"10.1016/j.tet.2026.135139","DOIUrl":"10.1016/j.tet.2026.135139","url":null,"abstract":"<div><div>Sulfoximines represent a privileged structural motif in pharmaceuticals, agrochemicals, and materials science. The electrochemical transformation of sulfoximines has garnered considerable interest among chemists, as electrons serve as clean, sustainable, and traceless reagents to drive these reactions. With the resurgence of electrochemical synthesis, many innovative and intriguing strategies have been developed for the synthesis of structurally diverse sulfoximines. This review systematically summarizes recent advances in this field according to the type of bond formed, including N–C, N–S, and N–P bonds. By highlighting representative examples and mechanistic insights, we aim to outline current trends and future challenges in this emerging area.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"193 ","pages":"Article 135139"},"PeriodicalIF":2.2,"publicationDate":"2026-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145974194","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2026-01-10DOI: 10.1016/j.tet.2026.135137
Junjie Wang , Wenhui Chen , Yue Zhang , Fenglan Xiong , Zhibin Chen , Jing Zhan , Xianrong Cai , Xiaoxue Yue , Xiaoyan Ma
N-Substituted cycloalkanes represent privileged scaffolds in numerous alkaloids and pharmacologically active molecules. However, synthetic access to these structures has been largely limited to monocyclic systems. In this work, the annulation of six kinds of enamides with an aromatic propargyl ester catalyzed by IPrAuCl/AgSbF6 was systematically investigated, with particular focus on the effects of electronic and structural attributes on the resulting cyclization modes, and [2 + 3] and [2 + 1] annulation products were successfully obtained in good yields.
n -取代环烷烃在许多生物碱和具有药理活性的分子中具有特殊的支架结构。然而，这些结构的合成途径在很大程度上仅限于单环系统。本文系统地研究了IPrAuCl/AgSbF6催化芳香族丙炔酯对六种酰胺的环化反应，重点研究了电子属性和结构属性对环化产物的影响，并成功地获得了产率较高的[2 + 3]和[2 + 1]环化产物。
{"title":"Annulation of diverse enamides with an aromatic propargyl ester","authors":"Junjie Wang , Wenhui Chen , Yue Zhang , Fenglan Xiong , Zhibin Chen , Jing Zhan , Xianrong Cai , Xiaoxue Yue , Xiaoyan Ma","doi":"10.1016/j.tet.2026.135137","DOIUrl":"10.1016/j.tet.2026.135137","url":null,"abstract":"<div><div>N-Substituted cycloalkanes represent privileged scaffolds in numerous alkaloids and pharmacologically active molecules. However, synthetic access to these structures has been largely limited to monocyclic systems. In this work, the annulation of six kinds of enamides with an aromatic propargyl ester catalyzed by IPrAuCl/AgSbF<sub>6</sub> was systematically investigated, with particular focus on the effects of electronic and structural attributes on the resulting cyclization modes, and [2 + 3] and [2 + 1] annulation products were successfully obtained in good yields.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"193 ","pages":"Article 135137"},"PeriodicalIF":2.2,"publicationDate":"2026-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145974196","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A Palladium-catalyzed site-selective difluoroalkylation of 8-aminoquinoline amides has been described. This approach enables the efficient synthesis of C5-difluoroalkylated products from a broad range of 8-aminoquinoline amides under mild conditions, exhibiting excellent functional group tolerance. Preliminary mechanistic studies suggest that the reaction involves a free radical pathway. This strategy offers a new and practical for the synthesis of difluoroalkylation heterocycles.
{"title":"Palladium-catalyzed remote selective C5–H difluoroalkylation of 8-aminoquinoline amides with triethoxysilane as reductant","authors":"Weiwei Lv, Hao Luo, Qiaoyun Li, Wanying Yang, Yijing Chen, Xueting Zhu, Huihui Chen, Jiaxu Li","doi":"10.1016/j.tet.2026.135131","DOIUrl":"10.1016/j.tet.2026.135131","url":null,"abstract":"<div><div>A Palladium-catalyzed site-selective difluoroalkylation of 8-aminoquinoline amides has been described. This approach enables the efficient synthesis of C5-difluoroalkylated products from a broad range of 8-aminoquinoline amides under mild conditions, exhibiting excellent functional group tolerance. Preliminary mechanistic studies suggest that the reaction involves a free radical pathway. This strategy offers a new and practical for the synthesis of difluoroalkylation heterocycles.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"193 ","pages":"Article 135131"},"PeriodicalIF":2.2,"publicationDate":"2026-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145922627","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2026-01-08DOI: 10.1016/j.tet.2026.135135
Jin-Qiu You , Yun-Qi Jin , Chun-Yang Zhang , Wei-Zhen Huang
Tinosagitines A (1) and B (2), two previously undescribed clerodane diterpenoids, were isolated from the rhizomes of Tinospora sagittata. Compound 1 is a rare 19-nor-clerodane diterpenoid featuring a 6/6-fused ring system, while compound 2 represents the first example of clerodane diterpenoid characterized by a unique trans-6/6-fused ring system with highly oxidization in Tinospora sagittata plants. Their structures were determined through comprehensive spectroscopic analysis, including NMR spectroscopy, HRESIMS, and electronic circular dichroism (ECD) calculations. The inhibitory activities on death-associated protein kinase-related apoptosis-inducing kinase 2 (DRAK2) were evaluated, but both of them were inactive.
{"title":"Tinosagitines A and B, two modified clerodane diterpenoids from the rhizomes of Tinospora sagittata","authors":"Jin-Qiu You , Yun-Qi Jin , Chun-Yang Zhang , Wei-Zhen Huang","doi":"10.1016/j.tet.2026.135135","DOIUrl":"10.1016/j.tet.2026.135135","url":null,"abstract":"<div><div>Tinosagitines A (<strong>1</strong>) and B (<strong>2</strong>), two previously undescribed clerodane diterpenoids, were isolated from the rhizomes of <em>Tinospora sagittata</em>. Compound <strong>1</strong> is a rare 19-nor-clerodane diterpenoid featuring a 6/6-fused ring system, while compound <strong>2</strong> represents the first example of clerodane diterpenoid characterized by a unique <em>trans-</em>6/6-fused ring system with highly oxidization in <em>Tinospora sagittata</em> plants. Their structures were determined through comprehensive spectroscopic analysis, including NMR spectroscopy, HRESIMS, and electronic circular dichroism (ECD) calculations. The inhibitory activities on death-associated protein kinase-related apoptosis-inducing kinase 2 (DRAK2) were evaluated, but both of them were inactive.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"193 ","pages":"Article 135135"},"PeriodicalIF":2.2,"publicationDate":"2026-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145922628","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
In the present study, a three-phase system (EtOAc-water-EtOAc) for visible photocatalytic reduction of nitroaromatic compounds using β-CD-TiO2 was used. Also, for the first time, a comparison of water and magnetized water was investigated. Various factors such as amounts of TiO2, β-CD, PEG-400, light, time, and solvent were considered. Additionally, the phase-transfer catalytic character of β-CD- TiO2 was studied through transport tests. The UV–visible spectroscopic analysis supports higher solubility of nitroaromatic starting materials in magnetized water compared to deionized water. Analyses of the β-CD-TiO2 photocatalyst, including TEM, FESEM, EDAX-mapping, TGA, BET, DLS and ATR-FTIR were performed. Tuning of reaction conditions for obtaining valuable salicyl imine-based compounds in one-pot synthesis was performed. A practical scale of starting materials, short reaction time, fewer side reactions, simple separation of products and efficient one-pot synthesis of valuable salicyl imines are achievements of this three-phase system.
{"title":"A three phase photocatalytic system for practical one pot synthesis of salicyl imines from nitroaromatic compounds in magnetized water","authors":"Amir Farkhondeh , Foad Kazemi , Mostafa Gholizadeh , Babak Kaboudin","doi":"10.1016/j.tet.2026.135133","DOIUrl":"10.1016/j.tet.2026.135133","url":null,"abstract":"<div><div>In the present study, a three-phase system (EtOAc-water-EtOAc) for visible photocatalytic reduction of nitroaromatic compounds using β-CD-TiO<sub>2</sub> was used. Also, for the first time, a comparison of water and magnetized water was investigated. Various factors such as amounts of TiO<sub>2</sub>, β-CD, PEG-400, light, time, and solvent were considered. Additionally, the phase-transfer catalytic character of β-CD- TiO<sub>2</sub> was studied through transport tests. The UV–visible spectroscopic analysis supports higher solubility of nitroaromatic starting materials in magnetized water compared to deionized water. Analyses of the β-CD-TiO<sub>2</sub> photocatalyst, including TEM, FESEM, EDAX-mapping, TGA, BET, DLS and ATR-FTIR were performed. Tuning of reaction conditions for obtaining valuable salicyl imine-based compounds in one-pot synthesis was performed. A practical scale of starting materials, short reaction time, fewer side reactions, simple separation of products and efficient one-pot synthesis of valuable salicyl imines are achievements of this three-phase system.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"193 ","pages":"Article 135133"},"PeriodicalIF":2.2,"publicationDate":"2026-01-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145922626","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2026-01-06DOI: 10.1016/j.tet.2026.135132
Zhaobo Fu , Zhaonian Zhang , Qian Zhang , Zeguo Fang , Dong Li
A novel palladium-catalyzed aminocarbonylation of vinyl bromides with formic acid and carbodiimides has been developed, providing direct access to α,β-unsaturated amides under CO-free conditions. This transformation is enabled by a substrate-interchange strategy that integrates the complementary features of two previously reported aminocarbonylation systems. The protocol exhibits a broad substrate scope, tolerating both α- and β-bromoalkenes as well as a variety of functional groups, and can be readily scaled to gram quantities. Mechanistic studies suggest that the transformation proceeds via an ionic pathway.
{"title":"Palladium-catalyzed aminocarbonylation of vinyl bromides with formic acid and carbodiimides to access α,β-Unsaturated amides","authors":"Zhaobo Fu , Zhaonian Zhang , Qian Zhang , Zeguo Fang , Dong Li","doi":"10.1016/j.tet.2026.135132","DOIUrl":"10.1016/j.tet.2026.135132","url":null,"abstract":"<div><div>A novel palladium-catalyzed aminocarbonylation of vinyl bromides with formic acid and carbodiimides has been developed, providing direct access to <em>α,β</em>-unsaturated amides under CO-free conditions. This transformation is enabled by a substrate-interchange strategy that integrates the complementary features of two previously reported aminocarbonylation systems. The protocol exhibits a broad substrate scope, tolerating both <em>α</em>- and <em>β</em>-bromoalkenes as well as a variety of functional groups, and can be readily scaled to gram quantities. Mechanistic studies suggest that the transformation proceeds via an ionic pathway.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"193 ","pages":"Article 135132"},"PeriodicalIF":2.2,"publicationDate":"2026-01-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145922701","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
An efficient and environmentally benign protocol for the synthesis of 4,4-difluoro-3-hydroxy-3,4-dihydroisoquinolin-1(2H)-ones via Rh(III)-catalyzed C–H activation of N-methoxybenzamides with 2,2-difluorovinyl tosylate in water has been developed. This strategy utilizes water as a green reaction medium, demonstrating good functional group tolerance and providing the target products in moderate to good yields. The reaction proceeds under mild conditions, highlighting the potential of aqueous-phase C–H activation for constructing valuable fluorinated heterocycles. The practicality of this method was further validated by gram-scale synthesis and diverse derivatizations of the products.
{"title":"Synthesis of 4,4-difluoro-3-Hydroxy-3,4-dihydroisoquinolinones via Rh-catalyzed C–H activation of benzamides with 2,2-difluorovinyl tosylate in water","authors":"Shai Fang , Zhenli Luo , Huixuan Zhu , Cheng Jiang , Jing Qu , Jia-Qiang Wu","doi":"10.1016/j.tet.2026.135134","DOIUrl":"10.1016/j.tet.2026.135134","url":null,"abstract":"<div><div>An efficient and environmentally benign protocol for the synthesis of 4,4-difluoro-3-hydroxy-3,4-dihydroisoquinolin-1(2H)-ones via Rh(III)-catalyzed C–H activation of N-methoxybenzamides with 2,2-difluorovinyl tosylate in water has been developed. This strategy utilizes water as a green reaction medium, demonstrating good functional group tolerance and providing the target products in moderate to good yields. The reaction proceeds under mild conditions, highlighting the potential of aqueous-phase C–H activation for constructing valuable fluorinated heterocycles. The practicality of this method was further validated by gram-scale synthesis and diverse derivatizations of the products.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"193 ","pages":"Article 135134"},"PeriodicalIF":2.2,"publicationDate":"2026-01-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145922625","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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