Herein, we revisit the reduction of esters to primary alcohols using sodium borohydride and aluminum chloride. Solvent selection proved critical. An improved, more convenient procedure has been developed by replacing conventional diglyme with DME (1,2-dimethoxyethane). Mild reaction conditions, good functional group compatibility, gram-scale reaction, and operational simplicity demonstrate the power of this protocol.
{"title":"Gram-scale reduction of esters to alcohols using AlCl3/NaBH4 revisited: Solvent effect, scope, and limitations","authors":"Hai-yang Chen , Eman Fayad , Dalal Nasser Binjawhar , Hua-Li Qin","doi":"10.1016/j.tet.2025.135102","DOIUrl":"10.1016/j.tet.2025.135102","url":null,"abstract":"<div><div>Herein, we revisit the reduction of esters to primary alcohols using sodium borohydride and aluminum chloride. Solvent selection proved critical. An improved, more convenient procedure has been developed by replacing conventional diglyme with DME (1,2-dimethoxyethane). Mild reaction conditions, good functional group compatibility, gram-scale reaction, and operational simplicity demonstrate the power of this protocol.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135102"},"PeriodicalIF":2.2,"publicationDate":"2025-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145765750","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 : 2025-12-14DOI: 10.1016/j.tet.2025.135105
Lisha Wu, Xue Li, DongXiang Yan, Kun Cao, Jiahong Li
An efficient method for symmetric aryl sulfides synthesis is reported. Using low-cost, readily available potassium xanthogenate as sulfur source, it reacts with aryl bromides under light, possibly via two EDA interactions. Potassium xanthogenate acts as electron donor in the first EDA complex and generates key thiophenolate anion. It accesses hard-to-obtain electron-deficient products, tolerates diverse functional groups, and opens new avenues for diaryl sulfides.
{"title":"Synthesis of symmetric aryl sulfides mediated by xanthates: Based on the EDA complex strategy","authors":"Lisha Wu, Xue Li, DongXiang Yan, Kun Cao, Jiahong Li","doi":"10.1016/j.tet.2025.135105","DOIUrl":"10.1016/j.tet.2025.135105","url":null,"abstract":"<div><div>An efficient method for symmetric aryl sulfides synthesis is reported. Using low-cost, readily available potassium xanthogenate as sulfur source, it reacts with aryl bromides under light, possibly via two EDA interactions. Potassium xanthogenate acts as electron donor in the first EDA complex and generates key thiophenolate anion. It accesses hard-to-obtain electron-deficient products, tolerates diverse functional groups, and opens new avenues for diaryl sulfides.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"191 ","pages":"Article 135105"},"PeriodicalIF":2.2,"publicationDate":"2025-12-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145786970","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 : 2025-12-14DOI: 10.1016/j.tet.2025.135093
Xuxue Zhang , Jiekun Zhu , Junfeng Teng , Chao Zhou , Hao Xu , Xiaolu Yin , Chenxi Li , Xiaoyi Jiang , Song Cao
An efficient CAN-mediated nitrooxylation-phosphorylation of α-(trifluoromethyl)styrenes with H-phosphonates and H-phosphine oxides was described. This novel difunctionalization reaction could enable the rapid incorporation of nitrooxy group and phosphoryl group into α-(trifluoromethyl)styrene in one step, affording the β-nitrooxy-β-trifluoromethyl-phosphonates and β-nitrooxy-β-trifluoromethyl-phosphine oxides in moderate to good yields.
{"title":"Cerium(IV)-mediated nitrooxylation-phosphorylation of α-(trifluoromethyl)styrenes with H-phosphonates and H-phosphine oxides","authors":"Xuxue Zhang , Jiekun Zhu , Junfeng Teng , Chao Zhou , Hao Xu , Xiaolu Yin , Chenxi Li , Xiaoyi Jiang , Song Cao","doi":"10.1016/j.tet.2025.135093","DOIUrl":"10.1016/j.tet.2025.135093","url":null,"abstract":"<div><div>An efficient CAN-mediated nitrooxylation-phosphorylation of α-(trifluoromethyl)styrenes with <em>H</em>-phosphonates and <em>H</em>-phosphine oxides was described. This novel difunctionalization reaction could enable the rapid incorporation of nitrooxy group and phosphoryl group into α-(trifluoromethyl)styrene in one step, affording the β-nitrooxy-β-trifluoromethyl-phosphonates and β-nitrooxy-β-trifluoromethyl-phosphine oxides in moderate to good yields.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135093"},"PeriodicalIF":2.2,"publicationDate":"2025-12-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145765751","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 : 2025-12-14DOI: 10.1016/j.tet.2025.135100
Shenao Qu , Yue Wang , Er-Qing Li
In this work, we report the phosphine-catalyzed [4 + 2] cycloaddition reaction between benzofuran-derived azadienes and conjugated dienes. This method provides an efficient approach for constructing benzofuran-fused nitrogen-containing heterocyclic skeletons. The reaction features unique regioselectivity, good yields, excellent diastereoselectivity and broad substrate scope. Moreover, the potential synthetic utility of this strategy is demonstrated through gram-scale experiment and subsequent synthetic transformation.
{"title":"Phosphine-catalyzed [4 + 2] cycloaddition of benzofuran-derived azadienes and conjugated dienes: Synthesis of 1,2,3,4-tetrahydrobenzofuro[3,2-b]pyridines","authors":"Shenao Qu , Yue Wang , Er-Qing Li","doi":"10.1016/j.tet.2025.135100","DOIUrl":"10.1016/j.tet.2025.135100","url":null,"abstract":"<div><div>In this work, we report the phosphine-catalyzed [4 + 2] cycloaddition reaction between benzofuran-derived azadienes and conjugated dienes. This method provides an efficient approach for constructing benzofuran-fused nitrogen-containing heterocyclic skeletons. The reaction features unique regioselectivity, good yields, excellent diastereoselectivity and broad substrate scope. Moreover, the potential synthetic utility of this strategy is demonstrated through gram-scale experiment and subsequent synthetic transformation.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"191 ","pages":"Article 135100"},"PeriodicalIF":2.2,"publicationDate":"2025-12-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145786971","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 : 2025-12-13DOI: 10.1016/j.tet.2025.135098
Gang Wang , Jianpeng Du , Jian Liu , Jiangtao Li , Xiaohua Wang , Lin Zhang , Yalan Feng , Minglan Ma
An unprecedented metal-free cyclization reaction of tetralone-derived β-ketothioamides with nitroallylic acetates was developed, which provided a powerful method for the synthesis of 2,3-dihydrothiazole-5-carboxylates. In the reaction, nitroallylic acetates used α,β-carbons rather than the β,γ-carbons to construct the five-membered thiazole ring. The protocol features good functional group tolerance, mild metal-free conditions and simple procedure.
{"title":"Synthesis of 2,3-dihydrothiazole-5-carboxylates via a domino reaction of tetralone-derived β-ketothioamides with nitroallylic acetates","authors":"Gang Wang , Jianpeng Du , Jian Liu , Jiangtao Li , Xiaohua Wang , Lin Zhang , Yalan Feng , Minglan Ma","doi":"10.1016/j.tet.2025.135098","DOIUrl":"10.1016/j.tet.2025.135098","url":null,"abstract":"<div><div>An unprecedented metal-free cyclization reaction of tetralone-derived <em>β</em>-ketothioamides with nitroallylic acetates was developed, which provided a powerful method for the synthesis of 2,3-dihydrothiazole-5-carboxylates. In the reaction, nitroallylic acetates used <em>α,β</em>-carbons rather than the <em>β,γ</em>-carbons to construct the five-membered thiazole ring. The protocol features good functional group tolerance, mild metal-free conditions and simple procedure.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"191 ","pages":"Article 135098"},"PeriodicalIF":2.2,"publicationDate":"2025-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145786967","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 : 2025-12-13DOI: 10.1016/j.tet.2025.135087
Siyi Qin , Mingyang Yang , Xun Yang, Jingshu Han, Haiyan Li, Wengui Duan, Lin Yu
Ligand-to-metal charge transfer (LMCT) photocatalysis has emerged as a transformative strategy in synthetic organic chemistry. This review summaries the synergistic integration of photoinduced LMCT processes with earth-abundant transition-metal catalysis, highlighting a sustainable paradigm that addresses longstanding challenges in organic synthesis. Unlike traditional photoredox systems that rely on expensive noble metal (such as ruthenium and iridium) complexes, LMCT photocatalysis utilizes complexes formed between organic ligands and first-row transition metals (iron, copper, cobalt, and lanthanide cerium), which generate reactive radical intermediates under mild conditions upon visible light irradiation. The combination of LMCT photocatalysis with transition-metal catalysis creates powerful dual platforms that enable challenging transformations by merging radical-generating capabilities with the coordination and bond-forming abilities of nickel, copper, cobalt, manganese, chromium, and titanium catalysts. These systems operate through sophisticated mechanisms where photogenerated radical species interact with transition metal centers to access novel reaction pathways inaccessible to either catalytic system alone. This review analyzes recent developments in dual LMCT/transition-metal catalytic systems, examining their mechanisms, substrate scope, functional group compatibility, and synthetic utility. We highlight how these sustainable catalytic platforms have enabled challenging cross-coupling reactions, C–H functionalizations, and cascade transformations under remarkably mild conditions. Finally, we discuss current limitations and opportunities in this rapidly evolving field, with particular emphasis on expanding reaction scope, enhancing stereoselectivity, and advancing green chemistry principles.
{"title":"Visible-light-induced ligand-to-metal charge transfer in synergistic catalysis with earth-abundant 3d transition metals: A new paradigm for sustainable organic synthesis","authors":"Siyi Qin , Mingyang Yang , Xun Yang, Jingshu Han, Haiyan Li, Wengui Duan, Lin Yu","doi":"10.1016/j.tet.2025.135087","DOIUrl":"10.1016/j.tet.2025.135087","url":null,"abstract":"<div><div>Ligand-to-metal charge transfer (LMCT) photocatalysis has emerged as a transformative strategy in synthetic organic chemistry. This review summaries the synergistic integration of photoinduced LMCT processes with earth-abundant transition-metal catalysis, highlighting a sustainable paradigm that addresses longstanding challenges in organic synthesis. Unlike traditional photoredox systems that rely on expensive noble metal (such as ruthenium and iridium) complexes, LMCT photocatalysis utilizes complexes formed between organic ligands and first-row transition metals (iron, copper, cobalt, and lanthanide cerium), which generate reactive radical intermediates under mild conditions upon visible light irradiation. The combination of LMCT photocatalysis with transition-metal catalysis creates powerful dual platforms that enable challenging transformations by merging radical-generating capabilities with the coordination and bond-forming abilities of nickel, copper, cobalt, manganese, chromium, and titanium catalysts. These systems operate through sophisticated mechanisms where photogenerated radical species interact with transition metal centers to access novel reaction pathways inaccessible to either catalytic system alone. This review analyzes recent developments in dual LMCT/transition-metal catalytic systems, examining their mechanisms, substrate scope, functional group compatibility, and synthetic utility. We highlight how these sustainable catalytic platforms have enabled challenging cross-coupling reactions, C–H functionalizations, and cascade transformations under remarkably mild conditions. Finally, we discuss current limitations and opportunities in this rapidly evolving field, with particular emphasis on expanding reaction scope, enhancing stereoselectivity, and advancing green chemistry principles.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"191 ","pages":"Article 135087"},"PeriodicalIF":2.2,"publicationDate":"2025-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145786965","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 : 2025-12-13DOI: 10.1016/j.tet.2025.135099
Aigui Zhang, Wenjing Luo, Zhonghua Qu, Weiqing Yang, Min Luo, Xin Li, Menglin Ma
N-Aryl-1,2,3-triazole compounds are important pharmaceutical motifs synthesized via nucleophile reactions with triazoles. Typically, both N2 and N1 regioisomers are produced simultaneously. In this article, a synergistic catalytic system comprising CuI and 1,2-diphenylethylenediamine (DPEN) was employed for the selective N2-coupling of 2-bromobenzoic acid with triazole. This reaction yielded 2-(2H-1,2,3-triazol-2-yl)benzoic acid (4a) with an impressive yield of 86 % and a regioselectivity of 91 % for the N2 isomer. Additionally, 2-bromobenzoic acid served as a cost-effective alternative to the traditionally used 2-iodobenzoic acid; notably, the reaction time was reduced from 4 h to 1.5 h. Mechanistic studies indicated that the DPEN ligand promotes carbon-copper bond formation, enhancing reaction activity and accelerating the overall rate; However, while there has been some improvement in N2 selectivity, it remains less than ideal.
n -芳基-1,2,3-三唑化合物是与三唑通过亲核反应合成的重要药物基序。通常，N2和N1区域异构体同时产生。本文采用由CuI和1,2-二苯乙二胺（DPEN）组成的协同催化体系进行了2-溴苯甲酸与三唑的选择性n2偶联反应。该反应生成2-（2h -1,2,3-三唑-2-基）苯甲酸（4a），其N2异构体的产率为86%，区域选择性为91%。此外，2-溴苯甲酸作为传统上使用的2-碘苯甲酸的一种具有成本效益的替代品；反应时间由4 h缩短至1.5 h。机理研究表明，DPEN配体促进了碳铜键的形成，提高了反应活性，加快了反应的总速率；然而，虽然对N2的选择性有了一定的提高，但仍然不够理想。
{"title":"Investigation of the N2-Selective functionalization reaction of 2H-1,2,3-triazole catalyzed by a synergistic combination of copper and diamine ligands","authors":"Aigui Zhang, Wenjing Luo, Zhonghua Qu, Weiqing Yang, Min Luo, Xin Li, Menglin Ma","doi":"10.1016/j.tet.2025.135099","DOIUrl":"10.1016/j.tet.2025.135099","url":null,"abstract":"<div><div><em>N</em>-Aryl-1,2,3-triazole compounds are important pharmaceutical motifs synthesized via nucleophile reactions with triazoles. Typically, both <em>N</em><sup><em>2</em></sup> and <em>N</em><sup><em>1</em></sup> regioisomers are produced simultaneously. In this article, a synergistic catalytic system comprising CuI and 1,2-diphenylethylenediamine (DPEN) was employed for the selective <em>N</em><sup><em>2</em></sup>-coupling of 2-bromobenzoic acid with triazole. This reaction yielded 2-(2<em>H</em>-1,2,3-triazol-2-yl)benzoic acid (<strong>4a</strong>) with an impressive yield of 86 % and a regioselectivity of 91 % for the <em>N</em><sup><em>2</em></sup> isomer. Additionally, 2-bromobenzoic acid served as a cost-effective alternative to the traditionally used 2-iodobenzoic acid; notably, the reaction time was reduced from 4 h to 1.5 h. Mechanistic studies indicated that the DPEN ligand promotes carbon-copper bond formation, enhancing reaction activity and accelerating the overall rate; However, while there has been some improvement in <em>N</em><sup><em>2</em></sup> selectivity, it remains less than ideal.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"191 ","pages":"Article 135099"},"PeriodicalIF":2.2,"publicationDate":"2025-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145786966","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 : 2025-12-12DOI: 10.1016/j.tet.2025.135091
Xi Xiang , Minghui Xie , Hongran Chen , Zixin Deng , Gen Li , Xiaohui Yan , Min Xu , Anwei Hou
Bacterial terpene synthases (TPSs) represent a valuable source of enzymatic diversity for the discovery of novel terpenoid structures. Here, we report the functional characterization of two diterpene synthases, GTC2 and E2E2, from Chitinophaga species. Heterologous expression and biochemical assays demonstrated that both enzymes can utilize farnesyl diphosphate (FPP) and geranylgeranyl diphosphate (GGPP) to produce distinct terpene profiles. Six diterpenes (5–10) were isolated, including two new compounds (8 and 9), for which their structures and relative configurations were elucidated and plausible formation mechanisms were proposed. Structural modeling, molecular docking, and mutagenesis revealed that residue Y293 plays a key role in determining the product specificity of E2E2. Y293 N substitution significantly altered the product profile, affording three known diterpenes (11–13), one of which (11) was confirmed by X-ray crystallography. This study expands the known diterpene diversity of Chitinophaga and provides insights into the structure–function relationship of bacterial diterpene synthases.
{"title":"Characterization of two diterpene synthases from Chitinophaga species","authors":"Xi Xiang , Minghui Xie , Hongran Chen , Zixin Deng , Gen Li , Xiaohui Yan , Min Xu , Anwei Hou","doi":"10.1016/j.tet.2025.135091","DOIUrl":"10.1016/j.tet.2025.135091","url":null,"abstract":"<div><div>Bacterial terpene synthases (TPSs) represent a valuable source of enzymatic diversity for the discovery of novel terpenoid structures. Here, we report the functional characterization of two diterpene synthases, GTC2 and E2E2, from <em>Chitinophaga</em> species. Heterologous expression and biochemical assays demonstrated that both enzymes can utilize farnesyl diphosphate (FPP) and geranylgeranyl diphosphate (GGPP) to produce distinct terpene profiles. Six diterpenes (<strong>5</strong>–<strong>10</strong>) were isolated, including two new compounds (<strong>8</strong> and <strong>9</strong>), for which their structures and relative configurations were elucidated and plausible formation mechanisms were proposed. Structural modeling, molecular docking, and mutagenesis revealed that residue Y293 plays a key role in determining the product specificity of E2E2. Y293 N substitution significantly altered the product profile, affording three known diterpenes (<strong>11</strong>–<strong>13</strong>), one of which (<strong>11</strong>) was confirmed by X-ray crystallography. This study expands the known diterpene diversity of <em>Chitinophaga</em> and provides insights into the structure–function relationship of bacterial diterpene synthases.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"191 ","pages":"Article 135091"},"PeriodicalIF":2.2,"publicationDate":"2025-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145786969","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 : 2025-12-11DOI: 10.1016/j.tet.2025.135096
Huabin Wang , Qiaoli Li , Feiyang Long , Tiantian Zhou , Zeyu Zhang , Songlin Zhang , Zhen Yao , Ying Zhou , Qiang Huang
An efficient and eco-friendly protocol to synthesize C2-phosphorylated 2,3-dihydrochromones was developed via Brønsted acid-promoted selective addition of chromones with H-phosphine oxides. The reaction exhibits a broad substrate scope, shows good compatibility with various functional groups, affords high yields and is amenable to gram - scale synthesis. This strategy, mediated by Brønsted acid, proceeded smoothly under mild and simple conditions without any metal catalyst or oxidant, providing an alternative approach to access C2-phosphorylated 2,3-dihydrochromones.
{"title":"Brønsted acid-promoted selective addition of chromones with H-phosphine oxides for synthesis of C2-Phosphorylated 2,3-2H-chromones","authors":"Huabin Wang , Qiaoli Li , Feiyang Long , Tiantian Zhou , Zeyu Zhang , Songlin Zhang , Zhen Yao , Ying Zhou , Qiang Huang","doi":"10.1016/j.tet.2025.135096","DOIUrl":"10.1016/j.tet.2025.135096","url":null,"abstract":"<div><div>An efficient and eco-friendly protocol to synthesize C2-phosphorylated 2,3-dihydrochromones was developed via Brønsted acid-promoted selective addition of chromones with H-phosphine oxides. The reaction exhibits a broad substrate scope, shows good compatibility with various functional groups, affords high yields and is amenable to gram - scale synthesis. This strategy, mediated by Brønsted acid, proceeded smoothly under mild and simple conditions without any metal catalyst or oxidant, providing an alternative approach to access C2-phosphorylated 2,3-dihydrochromones.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"191 ","pages":"Article 135096"},"PeriodicalIF":2.2,"publicationDate":"2025-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145786968","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 : 2025-12-11DOI: 10.1016/j.tet.2025.135088
Xiaoyu Liao , Zhiyun Zhao , Jiyi Lv , Xiling Deng , Xinrun Zhao , Yangzi Chen , Wei Zhang , Pinghua Sun , Xinhui Pan
An efficient copper(Ⅰ) bromide catalyzed 1,3-dipolar cycloaddition reaction of different α-nitroketones with dipolarophiles has been investigated. These reactions afford the corresponding 3-benzoylisoxazolines in moderate to high yields (up to 99.9 %) under mild conditions. This method provides an economical and simple route to construction of isoxazole or isoxazoline ring.
{"title":"Synthesis of 3-benzoylisoxazolines by copper(Ⅰ) bromide-catalyzed 1,3-dipolar cycloaddition of nitroketones with dipolarophiles","authors":"Xiaoyu Liao , Zhiyun Zhao , Jiyi Lv , Xiling Deng , Xinrun Zhao , Yangzi Chen , Wei Zhang , Pinghua Sun , Xinhui Pan","doi":"10.1016/j.tet.2025.135088","DOIUrl":"10.1016/j.tet.2025.135088","url":null,"abstract":"<div><div>An efficient copper(Ⅰ) bromide catalyzed 1,3-dipolar cycloaddition reaction of different α-nitroketones with dipolarophiles has been investigated. These reactions afford the corresponding 3-benzoylisoxazolines in moderate to high yields (up to 99.9 %) under mild conditions. This method provides an economical and simple route to construction of isoxazole or isoxazoline ring.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135088"},"PeriodicalIF":2.2,"publicationDate":"2025-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145838303","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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