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An efficient method for constructing C3-stannyl-tetrahydroquinoline: cascade hydroboration and hydrostannation of quinoline. 构建c3 -锡基-四氢喹啉的一种有效方法：喹啉的级联硼酸氢和氢锡化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-21 DOI: 10.1039/d5ob00369e
Tianwei Liu, Jianghua He, Yuetao Zhang
{"title":"An efficient method for constructing C3-stannyl-tetrahydroquinoline: cascade hydroboration and hydrostannation of quinoline.","authors":"Tianwei Liu, Jianghua He, Yuetao Zhang","doi":"10.1039/d5ob00369e","DOIUrl":"https://doi.org/10.1039/d5ob00369e","url":null,"abstract":"<p><p>Given the ability of carbon-tin bonds to undergo multiple transformations and the widespread application of C3-functionalized tetrahydroquinoline in the fields of pharmaceuticals, agrochemicals, and organic synthesis, the construction of C3-stannyl-tetrahydroquinoline holds significant importance. Guided by the hard-soft acid-base theory (HSAB), we used borane as hard acid to selectively reduce the hard base carbon-nitrogen double bonds in quinoline. In contrast, the soft acid hydrostannane is effective for reducing soft base carbon-carbon double bonds in quinoline. By using hydroborane and hydrostannane as co-reducing agents to reduce quinoline in the presence of B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> as a catalyst, a series of novel and potentially important <i>N</i>-borylated-C3-stannyl-tetrahydroquinoline compounds can be obtained with high yields (up to 98%) and selectivity (100%) at room temperature within 2 h. Based on the characterization of key intermediates by a series of <i>in situ</i> NMR reactions and detailed experimental data, we proposed the key to this selective cascade reaction. The hard acid, HBcat, reacts rapidly with the hard base, carbon-nitrogen double bonds in quinoline, to form a Lewis acid-base adduct, which, in the presence of B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>, leads to the formation of <i>N</i>-borylated dihydroquinolines. This reaction is less feasible for the soft acid (<sup><i>n</i></sup>Bu)<sub>3</sub>SnH. The soft acid (<sup><i>n</i></sup>Bu)<sub>3</sub>SnH, activated by B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>, tends to attack soft base carbon-carbon double bonds in <i>N</i>-borylated dihydroquinolines and give the final selective products. Additionally, the ability to obtain allylamine derivatives after the product has been modified further confirms its potential application value.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144109176","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}
引用次数: 0
Expanding the bioorthogonal chemistry toolbox: innovative synthetic strategies for cyclooctynes. 扩展生物正交化学工具箱：环新素的创新合成策略。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-21 DOI: 10.1039/d5ob00456j
Andrea Diana, Giuseppina I Truglio, Elena Petricci, Daniela Lanari
{"title":"Expanding the bioorthogonal chemistry toolbox: innovative synthetic strategies for cyclooctynes.","authors":"Andrea Diana, Giuseppina I Truglio, Elena Petricci, Daniela Lanari","doi":"10.1039/d5ob00456j","DOIUrl":"https://doi.org/10.1039/d5ob00456j","url":null,"abstract":"<p><p>Cyclooctyne derivatives represent an important class of compounds that play a key role in bioorthogonal chemistry. The presence of an endocyclic triple bond endows these molecules with the necessary reactivity for strain-promoted azide-alkyne cycloaddition (SPAAC); however, stability issues may hamper their use in biological systems. Many research groups, with the aid of computational studies, are devoting their efforts to finding ideal cyclooctyne candidates that strike a delicate balance between reactivity and stability. In this context, providing reliable and general synthetic procedures for accessing such chemical scaffolds is of critical importance. This review covers the recent synthetic strategies found in the literature to achieve this goal. Specifically, six main methodologies are discussed, highlighting the synthetic pathways, the key precursors for each, the applicability to a wide range of cyclooctyne derivatives and the challenges encountered in fulfilling this target.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144109179","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}
引用次数: 0
Phosphine-catalyzed reaction of cyclopropenones with water: divergent synthesis of highly functionalized γ-butenolides, trisubstituted α,β-unsaturated acids and anhydride. 膦催化环丙烯与水的反应：高功能化γ-丁烯内酯、三取代α、β-不饱和酸和酸酐的发散合成。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-20 DOI: 10.1039/d5ob00306g
Fujuan Li, Danna Yang, Hongyan Qu, Mingqi Zhu, Suqing Zheng
{"title":"Phosphine-catalyzed reaction of cyclopropenones with water: divergent synthesis of highly functionalized γ-butenolides, trisubstituted α,β-unsaturated acids and anhydride.","authors":"Fujuan Li, Danna Yang, Hongyan Qu, Mingqi Zhu, Suqing Zheng","doi":"10.1039/d5ob00306g","DOIUrl":"https://doi.org/10.1039/d5ob00306g","url":null,"abstract":"<p><p>The reaction between cyclopropenones and water catalyzed by different phosphines has been thoroughly investigated. Under the catalysis of trimethylphosphine, highly functionalized γ-butenolides were successfully synthesized from the simple starting material, cyclopropenones, and water in 35%-81% yields with excellent diastereoselectivities. Under the catalysis of triphenylphosphine, cyclopropenones were transferred to trisubstituted α,β-unsaturated acids with sufficient water in 78%-99% yields, while α,β-unsaturated acid anhydrides were obtained with trace water.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144101041","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}
引用次数: 0
Photo-induced aerobic cross-coupling of quinoxalin-2(1H)-ones with electron-rich thiophenes. 喹啉-2(1H)- 1与富电子噻吩的光诱导好氧交叉偶联。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-20 DOI: 10.1039/d5ob00557d
Wei Huang, Tong Wang, Shu-Ying Chen, Quan Zhou, Lei Wang
{"title":"Photo-induced aerobic cross-coupling of quinoxalin-2(1<i>H</i>)-ones with electron-rich thiophenes.","authors":"Wei Huang, Tong Wang, Shu-Ying Chen, Quan Zhou, Lei Wang","doi":"10.1039/d5ob00557d","DOIUrl":"https://doi.org/10.1039/d5ob00557d","url":null,"abstract":"<p><p>Herein, an economical and efficient protocol was developed for the aerobic oxidative cross-coupling of electron-rich thiophenes and quinoxazolines with the activation of two C-H bonds. No external photosensitizer was necessary for constructing the thiophenyl-quinoxazoline backbone. The substrate scope demonstrated the good functional tolerance of quinoxalin-2(1<i>H</i>)-ones, and suitable thiophenes for this coupling fall within the special spectrum of oxidative potentials lower than +1.50 V <i>vs.</i> SCE.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144101043","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}
引用次数: 0
Enantioselective access to 3,3'-disubstituted oxindole derivatives by N-heterocyclic carbene catalysis. n -杂环碳催化对映选择性获得3,3'-二取代氧化吲哚衍生物。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-20 DOI: 10.1039/d5ob00374a
Xiaomei Wang, Weixing Zeng, Shi-Wu Li, Jixin Pian, Zhifei Zhao
{"title":"Enantioselective access to 3,3'-disubstituted oxindole derivatives by N-heterocyclic carbene catalysis.","authors":"Xiaomei Wang, Weixing Zeng, Shi-Wu Li, Jixin Pian, Zhifei Zhao","doi":"10.1039/d5ob00374a","DOIUrl":"https://doi.org/10.1039/d5ob00374a","url":null,"abstract":"<p><p>An effectively enantioselective and regioselective N-heterocyclic carbene-catalyzed oxidative spiroannulation of isatin-derived enals with 2,4-dioxoesters to directly synthesize spirooxindole δ-lactones was realized. Subsequently, upon treatment with methanol under reflux, spirooxindole δ-lactones were effectively converted into acyclic 3,3'-disubstituted oxindole derivatives bearing an all-carbon quaternary center that might have been obtained through a novel sequence of deesterification and decarbonylation paths. This approach was qualified with a broad substrate scope and mild reaction conditions, achieving moderate to excellent yield and enantioselectivity. In addition, scale-up experiments and the synthetic transformations of spirooxindole δ-lactones and acyclic 3,3'-disubstituted oxindole derivatives further highlighted the synthetic utility.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144101033","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}
引用次数: 0
Pd-catalyzed decarboxylative coupling of zinc polyfluorobenzoate with aryl imidazolylsulfonate for polyfluorinated biaryl synthesis. 聚氟苯甲酸锌与芳基咪唑磺酸盐催化脱羧偶联合成多氟联芳基。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-20 DOI: 10.1039/d5ob00528k
Chao Gui, Yun Zhou, Hong-Fei Tian, Xue-Qiang Chu, Hao Xu, Chengping Miao, Weidong Rao, Zhi-Liang Shen
{"title":"Pd-catalyzed decarboxylative coupling of zinc polyfluorobenzoate with aryl imidazolylsulfonate for polyfluorinated biaryl synthesis.","authors":"Chao Gui, Yun Zhou, Hong-Fei Tian, Xue-Qiang Chu, Hao Xu, Chengping Miao, Weidong Rao, Zhi-Liang Shen","doi":"10.1039/d5ob00528k","DOIUrl":"https://doi.org/10.1039/d5ob00528k","url":null,"abstract":"<p><p>We report here an efficient decarboxylative cross-coupling of zinc polyfluorobenzoates with aryl imidazolylsulfonates under palladium catalysis, which proceeded effectively <i>via</i> C-O bond cleavage to afford the corresponding valuable polyfluorinated biaryls in moderate to good yields, exhibiting both reasonable substrate scope and broad functional group tolerance. In addition, late-stage functionalization of bioactive molecules and an amino acid-derived compound and scaled-up synthesis could be accomplished as well. Further exploration revealed that zinc polyfluorobenzoates are more vibrant than their potassium, sodium, and magnesium counterparts as a polyfluoroarylating reagent.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144101037","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}
引用次数: 0
Strategies for the optimisation of troublesome peptide nucleic acid (PNA) sequences. 棘手的肽核酸（PNA）序列优化策略。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-20 DOI: 10.1039/d5ob00589b
Emma E Watson
{"title":"Strategies for the optimisation of troublesome peptide nucleic acid (PNA) sequences.","authors":"Emma E Watson","doi":"10.1039/d5ob00589b","DOIUrl":"https://doi.org/10.1039/d5ob00589b","url":null,"abstract":"<p><p>Through the use of a pseudo-peptidic backbone, peptide nucleic acids (PNA) mimic the functionality of native nucleic acids while enjoying improved binding affinity and metabolic stability. However, many aspects of the application of PNA to biological and medicinal settings still requires sequence specific optimisation. This review highlights key areas for refinement, including synthesis, tuning of physical properties, cell permeability and analysis, including common strategies for the pracitioner to apply in each area.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144101072","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}
引用次数: 0
Visible-light-induced dearomative 1,4-carbamoylpyridinylation of nonactivated naphthalenes. 可见光诱导非活化萘的1,4-氨基甲酰吡啶脱芳化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-20 DOI: 10.1039/d5ob00550g
Cheng-An Jin, Hao Liu, Bo-Wen Xie, Ren-Xiao Liang, Yi-Xia Jia
{"title":"Visible-light-induced dearomative 1,4-carbamoylpyridinylation of nonactivated naphthalenes.","authors":"Cheng-An Jin, Hao Liu, Bo-Wen Xie, Ren-Xiao Liang, Yi-Xia Jia","doi":"10.1039/d5ob00550g","DOIUrl":"https://doi.org/10.1039/d5ob00550g","url":null,"abstract":"<p><p>A visible-light-induced dearomative 1,4-carbamoylpyridinylation of nonactivated naphthalenes is described. The protocol provides rapid access to a series of pyridinylated spiro 1,2-dihydronaphthalenes in moderate yields by using naphthyl-substituted oxamic acids and 4-cyanopyridines as substrates through radical-radical cross-coupling followed by base-mediated alkene tautomerization. In addition, this method enabled late-stage functionalization of several drug derivatives, demonstrating the practical utility of this reaction.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144101075","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}
引用次数: 0
Cu-β-CD-catalyzed Csp-P coupling of alkynes with dialkylphosphites and phosphine oxides. Cu-β- cd催化Csp-P与二烷基亚磷酸酯和氧化膦的偶联。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-20 DOI: 10.1039/d5ob00543d
Babak Kaboudin, Elahe Yousefian Amirkhiz, Ali Sabzalipour, Fahimeh Varmaghani, Tianjian Zhang, Yanlong Gu
{"title":"Cu-β-CD-catalyzed C<sub>sp</sub>-P coupling of alkynes with dialkylphosphites and phosphine oxides.","authors":"Babak Kaboudin, Elahe Yousefian Amirkhiz, Ali Sabzalipour, Fahimeh Varmaghani, Tianjian Zhang, Yanlong Gu","doi":"10.1039/d5ob00543d","DOIUrl":"https://doi.org/10.1039/d5ob00543d","url":null,"abstract":"<p><p>In this study, an easily accessible Cu-β-CD complex has been introduced for C-P cross-coupling reactions. The Cu-β-CD complex was used to catalyze the C-P coupling of alkynes with both dialkylphosphites and phosphinoxides for the synthesis of alkynyl-phosphonates and -phosphinoxides. The results showed that the coupling reactions could be carried out with appropriate yields for both aryl and alkyl alkynes. The applicability of Cu-β-CD for the oxidative decarboxylative coupling of phenylpropiolic acid with dialkyl phosphites and diphenylphosphine oxide was also studied. XPS and cyclic voltammetry analysis of the catalyst confirmed the presence of both Cu(I) and Cu(II) in the complex structure. The reaction proceeded <i>via</i> the oxidative addition of dialkyl phosphites and alkynes to the catalyst, and the final C-P cross-coupling product was obtained by a reductive elimination process. The presented catalytic method allows the easier and more cost-efficient cross-coupling of alkynes with dialkylphosphites and phosphine oxides under mild and base-free conditions.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144109178","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}
引用次数: 0
Cu(II)-SBA-15 mediated synthesis of 2-aryl benzimidazoles and benzoxazoles: a sustainable approach. Cu(II)-SBA-15介导的2-芳基苯并咪唑和苯并恶唑的可持续合成方法。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-20 DOI: 10.1039/d5ob00186b
Athira M P, Arun R, Suja Haridas
{"title":"Cu(II)-SBA-15 mediated synthesis of 2-aryl benzimidazoles and benzoxazoles: a sustainable approach.","authors":"Athira M P, Arun R, Suja Haridas","doi":"10.1039/d5ob00186b","DOIUrl":"https://doi.org/10.1039/d5ob00186b","url":null,"abstract":"<p><p>Benzimidazole and benzoxazole scaffolds are widely recognized for their presence in molecules with diverse pharmacological activities, including antiviral, antiulcer, antihypertensive, and anticancer effects. Motivated by their structural and synthetic significance, this work presents a green and efficient approach for the synthesis of 2-aryl benzimidazoles and benzoxazoles <i>via</i> the condensation of <i>o</i>-phenylenediamine or <i>o</i>-aminophenol with substituted benzaldehydes. The reaction is catalysed by Cu(II)-SBA-15, a recyclable and eco-friendly heterogeneous catalyst, offering an environmentally benign alternative to conventional methods. The catalytic system demonstrated a pristine reaction profile, with 100% conversion and 74-86% yields in a short timeframe. The heterogeneous mesoporous Cu-SBA-15 catalyst exhibited easy separability through simple centrifugation/filtration, emerging as a promising catalyst for the efficient and facile synthesis of 2-aryl benzimidazoles and 2-aryl benzoxazoles. Significantly, the catalyst demonstrated broad substrate scope and good recyclability with sustained efficiency, with its commercial viability impending.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144109177","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}
引用次数: 0
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