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Rhodium catalyzed sequential dual C-H annulation of 3-arylisoxazoles with 1,6-diynes to access fused naphthalenes. 铑催化3-芳基异恶唑与1,6-二炔序贯双碳氢环化反应得到熔融萘。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-23 DOI: 10.1039/d5ob00466g
Ramesh Kotipalli, T Mahipal Reddy, Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy
{"title":"Rhodium catalyzed sequential dual C-H annulation of 3-arylisoxazoles with 1,6-diynes to access fused naphthalenes.","authors":"Ramesh Kotipalli, T Mahipal Reddy, Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy","doi":"10.1039/d5ob00466g","DOIUrl":"https://doi.org/10.1039/d5ob00466g","url":null,"abstract":"<p><p>Selective dual C-H annulations with 1,<i>n</i>-diunsaturated systems represent a powerful tool for constructing multicyclic scaffolds in an expeditious manner. Here, we report a rhodium catalyzed sequential dual C-H annulation of 3-arylisoxazoles with 1,6-diynes for napthofused polycyclic systems. Some kinetic isotopic experiments were carried out to understand the reaction mechanism and some downstream experiments were conducted to demonstrate the potential of the methodology. The method features a broad substrate scope and scale-up capability.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144126113","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
Superacid-catalysed α-deuteration of ketones with D2O. 超强酸催化D2O对酮的α-氘化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-23 DOI: 10.1039/d5ob00683j
Haiying Yuan, Kaibo Xu, Jinling Li, Teck-Peng Loh, Zhenguo Zhang, Zhenhua Jia
{"title":"Superacid-catalysed α-deuteration of ketones with D<sub>2</sub>O.","authors":"Haiying Yuan, Kaibo Xu, Jinling Li, Teck-Peng Loh, Zhenguo Zhang, Zhenhua Jia","doi":"10.1039/d5ob00683j","DOIUrl":"https://doi.org/10.1039/d5ob00683j","url":null,"abstract":"<p><p>In this study, we present a superacid catalyzed protocol for the α-deuteration of ketones with D<sub>2</sub>O using [Ph<sub>3</sub>C]<sup>+</sup>[B(C<sub>6</sub>F<sub>5</sub>)<sub>4</sub>]<sup>-</sup> as a pre-catalyst to generate <i>in situ</i> the superacidic species [D]<sup>+</sup>[B(C<sub>6</sub>F<sub>5</sub>)<sub>4</sub>]<sup>-</sup>. The features of this catalytic process include simple manipulation, high deuteration efficiency (up to 99%), excellent functional group compatibility and a broad substrate scope, including 30 substrates comprising common building blocks and bioactive molecules like pentoxifylline. Moreover, the avoidance of toxic reagents enables sustainable access to deuterated products, demonstrating the method's practical potential for use in mechanistic studies and pharmaceutical applications.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144126115","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
Regioselective synthesis of α-(2-indolyl) ketones with arylaldehydes via a tandem reaction of 2-alkynylanilines. 2-炔基苯胺串联反应合成α-（2-吲哚基）酮与芳醛的区域选择性反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-23 DOI: 10.1039/d5ob00288e
Jianwei Wang, Qingxia Zhao, Hangxiao Fu, Jie Li
{"title":"Regioselective synthesis of α-(2-indolyl) ketones with arylaldehydes <i>via</i> a tandem reaction of 2-alkynylanilines.","authors":"Jianwei Wang, Qingxia Zhao, Hangxiao Fu, Jie Li","doi":"10.1039/d5ob00288e","DOIUrl":"https://doi.org/10.1039/d5ob00288e","url":null,"abstract":"<p><p>A base-promoted synthesis of α-(2-indolyl) ketones (or 2-(α-aryl benzyl ketone) indoles) is developed <i>via</i> 5-<i>endo-dig</i> cyclization of 2-alkynylanilines, followed by aroylation of the resulting carbanion. This transition metal-free reaction proceeded with high regioselectivity and a wide substrate scope (46 examples, up to 93% yield). Among the syntheses of 2-substituted indoles, this tandem process is straightforward and convenient.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144126111","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
Organocatalytic enantioselective α-difluoromethylketone thiolation of β-keto esters using phthalimide-SCF2COAr. 邻苯二胺- scf2coar有机催化β-酮酯的对映选择性α-二氟甲基酮硫代化。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-22 DOI: 10.1039/d5ob00520e
Wenning Chang, En Wang, Junqing Liang, Xusheng Shao, Xiaoyong Xu, Wu-Lin Yang, Zhong Li
{"title":"Organocatalytic enantioselective α-difluoromethylketone thiolation of β-keto esters using phthalimide-SCF<sub>2</sub>COAr.","authors":"Wenning Chang, En Wang, Junqing Liang, Xusheng Shao, Xiaoyong Xu, Wu-Lin Yang, Zhong Li","doi":"10.1039/d5ob00520e","DOIUrl":"https://doi.org/10.1039/d5ob00520e","url":null,"abstract":"<p><p>The first asymmetric α-difluoromethylketone thiolation of diverse β-keto esters using an electrophilic phthalimide-SCF<sub>2</sub>COAr reagent (PhthN-SCF<sub>2</sub>COAr) was reported. In the presence of cinchona-alkaloid-based catalyst (DHQD)<sub>2</sub>PHAL, the reaction was achieved in moderate yields with a moderate to excellent enantioselectivity (up to 93% ee) under mild reaction conditions and exhibited functional group compatibility. An ammonium hydrogen-bonded induction model was proposed to rationalize the origin of enantioselectivity.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144118380","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
Systematic investigation of the structure-property relationship of substituted p-alkoxy-azothiophenes. 取代对烷氧基偶氮噻吩构效关系的系统研究。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-22 DOI: 10.1039/d5ob00506j
Conrad Averdunk, Hermann A Wegner
{"title":"Systematic investigation of the structure-property relationship of substituted <i>p</i>-alkoxy-azothiophenes.","authors":"Conrad Averdunk, Hermann A Wegner","doi":"10.1039/d5ob00506j","DOIUrl":"https://doi.org/10.1039/d5ob00506j","url":null,"abstract":"<p><p>Differently substituted <i>p</i>-alkoxy azothiophenes with increasing alkoxy chains were systematically investigated in terms of their structure-property relationships. In particular, it was observed that increasing the length of the alkoxy chain had an unusual effect on the melting point, which did not follow the expected odd-even effect. It was also shown that changing the length of the alkoxy chain did not significantly affect the thermal half-life, a finding that disagrees with results reported in other studies. These observations provide valuable insights into structure-property relationships with important implications for the design and development of azobenzenes as molecular materials for various applications. Furthermore, each <i>p</i>-alkoxy azothiophene was investigated in terms of neat solid-state photoisomerisation or photoinduced liquefaction, which is a critical parameter for application as a molecular solar thermal phase-change (MOST-PCM) energy storage system.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144118382","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-triggered organophotoredox-catalyzed oxidation of 3-(benzylidine)indoline to indole-3-carbinols and 3-acyl indoles. 可见光触发的有机光氧化还原催化3-（苄基）吲哚氧化为吲哚-3-甲醇和3-酰基吲哚。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-21 DOI: 10.1039/d5ob00401b
Sourav Ghosh, Gopal Rana, Abhishek Kar, Rajkamal Sahoo, Umasish Jana
{"title":"Visible-light-triggered organophotoredox-catalyzed oxidation of 3-(benzylidine)indoline to indole-3-carbinols and 3-acyl indoles.","authors":"Sourav Ghosh, Gopal Rana, Abhishek Kar, Rajkamal Sahoo, Umasish Jana","doi":"10.1039/d5ob00401b","DOIUrl":"https://doi.org/10.1039/d5ob00401b","url":null,"abstract":"<p><p>A visible-light-triggered, Eosin-Y-catalyzed oxidative isomerization/carbon-oxygen bond formation of 3-(benzylidine) indolines has been explored to afford structurally diverse indole-3-carbinols and 3-acyl indoles in good-to-excellent yields. This new protocol is metal-free and features mild reaction conditions, easily available starting materials, and environmentally benign reaction conditions. A preliminary mechanistic study reveals that initially, an iminium ion-radical intermediate is formed <i>via</i> a single electron transfer (SET) mechanism, which facilitates cascade isomerization and C-O bond formation through the nucleophilic addition of H<sub>2</sub>O.</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":"144109180","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
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
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