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Catalyst-free aroylation of maleimides through Csp2-H functionalization with aldehydes and benzyl phenyl sulfides. 通过Csp2-H与醛和苯基硫化物的官能化，马来酰亚胺的无催化剂芳基化。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-07-28 DOI: 10.1039/d5ob00692a
Elmira Taheri, Farnaz Jafarpour
{"title":"Catalyst-free aroylation of maleimides through C<sub>sp<sup>2</sup></sub>-H functionalization with aldehydes and benzyl phenyl sulfides.","authors":"Elmira Taheri, Farnaz Jafarpour","doi":"10.1039/d5ob00692a","DOIUrl":"https://doi.org/10.1039/d5ob00692a","url":null,"abstract":"<p><p>Aroyl maleimides and their derivatives have potential applications as inhibitors, fluorophores, antibiotics, and anticonvulsants. The Friedel-Crafts method, as the renowned aroylation method of arenes and heteroarenes, is tedious and suffers from harsh conditions, incompatibility with electron-deficient substrates, and Lewis acid deactivation due to its coordination with the nitrogen of substrates. Hence, two eco-friendly and feasible metal-free di-<i>tert</i>-butyl peroxide-promoted methods are developed for the aroylation of maleimides toward 3,4-diaroyl maleimides and 3-amino-4-aroyl maleimides. These include the direct cross-dehydrogenative coupling of maleimides with aryl aldehydes and the tandem oxidative C-S cleavage/cross-dehydrogenative coupling of benzyl phenyl sulfides with maleimides. The results indicate the efficiency of the presented approaches with broad scopes.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144726138","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
Decarbonative routes to generate N-acyliminium ion intermediates for the synthesis of 3-substituted isoindolinones via an intermolecular amidoalkylation reaction. 通过分子间酰胺烷基化反应制备3-取代异吲哚酮用n -酰基铵离子中间体的脱碳路线。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-07-25 DOI: 10.1039/d5ob00687b
Nazir Uddin, Sudipta Roy, Santanab Giri, Gitish K Dutta, Paresh Nath Chatterjee
{"title":"Decarbonative routes to generate <i>N</i>-acyliminium ion intermediates for the synthesis of 3-substituted isoindolinones <i>via</i> an intermolecular amidoalkylation reaction.","authors":"Nazir Uddin, Sudipta Roy, Santanab Giri, Gitish K Dutta, Paresh Nath Chatterjee","doi":"10.1039/d5ob00687b","DOIUrl":"https://doi.org/10.1039/d5ob00687b","url":null,"abstract":"<p><p>An alternative and unique approach for synthesizing 3-substituted isoindolinones <i>via</i> Lewis acid-catalyzed C-C bond-breaking reactions has been reported. For this purpose, we successfully generated <i>N</i>-acyliminium ion intermediates from two different substrates [through (a) an FeCl<sub>3</sub> catalyzed C<sub>sp3</sub>-C<sub>sp2</sub> bond-breaking reaction in isoindolinones bearing electron-rich and sterically bulky aryl substituents at the 3-position and (b) a ZnCl<sub>2</sub> catalyzed C<sub>sp3</sub>-C<sub>sp3</sub> bond-breaking reaction in isoindolinones bearing 1,3-diketo substituents at the 3-position of the isoindolinone starting precursors], which were trapped by appropriate nucleophiles to produce more stable γ-substituted isoindolinones in good to excellent yields. The leaving ability of 1,3-diketones is higher than that of electron-rich and sterically bulky arenes in our developed method, which results in higher yields of γ-substituted isoindolinones from the starting precursor bearing the 1,3-diketo substituents at its 3-position. Theoretical investigations were also carried out to gain insight into the two different C-C bond-cleaving reactions.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144705831","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
Molecular aptamer beacon-based dual-mode exponential isothermal amplification for microRNA detection. 基于分子适体信标的双模指数等温扩增检测microRNA。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-07-25 DOI: 10.1039/d5ob00962f
Yu Han, Xuefeng Bian, Xiao Wang, Jiaying Chen, Liu Han, Xin Sun
{"title":"Molecular aptamer beacon-based dual-mode exponential isothermal amplification for microRNA detection.","authors":"Yu Han, Xuefeng Bian, Xiao Wang, Jiaying Chen, Liu Han, Xin Sun","doi":"10.1039/d5ob00962f","DOIUrl":"https://doi.org/10.1039/d5ob00962f","url":null,"abstract":"<p><p>Due to the limiting factors associated with microRNAs (miRNAs), including their low abundance, short sequence length, and high family sequence homology, the gold standard for miRNA detection does not meet the requirements for rapid and low-cost clinical detection of miRNAs in biological samples. To this end, we developed a one-pot method called molecular aptamer beacon-utilized exponential isothermal amplification (MABEXIA) for analyzing and detecting miRNAs. This novel devolved method was analyzed using both a fluorescent dye and a horseradish peroxidase (HRP) mediated chemiluminescence reaction with luminol and hydrogen peroxide for miRNA detection. The principle of the fluorescence platform involves hybridization of the target miRNA with MAB, which results in the formation of a large amount of double-stranded (ds) DNA products under the dual catalytic action of a DNA polymerase (Klenow Fragment) and nicking endonuclease (Nb.BbvCI) at a constant temperature. Moreover, this method exhibited good detection performance and was successfully applied to 1% human serum for miRNA detection. In contrast to the fluorescence method, the chemiluminescence approach achieved miRNA detection through the targeted interaction between the activated streptavidin (SA) aptamer within the dsDNA product and SA-coated magnetic beads. This method showed a good linear relationship in the ranges of 50 fM to 50 pM for miRNA detection. Finally, this chemiluminescence approach has a detection ability comparable to that of the gold standard for miRNA detection.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144705832","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 cascade cyclization of 2-isocyanoaryl thioethers/selenoethers: access to 2-arylthiobenzothiazoles/2-arylthiobenzoselenazoles. 可见光诱导的2-异氰芳基硫醚/硒醚级联环化：获得2-芳基硫代苯并噻唑/2-芳基硫代苯并硒唑。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-07-25 DOI: 10.1039/d5ob00869g
Dan Liu, Shichao Yang, Huanfeng Jiang, Wanqing Wu
{"title":"Visible light-induced cascade cyclization of 2-isocyanoaryl thioethers/selenoethers: access to 2-arylthiobenzothiazoles/2-arylthiobenzoselenazoles.","authors":"Dan Liu, Shichao Yang, Huanfeng Jiang, Wanqing Wu","doi":"10.1039/d5ob00869g","DOIUrl":"https://doi.org/10.1039/d5ob00869g","url":null,"abstract":"<p><p>Herein, we describe an efficient and atom-economical strategy for the synthesis of 2-arylthiobenzothiazole and 2-arylthiobenzoselenazole compounds <i>via</i> visible light-induced cascade cyclization of 2-isocyanoaryl thioethers/selenoethers with diaryl disulfides. Among them, two C-X (X = S, Se) bonds were formed under mild conditions in one single operation through thiyl radical addition to the isocyano groups of 2-isocyanoaryl thioethers/selenoethers followed by an annulation process. This protocol features excellent chemical selectivity, good functional group tolerance, simple operation and mild reaction conditions. Moreover, the derivatization reaction of the newly formed 2-arylthiobenzothiazole products demonstrates the utility of this method in organic synthesis.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144705748","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
Correction: NHC-catalysed synthesis of hydroxy methylene-bridged formyl-di-xylofuranose: access to tetrakis and spiro tricyclic xylofuranose. 更正：nhc催化合成羟基亚甲基桥接甲酰基二羟基呋喃糖：可得四环和螺三环羟基呋喃糖。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-07-24 DOI: 10.1039/d5ob90094h
Norein Sakander, Rahul Haldar, Debaraj Mukherjee
{"title":"Correction: NHC-catalysed synthesis of hydroxy methylene-bridged formyl-di-xylofuranose: access to tetrakis and spiro tricyclic xylofuranose.","authors":"Norein Sakander, Rahul Haldar, Debaraj Mukherjee","doi":"10.1039/d5ob90094h","DOIUrl":"https://doi.org/10.1039/d5ob90094h","url":null,"abstract":"<p><p>Correction for 'NHC-catalysed synthesis of hydroxy methylene-bridged formyl-di-xylofuranose: access to tetrakis and spiro tricyclic xylofuranose' by Norein Sakander <i>et al.</i>, <i>Org. Biomol. Chem.</i>, 2025, <b>23</b>, 3824-3829, https://doi.org/10.1039/D5OB00259A.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144697058","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
Recent advances in the synthesis of multiple helicenes. 多重螺旋烯合成的最新进展。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-07-24 DOI: 10.1039/d5ob00966a
Zhen Chen, Wei-Chen Guo, Chuan-Feng Chen
{"title":"Recent advances in the synthesis of multiple helicenes.","authors":"Zhen Chen, Wei-Chen Guo, Chuan-Feng Chen","doi":"10.1039/d5ob00966a","DOIUrl":"https://doi.org/10.1039/d5ob00966a","url":null,"abstract":"<p><p>Multiple helicenes, as helically twisted polycyclic frameworks with extended π-conjugated systems, have attracted growing attention due to their unique topologies, tunable chiroptical properties, and potential applications in chiral materials and organic electronics. In this review, we provide a systematic overview of the recent advances in the field of multiple helicenes and propose a concise classification strategy that classifies them into linear, cyclic, and cross-linked types. Based on this classification, we further summarize and highlight a range of efficient synthetic strategies that facilitate the construction of multiple helicenes. We hope this review will provide the design inspiration of multiple helicenes and further be helpful for the development of helicene chemistry.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144697155","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
Electrochemical [3 + 2] cycloaddition of anilines and enamine ketones: construction of 3-benzoylindole derivatives. 苯胺和烯胺酮的电化学[3 + 2]环加成：3-苯并酰吲哚衍生物的构建。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-07-24 DOI: 10.1039/d5ob00831j
Yangyang Hu, Chunlei Yu, Ya'nan Ran, Miao Yu, Jingwen Sun, Huiying Liu, Jiahui Zhang, Haijun Wang, Lei Liu
{"title":"Electrochemical [3 + 2] cycloaddition of anilines and enamine ketones: construction of 3-benzoylindole derivatives.","authors":"Yangyang Hu, Chunlei Yu, Ya'nan Ran, Miao Yu, Jingwen Sun, Huiying Liu, Jiahui Zhang, Haijun Wang, Lei Liu","doi":"10.1039/d5ob00831j","DOIUrl":"https://doi.org/10.1039/d5ob00831j","url":null,"abstract":"<p><p>This article describes an eco-friendly and atom-economical electrochemical protocol for the intermolecular [3 + 2] cycloaddition to synthesize 3-benzoylindole derivatives in synthetically viable yields. The oxidative cycloaddition proceeds under transition-metal-free and strong-oxidant-free conditions, generating H<sub>2</sub> and (Me)<sub>2</sub>NH as the byproducts, thereby aligning with green chemistry principles. Furthermore, the methodology exhibits exceptional synthetic versatility through successful late-stage diversification and compatibility with structurally diverse substrates. Preliminary cytotoxic evaluation <i>via</i> CCK-8 assays against two human carcinoma cell lines revealed potent bioactivity profiles, establishing a foundation for systematic exploration of indole-based pharmacophores. This protocol offers a sustainable alternative to conventional synthetic strategies while expanding the functionalization landscape of heteroaromatic systems.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144697072","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
Stereoinversion in Pd-catalyzed allylic substitution induced by modification of olefinic moiety in chiral phosphine-acrylamide ligands. 手性膦-丙烯酰胺配体中烯烃部分修饰引起的pd催化烯丙基取代的立体反转。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-07-24 DOI: 10.1039/d5ob01034a
Kohei Watanabe, Yuto Toba, Shimpei Mita, Yusuke Kanda, Toru Yagi, Kento Kanauchi, Manami Kumada, Yasushi Yoshida, Yoshio Kasashima, Ryo Takita, Masami Sakamoto, Takashi Mino
{"title":"Stereoinversion in Pd-catalyzed allylic substitution induced by modification of olefinic moiety in chiral phosphine-acrylamide ligands.","authors":"Kohei Watanabe, Yuto Toba, Shimpei Mita, Yusuke Kanda, Toru Yagi, Kento Kanauchi, Manami Kumada, Yasushi Yoshida, Yoshio Kasashima, Ryo Takita, Masami Sakamoto, Takashi Mino","doi":"10.1039/d5ob01034a","DOIUrl":"https://doi.org/10.1039/d5ob01034a","url":null,"abstract":"<p><p>We synthesized a series of phosphine-acrylamide chiral compounds 4 from chiral aminophosphine (<i>S</i>)-5 with various acyl chlorides and demonstrated that they can be used as chiral ligands in the Pd-catalyzed asymmetric allylic substitution reactions of allylic acetate with malonates or indoles. Although the ligands shared the same axial chirality, we found that the substitution pattern of the acrylamide led to an inversion in the stereoselectivity of the product and then investigated the underlying mechanism based on DFT calculations.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144697157","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
Site-selective C(sp3)-H amination of (het)aryl acetic acid derivatives under copper(II) catalysis. 铜（II）催化下芳基乙酸衍生物的位点选择性C(sp3)-H胺化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-07-24 DOI: 10.1039/d5ob00787a
Arun Kumar Hajra, Prasanjit Ghosh, Chandreyee Roy, Mrinalkanti Kundu, Sajal Das
{"title":"Site-selective C(sp<sup>3</sup>)-H amination of (het)aryl acetic acid derivatives under copper(II) catalysis.","authors":"Arun Kumar Hajra, Prasanjit Ghosh, Chandreyee Roy, Mrinalkanti Kundu, Sajal Das","doi":"10.1039/d5ob00787a","DOIUrl":"https://doi.org/10.1039/d5ob00787a","url":null,"abstract":"<p><p>A ubiquitous copper(II) catalyzed cross-dehydrogenative (CDC) process of (Het)arylacetamide derivatives employing free cyclic/acyclic secondary amines with the aid of 8-aminoimidazo[1,2-<i>a</i> pyridine] (8-AIP) as a bidentate chelating auxiliary has been successfully developed. This methodology exhibits a broad substrate scope with good functional group compatibility in the presence of air. Furthermore, the synthetic adaptability of this novel protocol is showcased through the post-diversification of synthesized derivatives.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144697156","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
A reaction-based fluorescence probe for selective detection of formaldehyde in food samples and its imaging application in living cells. 反应型荧光探针在食品中甲醛选择性检测及其在活细胞中的成像应用。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-07-23 DOI: 10.1039/d5ob00909j
Jieru Miao, Qiang Zhang, Zhuang Liu, Yan Lu
{"title":"A reaction-based fluorescence probe for selective detection of formaldehyde in food samples and its imaging application in living cells.","authors":"Jieru Miao, Qiang Zhang, Zhuang Liu, Yan Lu","doi":"10.1039/d5ob00909j","DOIUrl":"https://doi.org/10.1039/d5ob00909j","url":null,"abstract":"<p><p>Formaldehyde (FA) is a toxic pollutant that threatens both environmental and human health. Effective methods to detect FA in real-world samples and biological systems are urgently needed. Herein, we report the rational design and synthesis of NAPh-Lyso, a new lysosome-targetable reaction-based fluorescent probe for rapid and selective FA detection. NAPh-Lyso integrates three functional components, namely, a 1,8-naphthalimide fluorophore as the signaling unit, a hydrazine group as the specific FA-reactive site, and a morpholine moiety for subcellular localization. NAPh-Lyso operates through a distinctive Schiff base formation-coupled photoinduced electron transfer (PET) modulation mechanism, exhibiting a remarkable \"turn-on\" fluorescence response to FA in aqueous media with exceptional selectivity, rapid response kinetics (<2 min), and high sensitivity (LOD = 0.21 μM). It enables precise FA quantification in food (cabbage and mushrooms) and water samples (pond water and tap water), and lysosomal FA imaging in live cells. This work presents an advanced analytical platform for FA monitoring, while simultaneously offering valuable insights for the structural design of FA probes with broad applications in both analytical chemistry and biomedical research.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144688408","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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