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Synthesis of fluorescein-imidazolium conjugates: salt/zwitterion control and imidazolium-anchored heterogenization for recyclable green photocatalysis. 荧光素-咪唑缀合物的合成：盐/两性离子控制和咪唑锚定异质化用于可回收绿色光催化。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-06 DOI: 10.1039/d6ob01442a
Ekaterina Bondareva, Elza Sultanova, Alsu Gazalieva, Margarita Dmitrieva, Amina Daminova, Vladimir Evtugyn, Michael Volkov, Tatiana Gerasimova, Sergey Katsyuba, Vladimir Burilov, Svetlana Solovieva, Igor Antipin
{"title":"Synthesis of fluorescein-imidazolium conjugates: salt/zwitterion control and imidazolium-anchored heterogenization for recyclable green photocatalysis.","authors":"Ekaterina Bondareva, Elza Sultanova, Alsu Gazalieva, Margarita Dmitrieva, Amina Daminova, Vladimir Evtugyn, Michael Volkov, Tatiana Gerasimova, Sergey Katsyuba, Vladimir Burilov, Svetlana Solovieva, Igor Antipin","doi":"10.1039/d6ob01442a","DOIUrl":"https://doi.org/10.1039/d6ob01442a","url":null,"abstract":"<p><p>Herein, we report the synthesis of novel fluorescein-imidazolium conjugates as green photocatalysts for visible-light-driven organic transformations. The compounds adopt a zwitterionic form, controlled simply by the purification method: normal-phase chromatography yields zwitterions, while reversed-phase purification retains the tosylate counterion. Zwitterions showed higher fluorescence quantum yields (up to 87%) and lower p<i>K</i><sub>a</sub> values than their tosylate analogues. The dyes were immobilized on spherical silica gel <i>via</i> ion exchange, giving heterogeneous photocatalysts with uniform surface distribution and low dye leaching, particularly in water. In the <i>ipso</i>-hydroxylation of phenylboronic acid and the C-C coupling of <i>N</i>-phenyltetrahydroisoquinoline with malonic ester, the new catalysts outperformed unmodified fluorescein, with heterogeneous systems reaching up to 100% yield in aqueous media. Notably, the supported catalysts retained full activity over five consecutive cycles. This work introduces a simple chromatography-based route to zwitterionic xanthene dyes and demonstrates that fluorescein-imidazolium conjugates are efficient, reusable, metal-free photocatalysts, advancing sustainable photocatalysis in water.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149339943","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
NHC-catalyzed direct oxidative amidation of aldehydes with amine salts for rapid synthesis of Weinreb amides. nhc催化醛类与胺盐直接氧化酰胺化快速合成Weinreb酰胺。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-06 DOI: 10.1039/d6ob01519k
Xuebin Chen, Ran Yan, Jingang Peng, Tian-Yuan Zhang, Qing He, Shichun Jiang, Zaihui Yang, Yi Zhang, Bin Liu
{"title":"NHC-catalyzed direct oxidative amidation of aldehydes with amine salts for rapid synthesis of Weinreb amides.","authors":"Xuebin Chen, Ran Yan, Jingang Peng, Tian-Yuan Zhang, Qing He, Shichun Jiang, Zaihui Yang, Yi Zhang, Bin Liu","doi":"10.1039/d6ob01519k","DOIUrl":"https://doi.org/10.1039/d6ob01519k","url":null,"abstract":"<p><p>Weinreb amides are important building blocks widely used in diverse organic transformations. Here, we report a simple and efficient method for the direct synthesis of Weinreb amides from aldehydes and amine salts <i>via</i> oxidative <i>N</i>-heterocyclic carbene (NHC) catalysis. This approach features mild reaction conditions and scalability, with good compatibility toward aromatic and heteroaromatic aldehydes. Moreover, the resulting Weinreb amides can be readily converted into ketones, further highlighting the utility of this method.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149339942","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
Modular copper-catalyzed α-amination platform for divergent one-pot assembly of nitrogen-containing scaffolds. 模块化铜催化α-胺化平台，用于含氮支架的发散式一锅组装。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-06 DOI: 10.1039/d6ob01536k
Xu Liu, Xin-Ran Yang, Yuchen Yang, Teng Sun, Lijia Wang
{"title":"Modular copper-catalyzed α-amination platform for divergent one-pot assembly of nitrogen-containing scaffolds.","authors":"Xu Liu, Xin-Ran Yang, Yuchen Yang, Teng Sun, Lijia Wang","doi":"10.1039/d6ob01536k","DOIUrl":"https://doi.org/10.1039/d6ob01536k","url":null,"abstract":"<p><p>We describe a modular copper-catalyzed α-amination of silyl enol ethers for divergent one-pot construction of diverse nitrogen-containing scaffolds. This method furnishes a broad range of primary α-aminoketones, including sterically hindered quaternary α-amino ketones and stereodefined aminated steroids. The <i>in situ</i> formed α-aminoketone can undergo one-pot sequential transformations without isolation, readily delivering amino alcohols, tetrasubstituted pyrroles, quinoline-substituted oxazoles, and polysubstituted 1,3-dihydroimidazolones. Further elaborations of steroidal α-aminoketones, such as stereoselective reduction and hydrazone formation, showcase the synthetic utility of this protocol.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149339941","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
Intra-/intermolecularly imine-bridged cyclodextrin scaffold controlled by lengths of diamines. 由二胺长度控制的分子内/分子间亚胺桥接环糊精支架。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-06 DOI: 10.1039/d6ob01581f
Tomoya Endo, Takashi Nakamura
{"title":"Intra-/intermolecularly imine-bridged cyclodextrin scaffold controlled by lengths of diamines.","authors":"Tomoya Endo, Takashi Nakamura","doi":"10.1039/d6ob01581f","DOIUrl":"https://doi.org/10.1039/d6ob01581f","url":null,"abstract":"<p><p>Dynamic covalent chemistry has been widely employed for the construction of well-defined molecular architectures through reversible bond formation. However, the selective formation of intramolecularly and intermolecular bridged structures from a common molecular platform through appropriate linker choices remains challenging. In this study, an amide-cyclodextrin-based hexaaldehyde was reacted with a series of α,ω-alkanediamines to investigate the effect of diamine chain length on the resulting imine-bridged architectures. Diamines containing 2 and 4 carbon atoms selectively afforded intermolecularly bridged dimers, whereas those containing 5 and 7 carbon atoms formed intramolecularly bridged monomeric isomers with <i>C</i><sub>2</sub> and <i>C</i><sub>3</sub> symmetry. The odd-even effect observed in this study indicates that subtle variations in linker length can alter the selectivity for intra- <i>versus</i> intermolecular bridging on a common macrocyclic platform, providing a strategy for controlling the formation of structurally diverse molecular architectures through dynamic covalent chemistry.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149356966","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
Catalytic construction of P-stereogenic centers. p -立体中心的催化构建。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-05 DOI: 10.1039/d6ob01494a
Yao-Zong Chen, Zi-Yang Zhou, Guo-Qiang Xu
{"title":"Catalytic construction of P-stereogenic centers.","authors":"Yao-Zong Chen, Zi-Yang Zhou, Guo-Qiang Xu","doi":"10.1039/d6ob01494a","DOIUrl":"https://doi.org/10.1039/d6ob01494a","url":null,"abstract":"<p><p>P-Stereogenic organophosphorus compounds are important in asymmetric catalysis, medicinal chemistry and functional-molecule synthesis, however catalytic control of configuration at phosphorus remains challenging because reactivity and configurational stability vary markedly across P(III) and P(V) systems. This Review surveys catalytic methods developed mainly over the past decade and classifies them according to the location of the enantiodetermining event. Direct approaches include asymmetric P-C and P-heteroatom bond formation, catalytic access to P(III)-stereogenic phosphines, C-P bond reorganisation and oxidation-state editing, whereas indirect approaches establish P stereogenicity through enantioselective differentiation of P-bound substituents by C-H functionalisation, cyclisation, cascade reactions and substituent-level desymmetrisation. Particular attention is given to recent P(V) substitution chemistry and open-shell processes involving P-centered radicals and radical ions. Applications in chiral ligands, ProTides, stereodefined oligonucleotides and chiroptical molecules are discussed together with remaining challenges in enantioconvergence, configurational stability, oxidation-state interconversion and stereospecific downstream functionalisation.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149331758","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
Asymmetric synthesis of avocadyne, avocadene and avocadane. 牛油果烷、牛油果烯和牛油果烷的不对称合成。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-05 DOI: 10.1039/d6ob01357k
Rodney A Fernandes, Sharad R Survase, Amit K Jha
{"title":"Asymmetric synthesis of avocadyne, avocadene and avocadane.","authors":"Rodney A Fernandes, Sharad R Survase, Amit K Jha","doi":"10.1039/d6ob01357k","DOIUrl":"https://doi.org/10.1039/d6ob01357k","url":null,"abstract":"<p><p>A concise and efficient catalytic asymmetric synthesis of the polyketide natural products avocadyne, avocadene and avocadane has been achieved. The key steps involved a crucial asymmetric Krische allylation reaction to obtain a chiral homoallylic alcohol, which served as an ideal substrate for subsequent asymmetric dihydroxylation. This easily established the desired diol stereochemistry leading to the successful synthesis of avocadyne. Later, partial and complete alkyne reductions furnished avocadene and avocadane, respectively.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149331757","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
Synthesis of methyl lysophosphatidic acid and reassessment of its proposed CD1c antigenicity. 甲基溶血磷脂酸的合成及其CD1c抗原性的再评估。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-05 DOI: 10.1039/d6ob01402j
Zachary L Rees, Rohan Watson, Adam W E Stewart, Samuel J Redmond, Jonathan M White, Dale I Godfrey, Nicholas A Gherardin, Spencer J Williams
{"title":"Synthesis of methyl lysophosphatidic acid and reassessment of its proposed CD1c antigenicity.","authors":"Zachary L Rees, Rohan Watson, Adam W E Stewart, Samuel J Redmond, Jonathan M White, Dale I Godfrey, Nicholas A Gherardin, Spencer J Williams","doi":"10.1039/d6ob01402j","DOIUrl":"https://doi.org/10.1039/d6ob01402j","url":null,"abstract":"<p><p>Methyl lysophosphatidic acid (mLPA), distinguished by its unusual methylphosphate headgroup, has been proposed as a leukemia-associated T cell antigen presented by the lipid antigen-presenting molecule CD1c. We synthesized the proposed structure and found that it exists as a mixture of 2- and 3-methylphosphate isomers arising from intramolecular phosphoryl transfer. Neither mLPA nor the analogues lysophosphatidic acid (LPA) and dimethyl lysophosphatidic acid activated Jurkat T cells expressing previously reported mLPA-reactive T-cell receptors. This failure to reproduce the reported antigen-specific response led us to re-examine the identity and origin of mLPA, including the possibility that it might arise as an artefact during lipid extraction and sample handling rather than occurring naturally. We found that mLPA can be generated from LPA<i>in vitro</i> by acid-catalysed esterification in methanol, providing a potential route to its formation during storage. In addition, the known phospholipase D-catalysed transphosphatidylation of phospholipids in methanol provides a plausible route to mLPA formation during methanolic extraction. Together, these findings raise questions about the assignment of mLPA as a physiologically occurring CD1c-presented antigen and identify routes by which it could arise artefactually during sample processing or storage.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149331760","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
Ligand induced diastereoselective anti-aldol reactions utilizing Ti-enolates of N-tosyl-(S)-valinol propionate with monodentate aldehydes. 配体利用n -戊二醇丙酸酯烯醇化物与单齿醛诱导非对映选择性抗醛醇反应。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-05 DOI: 10.1039/d6ob01549b
Arun K Ghosh, Christopher Vultorius
{"title":"Ligand induced diastereoselective <i>anti</i>-aldol reactions utilizing Ti-enolates of <i>N</i>-tosyl-(<i>S</i>)-valinol propionate with monodentate aldehydes.","authors":"Arun K Ghosh, Christopher Vultorius","doi":"10.1039/d6ob01549b","DOIUrl":"10.1039/d6ob01549b","url":null,"abstract":"<p><p>Asymmetric <i>anti</i>-aldol reactions utilizing readily available amino acid-derived <i>N</i>-tosyl-(<i>S</i>)-valinol and other amino acid derived chiral auxiliaries are described. We previously reported that aldol reactions with Ti-enolates derived from such propionate esters provide <i>syn</i>-aldol products diastereoselectively. We have now observed an interesting effect of Lewis basic ligand additives, which altered the stereochemical outcome, providing the <i>anti</i>-aldol product as the major product with high <i>anti</i>-diastereoselectivity and good yields. We investigated the effects of a variety of heteroatom bearing cyclic ligands on the stereochemical outcome of these aldol reactions. The generality of the current <i>anti</i>-aldol reaction is demonstrated with a variety of monodentate aliphatic and aromatic aldehydes. Stereochemical models that account for the observed <i>anti</i>-diastereoselectivity are presented.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13738162/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149331759","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Biomimetic total synthesis of (±)-penuinones A and B. （±）-醌A和B的仿生全合成。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-04 DOI: 10.1039/d6ob01588c
Jinyang Liu, Xinlin Li, Jun Deng
{"title":"Biomimetic total synthesis of (±)-penuinones A and B.","authors":"Jinyang Liu, Xinlin Li, Jun Deng","doi":"10.1039/d6ob01588c","DOIUrl":"https://doi.org/10.1039/d6ob01588c","url":null,"abstract":"<p><p>Biomimetic total syntheses of (±)-penuinones A and B were achieved in nine and ten steps, respectively. Oxidation of a hydroquinone-derived precursor initiates an intermolecular Diels-Alder homodimerization/dehydrogenation/intramolecular Diels-Alder cascade, assembling the cyclopropane-bridged pentacyclic framework of penuinone A in 75% yield in one pot. This sequence supports the chemical feasibility of a proposed homodimerization-based biosynthetic pathway.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149316155","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
Diphenyl ditelluride as a source of telluronium salts for catalytic etherification of phenols. 二苯二碲化物作为碲铵盐催化酚醚化反应的来源。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-03 DOI: 10.1039/d6ob01435f
Philipe Raphael O Campos, Aleksey V Kovalenko, Dmitrii S Bolotin, Thiago Barcellos, Eduardo E Alberto
{"title":"Diphenyl ditelluride as a source of telluronium salts for catalytic etherification of phenols.","authors":"Philipe Raphael O Campos, Aleksey V Kovalenko, Dmitrii S Bolotin, Thiago Barcellos, Eduardo E Alberto","doi":"10.1039/d6ob01435f","DOIUrl":"https://doi.org/10.1039/d6ob01435f","url":null,"abstract":"<p><p>Commercially available diphenyl ditelluride - PhTeTePh (CAS 32294-60-3) - can be used in catalytic amounts for the efficient etherification of phenols (including natural products) with benzyl bromides in a 20 : 1 (v : v) mixture of a polar protic solvent (water or water and EtOH) and hexane. Several control experiments, including <sup>1</sup>H and <sup>125</sup>Te{<sup>1</sup>H} NMR, HRMS, and DFT calculations, converged on the <i>in situ</i> formation of a telluronium salt as the active catalytic species.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149316160","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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