European Journal of Organic Chemistry最新文献_第6页

Design, Synthesis and Characterization of BODIPY based 1H‐Tetrazole Ligands 基于 BODIPY 的 1H-Tetrazole 配体的设计、合成和表征

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202401239

Martin Huber , Matthias Schöbinger , Jordi Cirera , Berthold Stöger , Peter Weinberger

{"title":"Design, Synthesis and Characterization of BODIPY based 1H‐Tetrazole Ligands","authors":"Martin Huber , Matthias Schöbinger , Jordi Cirera , Berthold Stöger , Peter Weinberger","doi":"10.1002/ejoc.202401239","DOIUrl":"10.1002/ejoc.202401239","url":null,"abstract":"<div><div>Four novel fluorescence active ligands (1–4) consisting of a 1H‐tetrazol‐1‐yl moiety as coordinating unit and a 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) derivative as fluorophore, bridged via alkyl (‐(CH2)n‐, n=1–3) or benzyl (‐CH2‐C6H4‐) spacers were designed. Successful synthesis is demonstrated by multinuclear NMR spectroscopy, as well as powder and single crystal XRD analysis. The methylene bridged ligand 2 (4,4‐difluoro‐1,3,5,7‐tetramethyl‐8‐[(1H‐tetrazol‐1‐yl)methyl]‐4‐bora‐3a,4a‐diaza‐s‐indacene) crystallizes in different polymorphs and solvatomorphs, in contrast to the other three ligands, which show no polymorphism under identical conditions. Photophysical studies revealed high fluorescence quantum yields (69 – 95 %) in solution for the ‐(CH2)2‐ bridged ligand 3 (4,4‐difluoro‐1,3,5,7‐tetramethyl‐8‐[(1H‐tetrazol‐1‐yl)ethyl]‐4‐bora‐3a,4a‐diaza‐s‐indacene) and the ‐(CH2)3‐ bridged ligand 4 (4,4‐difluoro‐1,3,5,7‐tetramethyl‐8‐[(1H‐tetrazol‐1‐yl)propyl]‐4‐bora‐3a,4a‐diaza‐s‐indacene). Non‐radiative decay due to rotational motion of the 1H‐tetrazol‐1‐yl‐ and/or ‐CH2‐C6H4‐ moiety for 2 and 1 (4,4‐difluoro‐1,3,5,7‐tetramethyl‐8‐[4‐((1H‐tetrazol‐1‐yl)methyl)phenyl]‐4‐bora‐3a,4a‐diaza‐s‐indacene) respectively leads to reduced quantum yields of ≥35 %. Complete fluorescence quenching upon aggregation is prevented by installation of the sterically demanding 1H‐tetrazol‐1‐yl moiety and a spacer in meso‐position of the BODIPY core to elongate the intermolecular distances between two adjacent BODIPY cores. Detailed photophysical and crystallographic investigations are supported by theoretical calculations.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 7","pages":"Article e202401239"},"PeriodicalIF":2.5,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202401239","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142600045","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

Photoinduced DNA Cleavage Using Bioinspired Photostable Flavin Analogues 使用生物启发的光稳定黄素类似物进行光诱导 DNA 切割

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202401001

Dipayan Mondal , Ashutosh Kumar Mishra

引用次数: 0

Aryl Radicals Generated from Aryl Pinacol Boronates Modify Peptides and Proteins 芳基频哪醇硼酸酯产生的芳基自由基可修饰肽和蛋白质

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202401246

Haoyu Chen , Dongqing Wu , Julian Holzinger , Rainer Götz , Dorian Didier , Anne K. Schütz , Sabine Schneider , Pavel Kielkowski

{"title":"Aryl Radicals Generated from Aryl Pinacol Boronates Modify Peptides and Proteins","authors":"Haoyu Chen , Dongqing Wu , Julian Holzinger , Rainer Götz , Dorian Didier , Anne K. Schütz , Sabine Schneider , Pavel Kielkowski","doi":"10.1002/ejoc.202401246","DOIUrl":"10.1002/ejoc.202401246","url":null,"abstract":"<div><div>We report here a distinct reaction, which generates aryl radicals from aryl pinacol boronates under mild aqueous conditions and can be used for peptide and protein modifications. The strategy leverages the versatile reactivity of aryl pinacol boronates to form aryl radicals in presence of ammonium persulfate (APS). The formed aryl radicals insert readily into peptide disulfide bonds while tolerating other functionalities. On the protein level, the reactivity extends beyond the disulfide bonds. The methodology benefits from the accessibility of starting aryl pinacol boronates, as well as biocompatible conditions. In contrast to conventional methods used for aryl radical generation, the strategy is metal‐free, does not require photoinduction and can be readily performed under aqueous conditions. The mechanism of the reactions was investigated by radical‐trapping experiments, spectroscopic analysis and oxygen scavenging. The presented approach broadens the application of aryl pinacol boronate esters in radical reactions.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 7","pages":"Article e202401246"},"PeriodicalIF":2.5,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202401246","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142596777","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

Front Cover: p-Anisil as a Versatile Catalyst for the E-to-Z Photoisomerization of Activated Alkenes - Application in Late-Stage Modification of Small Molecule Drugs, Di- and Tripeptides (Eur. J. Org. Chem. 7/2025)

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202580701

Thanh V. Q. Nguyen, Peter R. Hansen

{"title":"Front Cover: p-Anisil as a Versatile Catalyst for the E-to-Z Photoisomerization of Activated Alkenes - Application in Late-Stage Modification of Small Molecule Drugs, Di- and Tripeptides (Eur. J. Org. Chem. 7/2025)","authors":"Thanh V. Q. Nguyen, Peter R. Hansen","doi":"10.1002/ejoc.202580701","DOIUrl":"https://doi.org/10.1002/ejoc.202580701","url":null,"abstract":"The Front Cover illustrates expedient access to complex Z-alkenes from drugs and oligopeptides through a two-step synthetic sequence: a metal-catalyzed, directed C−H bond olefination followed by an E-to-Z photoisomerization under blue light. While the former step is established in the literature, the latter requires the development of a highly effective and robust photocatalytic system. Key to the success is the discovery of p-anisil as a versatile photocatalyst that is able to convert E-alkenes to their Z-isomers with Z/E up to >99:1. During the course of this work, 11 Z-alkenes were successfully synthesized from five drugs and two oligopeptides, thus demonstrating the practicability of the concept. More information can be found in the Research Article by T. V. Q. Nguyen and P. R. Hansen (DOI: 10.1002/ejoc.202401338). Cover by T.V.Q.N. (AstraZeneca) and Dr. Binh Phan (Essity).\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture>\u0000 </div>\u0000 </figure>\u0000 ","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 7","pages":""},"PeriodicalIF":2.5,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202580701","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143431520","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

Electrochemical Alkoxylation of Benzylic C(sp3)−H Bonds 苯基C(sp3)−H键的电化学烷氧化反应

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202401227

Naixuan Zhao , Geyao Xie , Miao Zheng , Shunzhen Chang , Zhenwei Zhang , Guoxue He , Yu Zhou

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Ring Opening and C(ω)‐S Coupling: Nickel‐Mediated Transformation of Alicyclic Alkoxyhydroperoxides 开环和C(ω)-S偶联：镍介导的脂环烷氧氢过氧化物转化

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202401198

Dmitri I. Fomenkov , Roman A. Budekhin , Olga M. Mulina , Olga A. Komarova , Mikhail M. Doronin , Yulia Yu. Belyakova , Liang‐Nian He , Ivan A. Yaremenko , Alexander O. Terent'ev

引用次数: 0

A Meta‐Analysis of Published Brønsted Plots Supports Brønsted's “Conventional” pKa Values: 14.00 for Water and 0.00 for H+(aq)

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202401135

Todd P. Silverstein, Thomas Neils

{"title":"A Meta‐Analysis of Published Brønsted Plots Supports Brønsted's “Conventional” pKa Values: 14.00 for Water and 0.00 for H+(aq)","authors":"Todd P. Silverstein, Thomas Neils","doi":"10.1002/ejoc.202401135","DOIUrl":"https://doi.org/10.1002/ejoc.202401135","url":null,"abstract":"In the early 1900s, Brønsted used two different pairs of pKa values for water and the aqueous proton: He denoted 14.00 and 0.00 (respectively) as the “conventional” values, and 15.74 and −1.74 (respectively) as the “rational” values. Although the conventional values have been supported by both experiment and theory, the rational values have been employed in the vast majority of studies involving Brønsted plots up to the present day. Here we present a meta‐analysis of 67 Brønsted plots published from 1924 to 2010, revealing that rational pKa’ values more frequently appear as statistical outliers (a greater than 80 % rejection rate) compared to conventional values (a roughly 50 % rejection rate) based on Q‐tests. Furthermore, in 85 % of examined plots, the conventional points align more closely with best‐fit lines. An evaluation of Hupe and Pohl's Marcus plots also shows a somewhat better fit with the conventional rather than the rational pKa’ values. Finally, in the bond length versus pKa investigations published by Brydon et al., all the rational points were statistically rejected, whereas the conventional values were accepted. From our statistical analyses, we conclude that a convincing majority of experimental evidence from published Brønsted plots leads one to question the validity of Brønsted's rational pKa’ values for water and the aqueous proton (15.74 and −1.74, respectively).","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"12 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143435381","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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Greening the Synthesis of 2,3‐Dihydrobenzofuran Selenides: I2/TBHP‐Promoted Selenocyclization of 2‐Allylphenols 2,3‐二氢苯并呋喃硒化物的合成：I2/TBHP‐促进2‐烯丙基酚的硒环化

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202401243

Ricardo H. Bartz , Pedro S. Souza , Lucas E. B. Iarocz , Paola S. Hellwig , Prof. Raquel G. Jacob , Prof. Márcio S. Silva , Prof. Eder J. Lenardão , Prof. Gelson Perin

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Synthesis of 4‐Iodoimidazole Nucleosides: A Biocatalyzed Whole Cell Approach

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202400950

Lautaro A. M. Giaimo , Dr. Leticia Lafuente , Dr. Romina N. Fernández Varela , Dr. Matías L. Nóbile , Dr. Adolfo M. Iribarren , Dr. Elizabeth S. Lewkowicz

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Efficient Synthesis of Indolyl Benzo[b]carbazoles via Surfactant-Type Brønsted Acid-Catalyzed Three-Component Cyclization of Ortho-Formylarylketones with Indoles

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202401466

Jun Yang, Tianxing Li, Hui Jin, Lixin Zhang

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