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Study of tribenzo[b,d,f]azepine as donor in D-A photocatalysts. 三苯并[b，d，f]氮平作d - a光催化剂的研究。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-05-14 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.76
Katy Medrano-Uribe, Jorge Humbrías-Martín, Luca Dell'Amico
{"title":"Study of tribenzo[<i>b</i>,<i>d</i>,<i>f</i>]azepine as donor in D-A photocatalysts.","authors":"Katy Medrano-Uribe, Jorge Humbrías-Martín, Luca Dell'Amico","doi":"10.3762/bjoc.21.76","DOIUrl":"10.3762/bjoc.21.76","url":null,"abstract":"<p><p>Since the discovery of donor-acceptor (D-A) type molecules in the field of materials science, they have found great applicability in the field of photocatalysis. Most of these compounds are based on complex D-A-D structures or multi-D-A systems, such as 4CzIPN. Whereas these systems have been widely studied and applied as photocatalysts, simpler D-A structures remain less explored. Nevertheless, the simplicity of D-A structures makes them the ideal structures to further understand the structure-property relationship of D-A molecules for optimizing their photocatalytic performance by simpler modification of the different D-A subunits. In particular, D-A structures featuring sulfur-based acceptors and nitrogen donors have gained increasing attention for their use as photoredox catalysts. This study introduces a new family of D-A molecules by exploring various sulfur-based acceptors and nitrogen donors, including a novel tribenzo[<i>b,d,f</i>]azepine (TBA) unit and 5<i>H</i>-dibenz[<i>b,f</i>]azepine (IMD). Our findings demonstrate that these simple D-A structures exhibit promising photocatalytic properties, comparable to those of more complex D-A-D systems.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"935-944"},"PeriodicalIF":2.2,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12117207/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144172589","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
A convergent synthetic approach to the tetracyclic core framework of khayanolide-type limonoids. khayanolide型柠檬素四环核心骨架的收敛合成方法。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-05-12 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.75
Zhiyang Zhang, Jialei Hu, Hanfeng Ding, Li Zhang, Peirong Rao
{"title":"A convergent synthetic approach to the tetracyclic core framework of khayanolide-type limonoids.","authors":"Zhiyang Zhang, Jialei Hu, Hanfeng Ding, Li Zhang, Peirong Rao","doi":"10.3762/bjoc.21.75","DOIUrl":"10.3762/bjoc.21.75","url":null,"abstract":"<p><p>A convergent approach for the enantioselective construction of an advanced intermediate containing the [5,5,6,6]-tetracyclic core framework of the khayanolide-type limonoids was described. The strategy features an acylative kinetic resolution of the benzylic alcohol, a 1,2-Grignard addition and an AcOH-interrupted Nazarov cyclization.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"926-934"},"PeriodicalIF":2.2,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12117208/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144172581","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Silver(I) triflate-catalyzed post-Ugi synthesis of pyrazolodiazepines. 三氟化银催化后ugi合成吡唑二氮卓类药物。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-05-08 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.74
Muhammad Hasan, Anatoly A Peshkov, Syed Anis Ali Shah, Andrey Belyaev, Chang-Keun Lim, Shunyi Wang, Vsevolod A Peshkov
{"title":"Silver(I) triflate-catalyzed post-Ugi synthesis of pyrazolodiazepines.","authors":"Muhammad Hasan, Anatoly A Peshkov, Syed Anis Ali Shah, Andrey Belyaev, Chang-Keun Lim, Shunyi Wang, Vsevolod A Peshkov","doi":"10.3762/bjoc.21.74","DOIUrl":"https://doi.org/10.3762/bjoc.21.74","url":null,"abstract":"<p><p>A silver(I) triflate-catalyzed post-Ugi assembly of novel pyrazolo[1,5-<i>a</i>][1,4]diazepine scaffolds is reported offering high yields (up to 98%) under mild conditions. The synthetic sequence involves the Ugi four-component reaction (U4CR) of pyrazole-3-carbaldehydes, primary amines, 3-substituted propiolic acids, and isocyanides, followed by a silver(I) triflate-catalyzed intramolecular heteroannulation of the resulting pyrazole-tethered propargylamides occurring in a 7-<i>endo</i>-<i>dig</i> fashion. The approach is scalable and tolerates a diverse range of substitution patterns.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"915-925"},"PeriodicalIF":2.2,"publicationDate":"2025-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12067096/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143963940","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Recent advances in controllable/divergent synthesis. 可控/发散合成的最新进展。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-05-07 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.73
Jilei Cao, Leiyang Bai, Xuefeng Jiang
{"title":"Recent advances in controllable/divergent synthesis.","authors":"Jilei Cao, Leiyang Bai, Xuefeng Jiang","doi":"10.3762/bjoc.21.73","DOIUrl":"https://doi.org/10.3762/bjoc.21.73","url":null,"abstract":"<p><p>The development of streamlined methodologies for the expeditious assembly of structurally diverse organic architectures represents a paramount objective in contemporary synthetic chemistry, with far-reaching implications across pharmaceutical development, advanced materials innovation, and fundamental molecular science research. In recent years, controllable/divergent synthetic strategies for organic functional molecules using common starting materials have garnered significant attention due to their high efficiency. This review categorizes recent literatures focusing on key regulatory factors for product divergent formation, in which controlling chemical selectivity primarily relies on ligands, metal catalysts, solvents, time, temperature, acids/bases, and subtle modifications of substrates. To gain a deeper understanding of the mechanisms underlying reaction activity and selectivity differentiation, the review provides a systematic analysis of the mechanisms of critical steps through specific case studies. It is hoped that the controllable/divergent synthesis concept will spark the interest of practitioners and aficionados to delve deeper into the discipline and pursue novel advancements in the realm of chemical synthesis.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"890-914"},"PeriodicalIF":2.2,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12067097/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143961175","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion-π interactions. 基于氢键和阴离子π相互作用的超环宿主二羧酸盐识别。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-05-06 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.72
Wen-Hui Mi, Teng-Yu Huang, Xu-Dong Wang, Yu-Fei Ao, Qi-Qiang Wang, De-Xian Wang
{"title":"Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion-π interactions.","authors":"Wen-Hui Mi, Teng-Yu Huang, Xu-Dong Wang, Yu-Fei Ao, Qi-Qiang Wang, De-Xian Wang","doi":"10.3762/bjoc.21.72","DOIUrl":"https://doi.org/10.3762/bjoc.21.72","url":null,"abstract":"<p><p>The efficient binding of dicarboxylates represents an important yet challenging issue in supramolecular chemistry. In this study, we designed functional ultracycles as hosts to accommodate large organic dicarboxylate anions. These ultracycles were synthesized via a one-pot strategy starting from macrocyclic precursors. Host-dicarboxylate binding was investigated using <sup>1</sup>H NMR titrations, revealing that <b>B4aH</b> exhibits strong binding affinities toward a series of dicarboxylates, with association constants reaching up to 6896 M<sup>-1</sup>. The selectivity for heptanedioate (<b>C7</b> <b><sup>2-</sup></b> ) was attributed to cooperative hydrogen bonding, anion-π interactions, and a size-matching effect, as supported by DFT optimizations.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"884-889"},"PeriodicalIF":2.2,"publicationDate":"2025-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12067094/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143958310","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Cu-Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes. cu - bpin介导的4,4-二氯-2-丁烯酸衍生物二聚化反应可以合成密集功能化的环丙烷。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-05-05 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.71
Patricia Gómez-Roibás, Andrea Chaves-Pouso, Martín Fañanás-Mastral
{"title":"Cu-Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes.","authors":"Patricia Gómez-Roibás, Andrea Chaves-Pouso, Martín Fañanás-Mastral","doi":"10.3762/bjoc.21.71","DOIUrl":"https://doi.org/10.3762/bjoc.21.71","url":null,"abstract":"<p><p>4,4-Dichloro-2-butenoic acid derivatives are shown to undergo a rare dimerization process when reacted with bis(pinacolato)diboron under copper catalysis. The reaction provides densely functionalized products with excellent levels of chemo-, regio-, and diastereoselectivity. This high degree of functionalization makes these products versatile building blocks for the stereoselective synthesis of chlorocyclopropanes.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"877-883"},"PeriodicalIF":2.2,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12067098/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143962402","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Data accessibility in the chemical sciences: an analysis of recent practice in organic chemistry journals. 化学科学中的数据可及性：有机化学期刊近期实践分析。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-05-02 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.70
Sally Bloodworth, Cerys Willoughby, Simon J Coles
{"title":"Data accessibility in the chemical sciences: an analysis of recent practice in organic chemistry journals.","authors":"Sally Bloodworth, Cerys Willoughby, Simon J Coles","doi":"10.3762/bjoc.21.70","DOIUrl":"https://doi.org/10.3762/bjoc.21.70","url":null,"abstract":"<p><p>The discoverability and reusability of data is critical for machine learning to drive new discovery in the chemical sciences, and the 'FAIR Guiding Principles for scientific data management and stewardship' provide a measurable set of guidelines that can be used to ensure the accessibility of reusable data. We investigate the data practice of researchers publishing in specialist organic chemistry journals, by analyzing the outputs of 240 randomly selected research papers from 12 top-ranked journals published in early 2023. We investigate compliance with recommended (but not compulsory) data policies, assess the accessibility and reusability of data, and if the existence of specific recommendations for publishing NMR data by some journals supports author compliance. We find that, although authors meet mandated requirements, there is very limited compliance with data sharing policies that are only recommended by journals. Overall, there is little evidence to suggest that authors' publishing practice meets FAIR data guidance. We suggest first steps that researchers can take to move towards a positive culture of data sharing in organic chemistry. Routine actions that we encourage as standard practice include deposition of raw and metadata to open repositories, and inclusion of machine-readable structure identifiers for all reported compounds.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"864-876"},"PeriodicalIF":2.2,"publicationDate":"2025-05-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12051459/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143961124","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Light-enabled intramolecular [2 + 2] cycloaddition via photoactivation of simple alkenylboronic esters. 通过光激活简单烯基硼酯的分子内[2 + 2]环加成。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-04-30 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.69
Lewis McGhie, Hannah M Kortman, Jenna Rumpf, Peter H Seeberger, John J Molloy
{"title":"Light-enabled intramolecular [2 + 2] cycloaddition via photoactivation of simple alkenylboronic esters.","authors":"Lewis McGhie, Hannah M Kortman, Jenna Rumpf, Peter H Seeberger, John J Molloy","doi":"10.3762/bjoc.21.69","DOIUrl":"https://doi.org/10.3762/bjoc.21.69","url":null,"abstract":"<p><p>The photoactivation of organic molecules via energy transfer (EnT) catalysis is often limited to conjugated systems that have low-energy triplet excited states, with simple alkenes remaining an intractable challenge. The ability to address this limitation, using high energy sensitizers, would represent an attractive platform for future reaction design. Here, we disclose the photoactivation of simple alkenylboronic esters established using alkene scrambling as a rapid reaction probe to identify a suitable catalyst and boron motif. Cyclic voltammetry, UV-vis analysis, and control reactions support sensitization, enabling an intramolecular [2 + 2] cycloaddition to be realized accessing 3D bicyclic fragments containing a boron handle.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"854-863"},"PeriodicalIF":2.2,"publicationDate":"2025-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12051466/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143963312","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Unraveling cooperative interactions between complexed ions in dual-host strategy for cesium salt separation. 双宿主分离铯盐策略中络合离子间的协同相互作用。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-04-29 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.68
Zhihua Liu, Ya-Zhi Chen, Ji Wang, Qingling Nie, Wei Zhao, Biao Wu
{"title":"Unraveling cooperative interactions between complexed ions in dual-host strategy for cesium salt separation.","authors":"Zhihua Liu, Ya-Zhi Chen, Ji Wang, Qingling Nie, Wei Zhao, Biao Wu","doi":"10.3762/bjoc.21.68","DOIUrl":"https://doi.org/10.3762/bjoc.21.68","url":null,"abstract":"<p><p>The dual-host strategy offers a straightforward approach to ion separation, yet the nature of cooperative interactions between receptor-complexed cations and anions remains poorly understood. In this study, we utilize 18-crown-6 as a cation receptor and a tripodal hexaurea receptor <b>L</b> as an anion receptor to extract cesium salts (chloride, nitrate, carbonate, sulfate, and phosphate) from the solid phase into chloroform. Remarkably, Cs<sub>3</sub>PO<sub>4</sub> exhibits the highest extraction efficiency, driven by strong cooperative interactions involving ion-dipole coordination between Cs<sup>+</sup> and carbonyl (C=O) groups, as well as direct ion-pairing interactions between 18-crown-6-complexed Cs<sup>+</sup> and hexaurea-bound PO<sub>4</sub> <sup>3-</sup>. Single-crystal structural analysis corroborates these interactions, shedding light on the underlying mechanisms and providing valuable guidance for the rational design of advanced dual-host systems for selective ion separation.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"845-853"},"PeriodicalIF":2.2,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12051461/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143956165","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Chitosan-supported CuI-catalyzed cascade reaction of 2-halobenzoic acids and amidines for the synthesis of quinazolinones. 壳聚糖负载cui催化2-卤代苯甲酸与脒级联反应合成喹唑啉酮。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-04-28 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.67
Xuhong Zhao, Weishuang Li, Mengli Yang, Bojie Li, Yaoyao Zhang, Lizhen Huang, Lei Zhu
{"title":"Chitosan-supported CuI-catalyzed cascade reaction of 2-halobenzoic acids and amidines for the synthesis of quinazolinones.","authors":"Xuhong Zhao, Weishuang Li, Mengli Yang, Bojie Li, Yaoyao Zhang, Lizhen Huang, Lei Zhu","doi":"10.3762/bjoc.21.67","DOIUrl":"https://doi.org/10.3762/bjoc.21.67","url":null,"abstract":"<p><p>A chitosan-supported CuI (CS@CuI) catalyst was developed for the synthesis of quinazolinones from 2-halobenzoic acids (including iodine and bromine) and amidines. The reaction proceeds under mild reaction conditions, demonstrating a broad substrate scope (30 examples) and good catalytic efficiency (up to 99% yield).</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"839-844"},"PeriodicalIF":2.2,"publicationDate":"2025-04-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12051478/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143964542","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
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