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Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles. 可见光促进苯并咪唑中未活化烯烃的自由基环化：二氟甲基和芳基二氟甲基取代多环咪唑的合成。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-30 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.15
Yujun Pang, Jinglan Yan, Nawaf Al-Maharik, Qian Zhang, Zeguo Fang, Dong Li
{"title":"Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles.","authors":"Yujun Pang, Jinglan Yan, Nawaf Al-Maharik, Qian Zhang, Zeguo Fang, Dong Li","doi":"10.3762/bjoc.21.15","DOIUrl":"10.3762/bjoc.21.15","url":null,"abstract":"<p><p>An efficient and eco-friendly approach for synthesizing difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles was established via a visible-light-promoted radical cyclization reaction. This method employed the readily accessible and inexpensive CF<sub>2</sub>HCO<sub>2</sub>H or PhCF<sub>2</sub>COOH, along with benzimidazoles bearing unactivated alkenes and PhI(OAc)<sub>2</sub> as substrates, and proceeded without the need of any base, metal catalyst, photocatalyst or additive. In total, 24 examples were examined, and all of them successfully underwent cyclization reaction to produce the target products in good to excellent yields. Mechanistic studies revealed that the reaction proceeds via a radical pathway.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"234-241"},"PeriodicalIF":2.2,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11789676/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143121854","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
Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization. 通过铜催化的三组分组装和金促进的6-内环环化，流线型模块化合成萨弗霉素亚结构。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-28 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.14
Asahi Kanno, Ryo Tanifuji, Satoshi Yoshida, Sota Sato, Saori Maki-Yonekura, Kiyofumi Takaba, Jungmin Kang, Kensuke Tono, Koji Yonekura, Hiroki Oguri
{"title":"Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-<i>endo</i> cyclization.","authors":"Asahi Kanno, Ryo Tanifuji, Satoshi Yoshida, Sota Sato, Saori Maki-Yonekura, Kiyofumi Takaba, Jungmin Kang, Kensuke Tono, Koji Yonekura, Hiroki Oguri","doi":"10.3762/bjoc.21.14","DOIUrl":"10.3762/bjoc.21.14","url":null,"abstract":"<p><p>The integration of copper(I)-catalyzed three-component coupling with gold(I)-mediated 6-<i>endo</i> cyclization streamlines the rapid and modular assembly of the substructure of bis-tetrahydroisoquinoline (THIQ) alkaloids. The design of the key synthetic intermediate bearing a 2,3-diaminobenzofuran moiety allows both gold(I)-mediated regiocontrolled 6-<i>endo</i> hydroamination and temporary protection of nitrile and phenolic hydroxy groups. The synthetic strategy enabled the efficient synthesis of the substructure of saframycins bearing isoquinoline and THIQ units in just four steps from the modular assembly of the three components. We also found the unexpected involvement of a fluorescent intermediate in the cascade synthetic process.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"226-233"},"PeriodicalIF":2.2,"publicationDate":"2025-01-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11789684/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143121825","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
Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide. 利用甲酰胺制备氰乙酰胺基MCR支架。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-24 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.13
Marios Zingiridis, Danae Papachristodoulou, Despoina Menegaki, Konstantinos G Froudas, Constantinos G Neochoritis
{"title":"Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide.","authors":"Marios Zingiridis, Danae Papachristodoulou, Despoina Menegaki, Konstantinos G Froudas, Constantinos G Neochoritis","doi":"10.3762/bjoc.21.13","DOIUrl":"10.3762/bjoc.21.13","url":null,"abstract":"<p><p>C1 chemistry has a central role in the efficient utilization of single-carbon molecules, contributing significantly to sustainability, innovation and economic growth across various sectors. In this study, we present an efficient and rapid method for synthesizing a variety of heteroannulated pyrimidones using cyanoacetamide-based multicomponent reaction (MCR) chemistry. By utilizing specific MCR-based scaffolds as precursors and employing the abundant and inexpensive formamide as a C1 feedstock under neat conditions, we were able to efficiently access substituted thieno-, quinolino- and indolopyrimidones without the need of column chromatography. Further, a single-crystal X-ray structure was obtained, revealing certain geometrical features.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"217-225"},"PeriodicalIF":2.2,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11773184/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143057879","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
Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations. 二恶唑酮作为亲电酰胺源在铜催化和介导转化中的应用。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-22 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.12
Seungmin Lee, Minsuk Kim, Hyewon Han, Jongwoo Son
{"title":"Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations.","authors":"Seungmin Lee, Minsuk Kim, Hyewon Han, Jongwoo Son","doi":"10.3762/bjoc.21.12","DOIUrl":"10.3762/bjoc.21.12","url":null,"abstract":"<p><p>Over the past decade, dioxazolones have been widely used as <i>N</i>-acylamide sources in amidation processes of challenging substrates, typically employing precious transition metals. However, these catalytic systems often present several challenges associated with cost, toxicity, stability, and recyclability. Among the 3d transition metals, copper catalysts have been gaining increasing attention owing to their abundance, cost-effectiveness, and sustainability. Recently, these catalytic systems have been applied to the chemical transformation of dioxazolones, conferring a convenient protocol towards amidated products. This review highlights recent advancements in the synthetic transformations of dioxazolones, with particular examples of copper salts.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"200-216"},"PeriodicalIF":2.2,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11773186/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143057877","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
Quantifying the ability of the CF2H group as a hydrogen bond donor. 量化CF2H基团作为氢键给体的能力。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-20 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.11
Matthew E Paolella, Daniel S Honeycutt, Bradley M Lipka, Jacob M Goldberg, Fang Wang
{"title":"Quantifying the ability of the CF<sub>2</sub>H group as a hydrogen bond donor.","authors":"Matthew E Paolella, Daniel S Honeycutt, Bradley M Lipka, Jacob M Goldberg, Fang Wang","doi":"10.3762/bjoc.21.11","DOIUrl":"10.3762/bjoc.21.11","url":null,"abstract":"<p><p>The CF<sub>2</sub>H group can act as a hydrogen bond donor, serving as a potential surrogate for OH or SH groups but with a weaker hydrogen bond donation ability. Here, we describe a series of CF<sub>2</sub>H group-containing moieties that facilitate hydrogen bond interactions. We survey hydrogen bond donation ability using several established methods, including <sup>1</sup>H NMR-based hydrogen bond acidity determination, UV-vis spectroscopy titration with Reichardt's dye, and <sup>1</sup>H NMR titration using tri-<i>n</i>-butylphosphine oxide as a hydrogen bond acceptor. Our experiments reveal that the direct attachment of the CF<sub>2</sub>H group to cationic aromatic systems significantly enhances its hydrogen bond donation ability, a result consistent with theoretical calculations. We anticipate that this chemistry will be valuable for designing functional molecules for chemical biology and medicinal chemistry applications.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"189-199"},"PeriodicalIF":2.2,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11773185/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143057880","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
Hydrogen-bonded macrocycle-mediated dimerization for orthogonal supramolecular polymerization. 正交超分子聚合中氢键大环介导的二聚化。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-17 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.10
Wentao Yu, Zhiyao Yang, Chengkan Yu, Xiaowei Li, Lihua Yuan
{"title":"Hydrogen-bonded macrocycle-mediated dimerization for orthogonal supramolecular polymerization.","authors":"Wentao Yu, Zhiyao Yang, Chengkan Yu, Xiaowei Li, Lihua Yuan","doi":"10.3762/bjoc.21.10","DOIUrl":"10.3762/bjoc.21.10","url":null,"abstract":"<p><p>Orthogonal self-assembly represents a useful methodology to construct supramolecular polymers with AA- and AB-type monomers, as commonly used for covalently linked polymers. So far, the design of such monomers has relied heavily on three-dimensional macrocycles, and the use of two-dimensional shape-persistent macrocycles for this purpose remains rather rare. Here, we demonstrate a dimerization motif based on a hydrogen-bonded macrocycle that can be effectively applied to form orthogonal supramolecular polymers. The macrocycle-mediated connectivity was confirmed by single-crystal X-ray diffraction, which revealed a unique 2:2 binding motif between host and guest, bridged by two cationic pyridinium end groups through π-stacking interactions and other cooperative intermolecular forces. Zinc ion-induced coordination with the macrocycle and a terpyridinium derivative enabled orthogonal polymerization, as revealed by <sup>1</sup>H NMR, DLS, and TEM techniques. In addition, viscosity measurements showed a transition from oligomers to polymers at the critical polymerization concentration of 17 μM. These polymers were highly concentration-dependent. Establishing this new dimerization motif with shape-persistent H-bonded macrocycles widens the scope of noncovalent building blocks for supramolecular polymers and augurs well for the future development of functional materials.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"179-188"},"PeriodicalIF":2.2,"publicationDate":"2025-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11744735/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142999271","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 electrochemical copper catalysis for modern organic synthesis. 电化学铜催化现代有机合成研究进展。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-16 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.9
Yemin Kim, Won Jun Jang
{"title":"Recent advances in electrochemical copper catalysis for modern organic synthesis.","authors":"Yemin Kim, Won Jun Jang","doi":"10.3762/bjoc.21.9","DOIUrl":"10.3762/bjoc.21.9","url":null,"abstract":"<p><p>In recent decades, organic electrosynthesis has emerged as a practical, sustainable, and efficient approach that facilitates valuable transformations in synthetic chemistry. Combining electrochemistry with transition-metal catalysis is a promising and rapidly growing methodology for effectively forming challenging C-C and C-heteroatom bonds in complex molecules in a sustainable manner. In this review, we summarize the recent advances in the combination of electrochemistry and copper catalysis for various organic transformations.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"155-178"},"PeriodicalIF":2.2,"publicationDate":"2025-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11744695/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142999275","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
Nickel-catalyzed cross-coupling of 2-fluorobenzofurans with arylboronic acids via aromatic C-F bond activation. 镍催化芳香C-F键活化2-氟苯并呋喃与芳基硼酸的交叉偶联。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-15 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.8
Takeshi Fujita, Haruna Yabuki, Ryutaro Morioka, Kohei Fuchibe, Junji Ichikawa
{"title":"Nickel-catalyzed cross-coupling of 2-fluorobenzofurans with arylboronic acids via aromatic C-F bond activation.","authors":"Takeshi Fujita, Haruna Yabuki, Ryutaro Morioka, Kohei Fuchibe, Junji Ichikawa","doi":"10.3762/bjoc.21.8","DOIUrl":"10.3762/bjoc.21.8","url":null,"abstract":"<p><p>2-Fluorobenzofurans underwent efficient nickel-catalyzed coupling with arylboronic acids through the activation of aromatic C-F bonds. This method allowed us to successfully synthesize a range of 2-arylbenzofurans with various substituents. The reaction, which proceeded under mild conditions, involved β-fluorine elimination from nickelacyclopropanes formed by the interaction of 2-fluorobenzofurans with zero-valent nickel species. This protocol facilitates orthogonal coupling reactions of aromatic C-F and C-Br bonds with arylboronic acids.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"146-154"},"PeriodicalIF":2.2,"publicationDate":"2025-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11744694/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142999273","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(OTf)2-catalyzed multicomponent reactions. Cu(OTf)2催化的多组分反应。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-14 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.7
Sara Colombo, Camilla Loro, Egle M Beccalli, Gianluigi Broggini, Marta Papis
{"title":"Cu(OTf)<sub>2</sub>-catalyzed multicomponent reactions.","authors":"Sara Colombo, Camilla Loro, Egle M Beccalli, Gianluigi Broggini, Marta Papis","doi":"10.3762/bjoc.21.7","DOIUrl":"10.3762/bjoc.21.7","url":null,"abstract":"<p><p>This review reports the achievements in copper(II) triflate-catalyzed processes concerning the multicomponent reactions, applied to the synthesis of acyclic and cyclic compounds. In particular, for the heteropolycyclic systems mechanistic insights were outlined as well as cycloaddition and aza-Diels-Alder reactions were included. These strategies have gained attention due to their highly atom- and step-economy, one-step multi-bond forming, mild reaction conditions, low cost and easy handling.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"122-145"},"PeriodicalIF":2.2,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11744696/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142999232","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 organocatalytic atroposelective reactions. 有机催化反选择性反应的最新进展。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-09 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.6
Henrich Szabados, Radovan Šebesta
{"title":"Recent advances in organocatalytic atroposelective reactions.","authors":"Henrich Szabados, Radovan Šebesta","doi":"10.3762/bjoc.21.6","DOIUrl":"10.3762/bjoc.21.6","url":null,"abstract":"<p><p>Axial chirality is present in a variety of naturally occurring compounds, and is becoming increasingly relevant also in medicine. Many axially chiral compounds are important as catalysts in asymmetric catalysis or have chiroptical properties. This review overviews recent progress in the synthesis of axially chiral compounds via asymmetric organocatalysis. Atroposelective organocatalytic reactions are discussed according to the dominant catalyst activation mode. For covalent organocatalysis, the typical enamine and iminium modes are presented, followed by <i>N</i>-heterocyclic carbene-catalyzed reactions. The bulk of the review is devoted to non-covalent activation, where chiral Brønsted acids feature as the most prolific catalytic structure. The last part of the article discusses hydrogen-bond-donating catalysts and other catalyst motifs such as phase-transfer catalysts.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"55-121"},"PeriodicalIF":2.2,"publicationDate":"2025-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11729692/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142982577","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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