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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":"https://doi.org/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":"https://doi.org/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":"https://doi.org/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":"https://doi.org/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
Hot shape transformation: the role of PSar dehydration in stomatocyte morphogenesis. 热形态转化：PSar脱水在气孔细胞形态发生中的作用。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-08 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.5
Remi Peters, Levy A Charleston, Karinan van Eck, Teun van Berlo, Daniela A Wilson
{"title":"Hot shape transformation: the role of PSar dehydration in stomatocyte morphogenesis.","authors":"Remi Peters, Levy A Charleston, Karinan van Eck, Teun van Berlo, Daniela A Wilson","doi":"10.3762/bjoc.21.5","DOIUrl":"10.3762/bjoc.21.5","url":null,"abstract":"<p><p>Polysarcosine emerges as a promising alternative to polyethylene glycol (PEG) in biomedical applications, boasting advantages in biocompatibility and degradability. While the self-assembly behavior of block copolymers containing polysarcosine-containing polymers has been reported, their potential for shape transformation remains largely untapped, limiting their versatility across various applications. In this study, we present a comprehensive methodology for synthesizing, self-assembling, and transforming polysarcosine-poly(benzyl glutamate) block copolymers, resulting in the formation of bowl-shaped vesicles, disks, and stomatocytes. Under ambient conditions, the shape transformation is restricted to bowl-shaped vesicles due to the membrane's flexibility and permeability. However, dehydration of the polysarcosine broadens the possibilities for shape transformation. These novel structures exhibit asymmetry and possess the capability to encapsulate smaller structures, thereby broadening their potential applications in drug delivery and nanotechnology. Our findings shed light on the unique capabilities of polysarcosine-based polymers, paving the way for further exploration and harnessing of their distinctive properties in biomedical research.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"47-54"},"PeriodicalIF":2.2,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11729680/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142982576","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
Facile one-pot reduction of β-nitrostyrenes to phenethylamines using sodium borohydride and copper(II) chloride. 用硼氢化钠和氯化铜一锅简易还原β-硝基苯乙烯为苯乙胺。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-07 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.4
Laura D'Andrea, Simon Jademyr
{"title":"Facile one-pot reduction of β-nitrostyrenes to phenethylamines using sodium borohydride and copper(II) chloride.","authors":"Laura D'Andrea, Simon Jademyr","doi":"10.3762/bjoc.21.4","DOIUrl":"10.3762/bjoc.21.4","url":null,"abstract":"<p><p>Phenethylamines and phenylisopropylamines of scientific relevance can be prepared with a NaBH<sub>4</sub>/CuCl<sub>2</sub> system in 10 to 30 minutes via reduction of substituted β-nitrostyrenes. This one-pot procedure allows the quick isolation of substituted β-nitrostyrene scaffolds with 62-83% yield under mild conditions, without the need for special precautions, inert atmosphere, and time-consuming purification techniques.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"39-46"},"PeriodicalIF":2.2,"publicationDate":"2025-01-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11729678/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142982574","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
Emerging trends in the optimization of organic synthesis through high-throughput tools and machine learning. 通过高通量工具和机器学习优化有机合成的新趋势。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-06 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.3
Pablo Quijano Velasco, Kedar Hippalgaonkar, Balamurugan Ramalingam
{"title":"Emerging trends in the optimization of organic synthesis through high-throughput tools and machine learning.","authors":"Pablo Quijano Velasco, Kedar Hippalgaonkar, Balamurugan Ramalingam","doi":"10.3762/bjoc.21.3","DOIUrl":"10.3762/bjoc.21.3","url":null,"abstract":"<p><p>The discovery of the optimal conditions for chemical reactions is a labor-intensive, time-consuming task that requires exploring a high-dimensional parametric space. Historically, the optimization of chemical reactions has been performed by manual experimentation guided by human intuition and through the design of experiments where reaction variables are modified one at a time to find the optimal conditions for a specific reaction outcome. Recently, a paradigm change in chemical reaction optimization has been enabled by advances in lab automation and the introduction of machine learning algorithms. Therein, multiple reaction variables can be synchronously optimized to obtain the optimal reaction conditions, requiring a shorter experimentation time and minimal human intervention. Herein, we review the currently used state-of-the-art high-throughput automated chemical reaction platforms and machine learning algorithms that drive the optimization of chemical reactions, highlighting the limitations and future opportunities of this new field of research.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"10-38"},"PeriodicalIF":2.2,"publicationDate":"2025-01-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11730176/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142982573","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
Chemical glycobiology. 化学糖生物学。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-03 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.2
Elisa Fadda, Rachel Hevey, Benjamin Schumann, Ulrika Westerlind
{"title":"Chemical glycobiology.","authors":"Elisa Fadda, Rachel Hevey, Benjamin Schumann, Ulrika Westerlind","doi":"10.3762/bjoc.21.2","DOIUrl":"https://doi.org/10.3762/bjoc.21.2","url":null,"abstract":"","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"8-9"},"PeriodicalIF":2.2,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11702292/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142943556","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
Synthesis, structure and π-expansion of tris(4,5-dehydro-2,3:6,7-dibenzotropone). 三（4,5-脱氢-2,3:6,7-二苯并苯托酮）的合成、结构及π扩张。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-02 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.1
Yongming Xiong, Xue Lin Ma, Shilong Su, Qian Miao
{"title":"Synthesis, structure and π-expansion of tris(4,5-dehydro-2,3:6,7-dibenzotropone).","authors":"Yongming Xiong, Xue Lin Ma, Shilong Su, Qian Miao","doi":"10.3762/bjoc.21.1","DOIUrl":"https://doi.org/10.3762/bjoc.21.1","url":null,"abstract":"<p><p>The polycyclic skeleton of tris(4,5-dehydro-2,3:6,7-dibenzotropone) is a key structural fragment in carbon schwarzites, a theoretical form of negatively curved carbon allotrope. This report presents a new synthesis of this compound using a Ni-mediated Yamamoto coupling reaction and structural analysis of it with X-ray crystallography. Interestingly, it is observed that tris(4,5-dehydro-2,3:6,7-dibenzotropone) crystallized from its solution in hexane resulting in colorless and yellow crystal polymorphs, where it adopts conformations of approximate <i>C</i> <i><sub>s</sub></i> and <i>C</i> <sub>2</sub> symmetry, respectively. Furthermore, expanding its π-skeleton through the Barton-Kellogg and Scholl reactions led to the successful synthesis of a curved polycyclic arene containing three heptagons and two pentagons.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1-7"},"PeriodicalIF":2.2,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11702293/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142943557","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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