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First Total Synthesis of Deinococcucin A, a Key Glycolipid Found in Cell Membranes of Extremophilic Bacteria. 嗜极细菌细胞膜中的一种关键糖脂--Deinococcucin A 的首次全合成。
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-11-06 DOI: 10.1002/ejoc.202400879
Jonathan Martins, Abed Bil, José Kovensky, Sylvestre Toumieux, Sylvain Laclef
{"title":"First Total Synthesis of Deinococcucin A, a Key Glycolipid Found in Cell Membranes of Extremophilic Bacteria.","authors":"Jonathan Martins, Abed Bil, José Kovensky, Sylvestre Toumieux, Sylvain Laclef","doi":"10.1002/ejoc.202400879","DOIUrl":"https://doi.org/10.1002/ejoc.202400879","url":null,"abstract":"Deinococcucin A is a secondary metabolite isolated from a gut bacteria of carpenter ant, member of extremophilic Deinoccocus family. The structure is a glycolipid containing N-acetyl glucosamine, linked in α anomeric position to a chiral 2,3-dihydroxypropanamide moiety. We succeeded a new strategy starting directly from N-acetylglucosamine and transforming in an efficient manner an allyl group to the corresponding chiral α-hydroxyamide. Three key steps were used: the oxidation of primary amine to nitrile using TCCA, as well as its hydrolysis to the corresponding amide using palladium (II) catalyzed conditions. The synthesis was completed in only 10 steps with an overall yield of 3%.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"68 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142588979","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
Photooxidation of Polystyrene into High-Value Chemicals 将聚苯乙烯光氧化成高价值化学品
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-11-05 DOI: 10.1002/ejoc.202401109
Shusheng Jiang, Yunhan Chen, Yahao Huang, Peng Hu
{"title":"Photooxidation of Polystyrene into High-Value Chemicals","authors":"Shusheng Jiang, Yunhan Chen, Yahao Huang, Peng Hu","doi":"10.1002/ejoc.202401109","DOIUrl":"https://doi.org/10.1002/ejoc.202401109","url":null,"abstract":"Plastics play a crucial role in the survival and advancement of human civilization. However, the increasing challenge of plastic pollution presents significant obstacles. Disposal methods such as incineration and landfilling result in substantial resource wastage and pose potential environmental hazards. The slow progress in recycling and reusing waste plastics hinders their industrial application and effective response to environmental crises. Photocatalysis offers promising solutions for the future of plastic recycling, particularly with the recent increase in photocatalytic degradation methods for polystyrene (PS). This review provides a comprehensive overview of the latest advancements in the photooxidation of PS into high-value chemicals.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"17 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142580272","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
Palladium-Catalyzed Domino Synthesis of Sulfone-Containing 1,3-Enynes from Simple Alkynes and Sulfonyl Iodides 钯催化的由简单炔烃和磺酰基碘化物合成含砜 1,3-Enynes 的多米诺反应
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-11-05 DOI: 10.1002/ejoc.202401028
Jing Wang, Jianwei Wang, Jun Ying
{"title":"Palladium-Catalyzed Domino Synthesis of Sulfone-Containing 1,3-Enynes from Simple Alkynes and Sulfonyl Iodides","authors":"Jing Wang, Jianwei Wang, Jun Ying","doi":"10.1002/ejoc.202401028","DOIUrl":"https://doi.org/10.1002/ejoc.202401028","url":null,"abstract":"A palladium-catalyzed domino radical sulfonylation and alkynylation of simple alkynes has been developed for the rapid construction of privileged scaffolds containing sulfone and 1,3-enyne motifs. The reaction of sulfonyl iodide with simple alkynes proceeded smoothly under mild conditions to afford a variety of sulfone-containing 1,3-enynes in good yields and with excellent selectivities.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"150 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142588981","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, Structure, Spectral and Redox Properties of Phenoxazine Embedded Heteroporphyrins 嵌入吩嗪的杂卟啉的合成、结构、光谱和氧化还原特性
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-11-05 DOI: 10.1002/ejoc.202401068
Neha Tripathi, Mangalampalli Ravikanth
{"title":"Synthesis, Structure, Spectral and Redox Properties of Phenoxazine Embedded Heteroporphyrins","authors":"Neha Tripathi, Mangalampalli Ravikanth","doi":"10.1002/ejoc.202401068","DOIUrl":"https://doi.org/10.1002/ejoc.202401068","url":null,"abstract":"A series of phenoxazine embedded heteroporphyrins containing one phenoxazine, two pyrroles and one heterocycle, such as furan, thiophene, selenophene and telluorophene, connected through four meso carbon atoms were synthesized by condensing one equivalent of phenoxazine-based tripyrrane with one equivalent of the appropriate 2,5-bis(hydroxymethyl-p-tolyl) heterocycle under acid-catalyzed conditions, and their structure, spectral and electrochemical properties were compared with those of previously reported phenothiazine embedded heteroporphyrins. The X-ray crystal structure of the phenoxazine embedded selenoporphyrin revealed that the selenophene ring, which is opposite phenoxazine moiety, points outward from the macrocyclic core, and the phenoxazine unit deviated by an angle of 39.47° from the mean plane defined by the four meso carbons atoms. The replacement of the phenothiazine unit in phenothiazine embedded heteroporphyrins with a phenoxazine unit led to significant alteration of the electronic properties of the macrocycles, as reflected in their spectral and electrochemical properties. The absorption spectra of phenoxazine embedded heteroporphyrins showed bathochromically shifted absorption bands, hypsochromically shifted fluorescence bands with decent quantum yields, more facile oxidation and more difficult reduction as compared to the corresponding phenothiazine embedded heteroporphyrins. DFT and TD-DFT studies were in support of the experimental observations.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142588982","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
Palladium-Catalyzed C4,C5-Diarylation of Isoxazole-3-carboxylate by Double C–H Bond Functionalization 钯催化双 C-H 键官能化异恶唑-3-羧酸酯的 C4、C5-二芳基化反应
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-11-04 DOI: 10.1002/ejoc.202401036
Rabeb Ben Romdhane, Linhao Liu, Ridha Ben Salem, Henri Doucet
{"title":"Palladium-Catalyzed C4,C5-Diarylation of Isoxazole-3-carboxylate by Double C–H Bond Functionalization","authors":"Rabeb Ben Romdhane, Linhao Liu, Ridha Ben Salem, Henri Doucet","doi":"10.1002/ejoc.202401036","DOIUrl":"https://doi.org/10.1002/ejoc.202401036","url":null,"abstract":"The Pd-catalyzed C4-arylation of 3,5-disubstituted isoxazoles via C-H bond functionalization has been largely described. By contrast, the reactivity of isoxazoles in C-H bond functionalization with both unsubstituted C4 and C5 positions remains largely unexplored. Herein, we report on the reactivity in Pd-catalyzed double C-H bond arylation of an isoxazole with unsubstituted C4 and C5 positions. Conditions for the palladium-catalyzed direct C4,C5-diarylation of ethyl isoxazole-3-carboxylate using aryl bromides as the aryl source are reported. This procedure tolerates several useful substituents on the aryl bromide such as nitrile, acetyl, formyl, benzoyl, alkoxycarbonyl, chloro, fluoro, trifluoromethyl, trifluoromethoxy, cyanomethyl,tertbutyl and methoxy at para- and meta-positions. Conversely, with ortho-substituted aryl bromides, mixtures of mono- and di-arylated isoxazoles were generally obtained. This methodology provides a simple one pot access to a wide variety of C4,C5-diarylated isoxazoles from commercially available substrates allowing to modify easily their biological properties.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"142 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142574416","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
Chiral Secondary Phosphine Oxide Ligands in Asymmetric Ni–Al Bimetallic Catalysis 不对称 Ni-Al 双金属催化中的手性仲膦氧化物配体
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-11-02 DOI: 10.1002/ejoc.202401000
Mengying Xu, Weiwei Xu, Mengchun Ye
{"title":"Chiral Secondary Phosphine Oxide Ligands in Asymmetric Ni–Al Bimetallic Catalysis","authors":"Mengying Xu, Weiwei Xu, Mengchun Ye","doi":"10.1002/ejoc.202401000","DOIUrl":"https://doi.org/10.1002/ejoc.202401000","url":null,"abstract":"Ligands play a key role in asymmetric transition-metal catalysis. Among reported chiral ligands, readily available and air-stable secondary phosphine oxide ligands are unique and have aroused wide interest in Ni–Al bimetallic catalysis, since they can act as bifunctional ligands to ligate two metals for stronger bimetallic synergism, greatly enhancing reactivity and selectivity. Hence, in this mini review we will focus on secondary phosphine oxides and their applications in asymmetric Ni-Al bimetallic catalysis.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"33 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142563220","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 and Properties of 6-Oxazaaceanthrylenes 6-Oxazaaceanthrylenes 的合成与特性
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-11-01 DOI: 10.1002/ejoc.202401045
Jan Radolko, Ha N Do, Peter Ehlers, Alexander Villinger, Peter Langer
{"title":"Synthesis and Properties of 6-Oxazaaceanthrylenes","authors":"Jan Radolko, Ha N Do, Peter Ehlers, Alexander Villinger, Peter Langer","doi":"10.1002/ejoc.202401045","DOIUrl":"https://doi.org/10.1002/ejoc.202401045","url":null,"abstract":"6‑Oxazaaceanthrylenes have been synthesized for the first time via a selective SNAr reaction or Ullmann-coupling of phenols, followed by a C-H activation reaction. The reaction has been carefully optimized and permits the selective synthesis of N,O-doped aceanthrylenes in moderate to excellent yields and tolerate various functional groups. The aromatic behavior of the hitherto unknown heterocyclic scaffold has been further analyzed by NICS and NICS2BC calculations.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"6 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142562174","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
Convergent Synthesis of Antitumor Aplysiatoxin Derivatives Based on a Combination of Ring-closing and Cross Metathesis 基于闭环和交叉复分解的抗肿瘤阿立哌唑毒素衍生物的聚合合成
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-11-01 DOI: 10.1002/ejoc.202401074
Mako Aoki, Hiroto Takarada, Jumpei Maki, Takumi Kobayashi, Chihiro Tsukano, Kazuhiro Irie
{"title":"Convergent Synthesis of Antitumor Aplysiatoxin Derivatives Based on a Combination of Ring-closing and Cross Metathesis","authors":"Mako Aoki, Hiroto Takarada, Jumpei Maki, Takumi Kobayashi, Chihiro Tsukano, Kazuhiro Irie","doi":"10.1002/ejoc.202401074","DOIUrl":"https://doi.org/10.1002/ejoc.202401074","url":null,"abstract":"We investigated a convergent synthesis of aplysiatoxin analogs based on a combination of ring-closing and cross metathesis. The route provided four analogs (3a–d) with different side chains to determine the CH/π interaction with protein kinase C (PKC)-C1 domains. Biochemical evaluation revealed that a naphthol moiety did not improve binding to PKC-C1 domains, suggesting that the hydrogen bonding of the hydroxy group with the PKC-C1 domains may be more important than the CH/π interaction.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"33 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142562204","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
Developments in the Construction of Benzo[b]thiophenes from 2-Alkynylthioanisoles by Electrophilic and Radical Cyclization Reactions 通过亲电和自由基环化反应从 2-炔基硫代苯甲醚构建苯并[b]噻吩的研究进展
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-11-01 DOI: 10.1002/ejoc.202401059
Tianbo Shang, Chao Ma, Mengyu Xie, Tao Cai, Yuzhen Gao
{"title":"Developments in the Construction of Benzo[b]thiophenes from 2-Alkynylthioanisoles by Electrophilic and Radical Cyclization Reactions","authors":"Tianbo Shang, Chao Ma, Mengyu Xie, Tao Cai, Yuzhen Gao","doi":"10.1002/ejoc.202401059","DOIUrl":"https://doi.org/10.1002/ejoc.202401059","url":null,"abstract":"Benzo[b]thiophene moieties are important skeletons which have been widely found in many natural products, pharmaceuticals, as well as functionalized materials. 2-Alkynylthioanisoles, a class of bifunctional compounds bearing methylthio and alkynyl groups, are easily accessible from Pd-catalyzed Sonogashira coupling between 2-halothioanisoles and terminal alkynes, which have been widely employed as synthons in the construction of benzo[b]thiophenes through an electrophilic or a radical pathway. This review summarizes the related developments with a particular focus on the reaction mechanism. We hope it will help in future research in this area and believe that with the discovery of new catalytic systems, the industrial synthesis of benzo[b]thiophenes from 2-alkynylthioanisoles will be achieved soon.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"117 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142562173","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
Flowing Forward: Continuous Synthesis of and with Ionic Liquids 向前流动：离子液体的连续合成和使用离子液体的连续合成
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-11-01 DOI: 10.1002/ejoc.202400917
Kristof Stagel, Prof. Katharina Bica-Schröder
{"title":"Flowing Forward: Continuous Synthesis of and with Ionic Liquids","authors":"Kristof Stagel,&nbsp;Prof. Katharina Bica-Schröder","doi":"10.1002/ejoc.202400917","DOIUrl":"10.1002/ejoc.202400917","url":null,"abstract":"<p>Herein, the developments in the field of continuous ionic liquid synthesis and continuous ionic liquid utilization from the last seven years are reviewed. Starting by discussing recent strategies for the preparation of ionic liquids themselves in different flow reactors, the review will further focus on various continuous strategies employing ionic liquids. The application of ionic liquids in continuous processes, particularly as supported catalytic layers, has drawn significant scientific interest in the last decades. These catalyst frameworks provide a versatile tool in many organic transformations, and their application became an attractive strategy in continuous catalytic approaches.</p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"27 47","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202400917","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142563322","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
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