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.
{"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}
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.
{"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}
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.
在酸催化条件下，将一个等效的吩嗪基三吡喃与一个等效的适当的 2.5-双(羟甲基-对甲苯基)杂环缩合，合成了一系列含有一个吩嗪、两个吡咯和一个杂环（如呋喃、噻吩、硒吩和碲吩）的吩嗪内嵌杂卟啉，并将它们的结构、光谱和电化学性质与之前报道的吩噻嗪内嵌杂卟啉进行了比较、在酸催化条件下，将一个等量的吩嗪基三吡喃与一个等量的适当的 2、5-双（羟甲基-对甲苯基）杂环缩合合成了吩嗪基三吡喃和碲吩，并将它们的结构、光谱和电化学性质与之前报道的吩噻嗪嵌入杂卟啉进行了比较。嵌入吩噁嗪的硒卟啉的 X 射线晶体结构显示，与吩噁嗪分子相对的硒吩环指向大环核心的外侧，吩噁嗪单元与四个中碳原子定义的平均平面偏离 39.47° 角。用吩噁嗪单元取代吩噻嗪嵌入杂卟啉中的吩噻嗪单元会显著改变大环的电子特性，这反映在它们的光谱和电化学特性上。与相应的吩噻嗪内嵌杂卟啉相比，吩嗪内嵌杂卟啉的吸收光谱显示了浴色偏移的吸收带和次浴色偏移的荧光带，量子产率较高，更容易氧化和更难还原。DFT 和 TD-DFT 研究证实了实验观察结果。
{"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}
Rabeb Ben Romdhane, Linhao Liu, Ridha Ben Salem, Henri Doucet
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.
{"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}
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.
{"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}
Jan Radolko, Ha N Do, Peter Ehlers, Alexander Villinger, Peter Langer
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.
{"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}
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.
{"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}
Tianbo Shang, Chao Ma, Mengyu Xie, Tao Cai, Yuzhen Gao
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.
{"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}
Recent advances in the continuous synthesis of ionic liquids and SILP-assisted continuous processes are reviewed in this manuscript. These catalyst frameworks still provide an attractive strategy in many organic transformations and provide a suitable tool for designing new synthetic approaches. This review focuses on recent developments in the research area from 2016 up until today.
{"title":"Flowing Forward: Continuous Synthesis of and with Ionic Liquids","authors":"Kristof Stagel, Katharina Bica-Schröder","doi":"10.1002/ejoc.202400917","DOIUrl":"https://doi.org/10.1002/ejoc.202400917","url":null,"abstract":"Recent advances in the continuous synthesis of ionic liquids and SILP-assisted continuous processes are reviewed in this manuscript. These catalyst frameworks still provide an attractive strategy in many organic transformations and provide a suitable tool for designing new synthetic approaches. This review focuses on recent developments in the research area from 2016 up until today.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","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":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The synthesis of axially chiral carbonyl compounds has attracted considerable interest in organic synthesis due to their prevalence in natural products and pharmaceuticals, as well as their utility in material science and catalysis. Transition‐metal‐catalyzed approaches have become powerful tools for their construction, offering high efficiency, selectivity, and versatility among the various methods developed. This concept aims to provide a comprehensive overview of recent advances in the transition‐metal‐catalyzed asymmetric synthesis of axially chiral carbonyl compounds, integrating scattered work with different catalytic systems. This feature concept is divided into four types of reactions based on the strategies employed: cross‐coupling reactions, cycloaddition reactions, desymmetrization reactions, and other C‒H activation reactions.
{"title":"Transition‐Metal‐Catalyzed Construction of Axially Chiral Carbonyl Compounds","authors":"Yu Yan, Min Pan, Jialin Ming, Jun-Ping Yue, Xiao-Wang Chen, Yong-Yuan Gui, Da-Gang Yu","doi":"10.1002/ejoc.202400995","DOIUrl":"https://doi.org/10.1002/ejoc.202400995","url":null,"abstract":"The synthesis of axially chiral carbonyl compounds has attracted considerable interest in organic synthesis due to their prevalence in natural products and pharmaceuticals, as well as their utility in material science and catalysis. Transition‐metal‐catalyzed approaches have become powerful tools for their construction, offering high efficiency, selectivity, and versatility among the various methods developed. This concept aims to provide a comprehensive overview of recent advances in the transition‐metal‐catalyzed asymmetric synthesis of axially chiral carbonyl compounds, integrating scattered work with different catalytic systems. This feature concept is divided into four types of reactions based on the strategies employed: cross‐coupling reactions, cycloaddition reactions, desymmetrization reactions, and other C‒H activation reactions.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"26 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142561908","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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