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Directing‐Group‐Assisted Markovnikov Hydroximation of Styrenes Enabled by Photoredox/Cobalt Dual‐Catalysis 光氧化还原/钴双催化实现苯乙烯定向基团辅助Markovnikov氢化反应
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202401156
Qian Xiao , Maojian Lu , Yonghong Xiao , Jian‐Ji Zhong
{"title":"Directing‐Group‐Assisted Markovnikov Hydroximation of Styrenes Enabled by Photoredox/Cobalt Dual‐Catalysis","authors":"Qian Xiao ,&nbsp;Maojian Lu ,&nbsp;Yonghong Xiao ,&nbsp;Jian‐Ji Zhong","doi":"10.1002/ejoc.202401156","DOIUrl":"10.1002/ejoc.202401156","url":null,"abstract":"<div><div>By the combination of acridinium salt as a photocatalyst and cobaloxime complex as a co‐catalyst, a simple and mild approach has been developed for the directing‐group‐assisted Markovnikov‐selective hydroximation of styrenes under visible‐light irradiation. Herein, the directing‐group on styrenes plays an important role for this transformation. Although the substrate scope seems to be limited, such an approach features excellent regioselectivity and high atom economy. In contrast with previous methodologies, this photoredox/cobalt dual‐catalytic system is operationally simple, and avoids the use of any other sacrificial reagents.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202401156"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142975555","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
Photoinduced Gem‐Difluoroallylic Ketones Formation via Selective Carbonyl – C(sp3) Bond Cleavage of β‐Ketone Alcohols 通过选择性羰基- C（sp3）键裂解β-酮醇形成光诱导宝石-二氟烯丙基酮
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202401149
Qianwei Zhu , Zhong Zhang , Hongquan Yu , Chenglong Yuan , Lu Wang , Zhixiang Wang , Tiantao Liu , Hongxia Xu , Youqing Yang
{"title":"Photoinduced Gem‐Difluoroallylic Ketones Formation via Selective Carbonyl – C(sp3) Bond Cleavage of β‐Ketone Alcohols","authors":"Qianwei Zhu ,&nbsp;Zhong Zhang ,&nbsp;Hongquan Yu ,&nbsp;Chenglong Yuan ,&nbsp;Lu Wang ,&nbsp;Zhixiang Wang ,&nbsp;Tiantao Liu ,&nbsp;Hongxia Xu ,&nbsp;Youqing Yang","doi":"10.1002/ejoc.202401149","DOIUrl":"10.1002/ejoc.202401149","url":null,"abstract":"<div><div>A photoinduced reaction for the formation of <em>gem</em>‐difluoroallylic ketones via selective <em>β</em>‐scission of <em>β</em>‐ketone alcohols with <em>α</em>‐trifluoromethyl alkenes is described. This process demonstrates a broad substrate scope for both <em>β</em>‐ketone alcohols and <em>α</em>‐trifluoromethyl alkenes. The reaction is proposed to proceed via an intramolecular PCET mechanism. The core of the strategy involves the oxidative cleavage of the carbonyl – C(sp<sup>3</sup>) bond in <em>β</em>‐ketone alcohols, facilitated by a base, to release acyl radicals, followed by the rapid addition of <em>α</em>‐trifluoromethyl alkenes. Additionally, various downstream transformations were carried out with these compounds in a one‐step operation. This protocol is also applicable to corresponding alkynylation and Minisci reactions.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202401149"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142760036","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
Divergent Synthesis of 4‐Aminotriazoles Through Click Cycloaddition and Generation of Iodonium(III) Triazoles 通过点击环加成合成4 -氨基三唑和生成碘（III）三唑
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202401273
Takumi Hayashi , Elghareeb E. Elboray , Hina Sudo , Naoko Takenaga , Hiroyuki Satake , Toshifumi Dohi
{"title":"Divergent Synthesis of 4‐Aminotriazoles Through Click Cycloaddition and Generation of Iodonium(III) Triazoles","authors":"Takumi Hayashi ,&nbsp;Elghareeb E. Elboray ,&nbsp;Hina Sudo ,&nbsp;Naoko Takenaga ,&nbsp;Hiroyuki Satake ,&nbsp;Toshifumi Dohi","doi":"10.1002/ejoc.202401273","DOIUrl":"10.1002/ejoc.202401273","url":null,"abstract":"<div><div>The divergent synthesis of 4‐amino‐1,2,3‐triazoles was accomplished through the Cu‐catalyzed cycloaddition of organic azides with alkynyliodonium(III) salts, followed by Cu‐catalyzed triazole‐amine coupling involving treatment with amines and amides. The in situ formation of 1,2,3‐triazole iodonium salts is crucial to this approach, and the utilization of a Cu‐catalyst facilitates cycloaddition and C−N bond formation. The synthesis of 1,2,3‐triazolyliodonium(III) salts proposed in this study offers advantages, including mild reaction conditions, a broad substrate scope, and operational simplicity, while also providing efficient access to a complex and diverse range of 4‐amino‐1,2,3‐triazole derivatives.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202401273"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832399","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
Chemoselective Synthesis of Tetrahydropyrimidines and Dihydropyrrolidones through Three-Component Reaction of Amines, 1,3,5-Triazinanes, and Alkyne Esters
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-07 DOI: 10.1002/ejoc.202401400
Wen-Kang Wang, Jian Zheng, Sheng-Yin Zhao
{"title":"Chemoselective Synthesis of Tetrahydropyrimidines and Dihydropyrrolidones through Three-Component Reaction of Amines, 1,3,5-Triazinanes, and Alkyne Esters","authors":"Wen-Kang Wang, Jian Zheng, Sheng-Yin Zhao","doi":"10.1002/ejoc.202401400","DOIUrl":"https://doi.org/10.1002/ejoc.202401400","url":null,"abstract":"A three-component reaction of amines, 1,3,5-triazinanes, and alkyne esters for the construction of tetrahydropyrimidines and dihydropyrrolidones derivatives was reported. Shifting the substituent group of 1,3,5-triazinanes led to the chemoselective synthesis. As three-atom synthons, aryl substituted 1,3,5-triazinanes were applied to the regioselective synthesis of tetrahydropyrimidines. Alkyl substituted 1,3,5-triazinanes working as two-atom synthons promoted intramolecular cyclization to generate dihydropyrrolidones analogues. The practicality of the developed methods was demonstrated by easy operation, catalyst-free conditions, and good functional groups tolerance.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"17 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143258795","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
Strategies for modification of tryptophan residues: recent advances and future perspectives in photo-/ electrochemical-induction, and metal catalysis
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-07 DOI: 10.1002/ejoc.202401214
Chaochao Zhang, Jun Huang, Shun Li, Fujin Huo, Yue Weng
{"title":"Strategies for modification of tryptophan residues: recent advances and future perspectives in photo-/ electrochemical-induction, and metal catalysis","authors":"Chaochao Zhang, Jun Huang, Shun Li, Fujin Huo, Yue Weng","doi":"10.1002/ejoc.202401214","DOIUrl":"https://doi.org/10.1002/ejoc.202401214","url":null,"abstract":"Recent advancements in tryptophan (Trp) modification have greatly expanded its applications across drug discovery, materials science, and environmental monitoring. Trp, an essential amino acid with a unique indole ring, serves as an ideal target for chemical modification due to its redox-active nature. Photo- and electrochemical methods, which utilize light and electric energy, respectively, offer precise, efficient, and environmentally friendly approaches for Trp modification. Photochemical-induced transformations improve Trp's optical properties, such as fluorescence, enhancing its utility in bioimaging and sensor applications, while also introducing bioactive functional groups. Electrochemical modifications enable controlled oxidation and reduction, facilitating the selective addition of functional groups like hydroxyl or amino groups, essential for synthesizing Trp derivatives aimed at protein modulation. Additionally, metal-catalyzed reactions using transition metals such as palladium or copper enable site-selective modifications through C-H activation and cross-coupling, creating Trp derivatives with enhanced properties for optoelectronic and biomedical applications. These advancements highlight the potential of Trp-based bioconjugation strategies across diverse scientific disciplines.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143258797","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 of Vinyl Boronates from Aldehydes and Ketones by Peterson Olefination: Investigation of the Peterson/Boron‐Wittig Chemoselectivity
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1002/ejoc.202500033
Julien Janssens, Guillaume Berionni, Raphael Robiette
{"title":"Synthesis of Vinyl Boronates from Aldehydes and Ketones by Peterson Olefination: Investigation of the Peterson/Boron‐Wittig Chemoselectivity","authors":"Julien Janssens, Guillaume Berionni, Raphael Robiette","doi":"10.1002/ejoc.202500033","DOIUrl":"https://doi.org/10.1002/ejoc.202500033","url":null,"abstract":"We report our results on the development of the Peterson olefination using gem‐borylsilylmethane derivatives to synthesize di‐ and tri‐substituted vinyl boronates. We show that the electronic properties of the carbonyl partner have no effect on the Peterson/boron‐Wittig chemoselectivity whereas the nature of the silane group plays an important role. A DFT study helps explain observed reactivity, chemoselectivity and stereoseletivity","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"9 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143192193","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
Mannitol‐based CO Surrogate for Palladium‐Catalyzed Alkoxycarbonylation
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1002/ejoc.202401363
Zhen-Wei Liu, Hefei Yang, Zhi-Peng Bao, Jiajun Zhang, Xiao-Feng Wu
{"title":"Mannitol‐based CO Surrogate for Palladium‐Catalyzed Alkoxycarbonylation","authors":"Zhen-Wei Liu, Hefei Yang, Zhi-Peng Bao, Jiajun Zhang, Xiao-Feng Wu","doi":"10.1002/ejoc.202401363","DOIUrl":"https://doi.org/10.1002/ejoc.202401363","url":null,"abstract":"Carbonylative transformation is already been accepted as a powerful toolbox in synthetic chemistry. However, the manipulation of toxic and smell‐less carbon monoxide gas lagged it from wide range applications. Hence the developing of new and efficient CO surrogates become an attractive topic. Herein, we developed a novel mannitol‐based carbon monoxide surrogate with an enhanced carbon monoxide loading capacity compared to known organic carbon monoxide surrogates. We successfully used it in the palladium‐catalyzed alkoxycarbonylation of aryl bromides with phenols only 0.5 equivalent of it required. This newly designed carbon monoxide surrogate offers additional possibility for further development in CO chemistry.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"85 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143192192","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
Recent Advances in the Photochemical Synthesis of Esters
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1002/ejoc.202401398
Jie Li, Da-Liang Zhu, David James Young, Yanqing Wang, Hong-Xi Li
{"title":"Recent Advances in the Photochemical Synthesis of Esters","authors":"Jie Li, Da-Liang Zhu, David James Young, Yanqing Wang, Hong-Xi Li","doi":"10.1002/ejoc.202401398","DOIUrl":"https://doi.org/10.1002/ejoc.202401398","url":null,"abstract":"Photoredox catalysis has recently emerged as a powerful synthetic tool for making a variety of carbon-carbon and carbon-heteroatom bonds. The development of esterification reactions induced by light is an atom economical and energy efficient alternative to traditional methods for the synthesis of esters, with benefits including mild reaction conditions, high chemical yields, and wide functional group tolerance. This review summarizes recent progress made in this green methodology, including mechanisms of action, substrate scope, limitations and future prospects.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"102 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143192371","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
Regioselective Synthesis of n‐Nonanal and Aldehyde‐Containing Polysiloxanes via Rh‐Catalyzed Hydroformylation Enhanced by A New Silicon‐Tethered Multidentate Phosphine Ligand
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1002/ejoc.202500020
Shu-Yuan Tian, Lin Shi, Jun-Hui Zhu, Li Li, Fei Ye, Zheng Xu, Li-Wen Xu
{"title":"Regioselective Synthesis of n‐Nonanal and Aldehyde‐Containing Polysiloxanes via Rh‐Catalyzed Hydroformylation Enhanced by A New Silicon‐Tethered Multidentate Phosphine Ligand","authors":"Shu-Yuan Tian, Lin Shi, Jun-Hui Zhu, Li Li, Fei Ye, Zheng Xu, Li-Wen Xu","doi":"10.1002/ejoc.202500020","DOIUrl":"https://doi.org/10.1002/ejoc.202500020","url":null,"abstract":"Catalytic synthesis of long‐chain alkyl aldehydes presents a significant challenge in homogeneous catalysis and organic synthesis due to the difficulty in regioselective control. Here we report a rhodium‐catalyzed high chemo‐ and regio‐selective hydroformylation of 1‐octene that would be highly useful intermediates in chemical industry. Notably, the easy made tetradentate P‐ligands L1 and L2 can effectively suppress hydrogenation and isomerization reaction of olefins and give the desired aldehydes in high yield and good regioselectivity. Control experiments reveal the tetradentate P‐ligands is important for controlling selectivity because the high regioselectivity is found to benefit from the presence of four phosphorus atoms manifesting in the formation of much more efficient coordination interactions to give relatively stable rhodium complexes.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143192195","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
Amino Acid-Mediated Enantioselective Synthesis of a Bicyclic Ketocarbaldehyde: Theoretical and Experimental Insights into a Key Intermediate for Some Polycyclic Diterpene Synthesis
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-05 DOI: 10.1002/ejoc.202401291
Francesca Leonelli, Fabrizio Vetica, Enrico Bodo, Stefano Russo, Lorenzo Michelini, Elisa Sturabotti, Giulia Mazzoccanti, Alessia Ciogli, Nicola Demitri, Doriano Lamba, Annalisa Masi, Luisa Maria Migneco, Rinaldo Marini Bettolo
{"title":"Amino Acid-Mediated Enantioselective Synthesis of a Bicyclic Ketocarbaldehyde: Theoretical and Experimental Insights into a Key Intermediate for Some Polycyclic Diterpene Synthesis","authors":"Francesca Leonelli, Fabrizio Vetica, Enrico Bodo, Stefano Russo, Lorenzo Michelini, Elisa Sturabotti, Giulia Mazzoccanti, Alessia Ciogli, Nicola Demitri, Doriano Lamba, Annalisa Masi, Luisa Maria Migneco, Rinaldo Marini Bettolo","doi":"10.1002/ejoc.202401291","DOIUrl":"https://doi.org/10.1002/ejoc.202401291","url":null,"abstract":"A study on the amino acid-mediated intramolecular cyclization of diketoaldehyde 2 to form bicyclic ketocarbaldehyde 1, a potentially useful intermediate in the synthesis of some polycyclic diterpenes, is hereafter presented. This cyclization exhibits a peculiar enantio-selectivity if compared to similar intramolecular cyclizations due to its product being the (S)-enantiomer when using d-amino acids. Our findings reveal that the transformation proceeds through two irreversible steps: the cyclization and the subsequent dehydration process. The reaction enantiomeric excess (e.e.) was optimized by systematically varying the amino acids, solvents, and acids used. Aldol intermediates were successfully isolated. The structure of the most abundant one was confirmed by X-ray analysis, which supported the proposed reaction mechanism. NMR and MS were employed to monitor in real-time the formation and the evolution of these intermediates. This approach allowed us to detect the key species that contribute to the enantioselectivity and yield of the final product. Additionally, the transition state energies associated with the formation of the eight possible aldol intermediates were examined through computational studies, further elucidating the mechanistic pathway of this enantioselective cyclization.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"61 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143124959","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
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