Edward Jackman, Oliver Ward, Yi Li, Katie Court, Robert Carroll, Simon Coles, Stephen Beeby, Isabelle Chataigner, Julien Legros, David C. Harrowven
The development of a practicable library synthesis of ionic 2,2'-bifluorenes is described that improves the safety and reduces waste associated with the ubiquitous method of preparing these and related electroluminescent compounds. Additionally, an X-ray crystal structure that reveals how triflate counterions can provide a second link between the alkylimidazolium subunits and the photoluminescent core is presented.
本文介绍了离子型 2,2'-联芴的实用库合成方法，该方法提高了安全性，并减少了与制备这些及相关电致发光化合物的普遍方法有关的浪费。此外，还介绍了一种 X 射线晶体结构，它揭示了三酸盐反离子如何在烷基咪唑鎓亚基和光致发光核心之间提供第二链路。
{"title":"Practicable Syntheses of Electroluminescent Ionic 2,2'-Bifluorenes","authors":"Edward Jackman, Oliver Ward, Yi Li, Katie Court, Robert Carroll, Simon Coles, Stephen Beeby, Isabelle Chataigner, Julien Legros, David C. Harrowven","doi":"10.1002/ejoc.202400976","DOIUrl":"https://doi.org/10.1002/ejoc.202400976","url":null,"abstract":"The development of a practicable library synthesis of ionic 2,2'-bifluorenes is described that improves the safety and reduces waste associated with the ubiquitous method of preparing these and related electroluminescent compounds. Additionally, an X-ray crystal structure that reveals how triflate counterions can provide a second link between the alkylimidazolium subunits and the photoluminescent core is presented.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"18 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142440808","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 have realized the photocatalytic radical cascade cyclization reaction, enabling the one‐step synthesis of rare trifluoroethyl benzopyran derivatives with a wide variety of structures and excellent yields. Furthermore, the approach exhibits low catalyst load, strong regional control and wide applicability under mild conditions. The selectivity of this transformation is influenced by the length of the carbon chain of the benzaldehyde, as demonstrated by the density functional theory calculations. Additionally, scaling up the photocatalytic process can be easily accomplished.
{"title":"Photocatalytic Cascade Trifluoromethylation/Cyclization : Selective Synthesis of Trifluoroethylated Benzopyran and Benzopyranone Derivatives","authors":"Yangjing Lv, Hongmei Luo, Xiaomeng Jiang, Zhichen Yu, Yuxin Ding, Changjun Zhang, Yuanyuan Xie","doi":"10.1002/ejoc.202401013","DOIUrl":"https://doi.org/10.1002/ejoc.202401013","url":null,"abstract":"We have realized the photocatalytic radical cascade cyclization reaction, enabling the one‐step synthesis of rare trifluoroethyl benzopyran derivatives with a wide variety of structures and excellent yields. Furthermore, the approach exhibits low catalyst load, strong regional control and wide applicability under mild conditions. The selectivity of this transformation is influenced by the length of the carbon chain of the benzaldehyde, as demonstrated by the density functional theory calculations. Additionally, scaling up the photocatalytic process can be easily accomplished.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"60 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142439964","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}
An efficient organoiodine-catalysed intramolecular direct C–N bond oxidative coupling reaction is presented. Structurally diverse 3-(mono)substituted oxindoles were rapidly obtained in a complex oxidative system in up to 87% yield. Various N-alkoxy-2-phenylpropanamides were well-tolerated. This study showed that the electronic effects on the aromatic ring of reactants have a crucial effect on the selectivity (C−N/C−O) of cyclisation products. In addition, gram-scale synthesis and late-stage modification of 3-(mono)substituted oxindole derivatives revealed the practical application of this transformation.
{"title":"Organoiodine Catalysed Intramolecular C−N bond Oxidative Coupling for the Synthesis of 3-Monosubstituted Oxindoles","authors":"Yang Wang, Jiang-Ning Yu, Yue Wang, Ji-Chen Yin","doi":"10.1002/ejoc.202400822","DOIUrl":"https://doi.org/10.1002/ejoc.202400822","url":null,"abstract":"An efficient organoiodine-catalysed intramolecular direct C–N bond oxidative coupling reaction is presented. Structurally diverse 3-(mono)substituted oxindoles were rapidly obtained in a complex oxidative system in up to 87% yield. Various N-alkoxy-2-phenylpropanamides were well-tolerated. This study showed that the electronic effects on the aromatic ring of reactants have a crucial effect on the selectivity (C−N/C−O) of cyclisation products. In addition, gram-scale synthesis and late-stage modification of 3-(mono)substituted oxindole derivatives revealed the practical application of this transformation.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"17 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142431570","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}
Yixiong Jia, bin Wen, peiran Nan, huaiyin Chen, Xingquan Chen, Shiyun Li
Dinitroaromatics are valuable organic compounds. However, the high value of these compounds is accompanied by significant risks and formidable challenges. Herein, we report a safe and highly efficient method for the dinitration of various aromatic compounds, using KNO3 as nitrating agent, polyphosphoric acid as solvent and catalyst. This approach provides a safer and more efficient alternative to the traditional mixed acid system, making it suitable for a range of substrates, especially highly deactivated arenes.
{"title":"Polyphosphoric Acid Catalyzed C-H Dinitration of Passivated Aromatic Compounds with Potassium Nitrate under Mild Condition","authors":"Yixiong Jia, bin Wen, peiran Nan, huaiyin Chen, Xingquan Chen, Shiyun Li","doi":"10.1002/ejoc.202401022","DOIUrl":"https://doi.org/10.1002/ejoc.202401022","url":null,"abstract":"Dinitroaromatics are valuable organic compounds. However, the high value of these compounds is accompanied by significant risks and formidable challenges. Herein, we report a safe and highly efficient method for the dinitration of various aromatic compounds, using KNO3 as nitrating agent, polyphosphoric acid as solvent and catalyst. This approach provides a safer and more efficient alternative to the traditional mixed acid system, making it suitable for a range of substrates, especially highly deactivated arenes.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"19 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142431860","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}
Herein, we report a metal and additive-free unprecedented reactivity of β-ketothioamides with sulfonyl chlorides for the synthesis of previously unreported 2-sulfonyl-3-oxo-N,3-diarylpropanamides via in situ thioamide to amide conversion followed by dehydrohalogenative C-S cross-coupling at room temperature under an open air for the first time. The protocol demonstrates not only its operational simplicity, efficiency, mild condition, and scalability, but also easy to get the diverse α-sulfonyl-β-ketoamides in good to high yields. Additionally, the DFT and photophysical studies supported the proposed mechanism, and revealed unique excitation-dependent emission coupled with ESPT for the synthesized sulfones.
{"title":"Metal-Free α-Sulfonylation of β-Ketothioamides: Access to α-Sulfonyl-β-Ketoamides and their Photophysical Studies","authors":"Vipin Kumar, Monish Ansari, Anup Yadav, Saurabh Singh, Krishanu Bandyopadhyay, Satyen Saha, Maya Shankar Singh","doi":"10.1002/ejoc.202401098","DOIUrl":"https://doi.org/10.1002/ejoc.202401098","url":null,"abstract":"Herein, we report a metal and additive-free unprecedented reactivity of β-ketothioamides with sulfonyl chlorides for the synthesis of previously unreported 2-sulfonyl-3-oxo-N,3-diarylpropanamides via in situ thioamide to amide conversion followed by dehydrohalogenative C-S cross-coupling at room temperature under an open air for the first time. The protocol demonstrates not only its operational simplicity, efficiency, mild condition, and scalability, but also easy to get the diverse α-sulfonyl-β-ketoamides in good to high yields. Additionally, the DFT and photophysical studies supported the proposed mechanism, and revealed unique excitation-dependent emission coupled with ESPT for the synthesized sulfones.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"41 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142431569","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}
Yuxuan Cao, Zongxiang Yu, Yizhen Chen, Lu Liu, Yuanjing Xiao
A simple base mediated, highly regioselective 1,4-hydroamidation of β-CF3-1,3-enynamides with secondary amides for synthesis of tri-substituted γ-CF3-allenamides compounds was developed. N-alkyl sulfonamides are generally good candidates for the present transformation. γ-CF3-allenamides could be employed for synthesis of potential value-added compounds such as fluorinated halogenated pyrrole, tetrahydroquinoline and 2-CF3-putrescine derivatives.
{"title":"Regioselective Intermolecular Hydroamidation of β-CF3-1,3-enynamides: An Approach to Tri-substituted γ-CF3-allenamides","authors":"Yuxuan Cao, Zongxiang Yu, Yizhen Chen, Lu Liu, Yuanjing Xiao","doi":"10.1002/ejoc.202400674","DOIUrl":"https://doi.org/10.1002/ejoc.202400674","url":null,"abstract":"A simple base mediated, highly regioselective 1,4-hydroamidation of β-CF3-1,3-enynamides with secondary amides for synthesis of tri-substituted γ-CF3-allenamides compounds was developed. N-alkyl sulfonamides are generally good candidates for the present transformation. γ-CF3-allenamides could be employed for synthesis of potential value-added compounds such as fluorinated halogenated pyrrole, tetrahydroquinoline and 2-CF3-putrescine derivatives.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"2 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142431564","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}
Bruno Salgues, Rudraditya Sarkar, Nans Potier, Anne-Doriane Manick, Gabriel Canard, Jean-Luc Parrain, Michel Giorgi, Nicolas Vanthuyne, Christine Videlot-Ackermann, Jorg Ackermann, Frédéric Fages, Boris Le Guennic, Denis Jacquemin, Muriel Amatore, Elena Zaborova, Laurent Commeiras
The synthesis and the studies of optical and electronic properties of new bis-indenone-fused tetraazaanthracene isomers as electron accepting materials are reported. TD-DFT calculations have been also undertaken and corroborate experiments. Organic field effect transistors demonstrated unipolar n-type characteristics and average electron mobility values.
报告了作为电子接受材料的新型双茚酮融合四氮杂蒽异构体的合成及其光学和电子特性研究。此外，还进行了 TD-DFT 计算，并与实验相互印证。有机场效应晶体管显示了单极 n 型特性和平均电子迁移率值。
{"title":"Bis-Indeno-Fused Tetraazaanthracene Hybrids: Straightforward Synthesis and Studies of Optical and Electronic Properties","authors":"Bruno Salgues, Rudraditya Sarkar, Nans Potier, Anne-Doriane Manick, Gabriel Canard, Jean-Luc Parrain, Michel Giorgi, Nicolas Vanthuyne, Christine Videlot-Ackermann, Jorg Ackermann, Frédéric Fages, Boris Le Guennic, Denis Jacquemin, Muriel Amatore, Elena Zaborova, Laurent Commeiras","doi":"10.1002/ejoc.202400719","DOIUrl":"https://doi.org/10.1002/ejoc.202400719","url":null,"abstract":"The synthesis and the studies of optical and electronic properties of new bis-indenone-fused tetraazaanthracene isomers as electron accepting materials are reported. TD-DFT calculations have been also undertaken and corroborate experiments. Organic field effect transistors demonstrated unipolar n-type characteristics and average electron mobility values.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"123 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142431567","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 direct asymmetric vinylogous allylic alkylation is an efficient method to construct chiral 1,5-diene compounds. In this work, acyclic unsaturated amides are used as a nucleophile for enantioselective vinylogous allylic alkylation. With 10 mol% of chiral tertiary amine C11, the enantioselective vinylogous allylic alkylation between β,γ-unsaturated pyrazoleamides and Morita-Baylis-Hillman carbonates is achieved, affording optically active multifunctional chiral 1,5-dienes in moderate to excellent yields (74-99%) with good-to-excellent enantioselectivities (67-94% ee).
{"title":"Organocatalytic Enantioselective Vinylogous Allylic Alkylation between β,γ-Unsaturated Pyrazoleamides and MBH Carbonates","authors":"Yun-Peng He, Jun-Hao Fu, Feng Sha, Xin-Yan Wu","doi":"10.1002/ejoc.202400799","DOIUrl":"https://doi.org/10.1002/ejoc.202400799","url":null,"abstract":"The direct asymmetric vinylogous allylic alkylation is an efficient method to construct chiral 1,5-diene compounds. In this work, acyclic unsaturated amides are used as a nucleophile for enantioselective vinylogous allylic alkylation. With 10 mol% of chiral tertiary amine C11, the enantioselective vinylogous allylic alkylation between β,γ-unsaturated pyrazoleamides and Morita-Baylis-Hillman carbonates is achieved, affording optically active multifunctional chiral 1,5-dienes in moderate to excellent yields (74-99%) with good-to-excellent enantioselectivities (67-94% ee).","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"2 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142431568","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}
An additive-free and diastereoselective [4 + 1] annulation between ortho-hydroxyphenyl-substituted para-quinone methides and CF3-substituted imidoyl sulfoxonium ylides is developed, providing a facile and practical route to diverse trans-2,3-dihydrobenzofurans with high efficiency. This protocol features mild conditions, broad substrate scope and easy to operate.
{"title":"Additive-free and Diastereoselective Synthesis for trans-Disubstituted-2,3-dihydro-benzofurans via [4 + 1] Annulation between p-QMs and TFISYs","authors":"Yi-Hui Li, Chuan-Chuan Wang, Meng-Ru Ren, Qing-Long Wang, Ya-Jing Chen","doi":"10.1002/ejoc.202400946","DOIUrl":"https://doi.org/10.1002/ejoc.202400946","url":null,"abstract":"An additive-free and diastereoselective [4 + 1] annulation between ortho-hydroxyphenyl-substituted para-quinone methides and CF3-substituted imidoyl sulfoxonium ylides is developed, providing a facile and practical route to diverse trans-2,3-dihydrobenzofurans with high efficiency. This protocol features mild conditions, broad substrate scope and easy to operate.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"2 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142431563","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}
Priyanka Choudhary, Ravikant S. Ranjan, Rodney Fernandes
This work reports a Cu-catalyzed coupling technique for synthesizing (E)-dienyl sulfones and β-chlorosulfones from 1-arylbutadienes and styrenes, respectively. By employing easily available and inexpensive reagents, this method enables the synthesis of a diverse array of dienyl sulfones and β-chlorosulfones with excellent functional group tolerance under base- and oxidant-free conditions. It also proves versatile for the late-stage functionalization of drug molecules and the scale-up reactions. The method showcases notable selectivity, gentle reaction conditions, and compatibility with various functional groups as demonstrated through 66 examples with excellent display of regioselectivity.
{"title":"Cu-Catalyzed Coupling of Sulfonyl Chlorides with Alkenes: Synthesis of Dienyl Sulfones and β-Chlorosulfones","authors":"Priyanka Choudhary, Ravikant S. Ranjan, Rodney Fernandes","doi":"10.1002/ejoc.202401077","DOIUrl":"https://doi.org/10.1002/ejoc.202401077","url":null,"abstract":"This work reports a Cu-catalyzed coupling technique for synthesizing (E)-dienyl sulfones and β-chlorosulfones from 1-arylbutadienes and styrenes, respectively. By employing easily available and inexpensive reagents, this method enables the synthesis of a diverse array of dienyl sulfones and β-chlorosulfones with excellent functional group tolerance under base- and oxidant-free conditions. It also proves versatile for the late-stage functionalization of drug molecules and the scale-up reactions. The method showcases notable selectivity, gentle reaction conditions, and compatibility with various functional groups as demonstrated through 66 examples with excellent display of regioselectivity.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142431560","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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