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Journal of Fluorine Chemistry最新文献

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6-Polyfluoroalkyl-1-arylhexane-1,3,5-triones: Syntheses, ring-chain tautomerism and dehydrative cyclization to 6-polyfluoroalkyl-1-arylpyran-4H-ones 6-多氟烷基-1-芳基己烷-1,3,5-三酮：合成、环链同分异构和脱水环化为 6-多氟烷基-1-芳基吡喃-4H-酮
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-11-01 DOI: 10.1016/j.jfluchem.2024.110368
Ivan A. Kochnev, Lyudmila S. Zavyalova, Azaliia I. Avkhadieva, Nikolay A. Tverdokhlebov, Alexey Y. Barkov
{"title":"6-Polyfluoroalkyl-1-arylhexane-1,3,5-triones: Syntheses, ring-chain tautomerism and dehydrative cyclization to 6-polyfluoroalkyl-1-arylpyran-4H-ones","authors":"Ivan A. Kochnev,&nbsp;Lyudmila S. Zavyalova,&nbsp;Azaliia I. Avkhadieva,&nbsp;Nikolay A. Tverdokhlebov,&nbsp;Alexey Y. Barkov","doi":"10.1016/j.jfluchem.2024.110368","DOIUrl":"10.1016/j.jfluchem.2024.110368","url":null,"abstract":"<div><div>In this work, we present a synthetic protocol for the synthesis of non-symmetrical fluoroalkylated triketones. The synthesis is based on the reaction of benzoyl acetones with esters in the presence of excess lithium hydride. The tautomeric equilibrium of triketones in CDCl<sub>3</sub> and DMSO‑<em>d</em><sub>6</sub> solutions was studied. The synthetic application of 1,3,5-triketones has been demonstrated. A method has been developed for the efficient synthesis of 2-aryl-6-(polyfluoroalkyl)-4<em>H</em>-pyran-4-ones by dehydrative cyclization.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"280 ","pages":"Article 110368"},"PeriodicalIF":1.7,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142660305","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Controlled nucleophilic aromatic substitution of hexafluorobenzene using a flow microreactor 利用流动微反应器控制六氟苯的亲核芳香取代反应
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-11-01 DOI: 10.1016/j.jfluchem.2024.110366
Aya Takano, Fuji Saito, Hiroyuki Murata, Tsuyuka Sugiishi, Hideki Amii
{"title":"Controlled nucleophilic aromatic substitution of hexafluorobenzene using a flow microreactor","authors":"Aya Takano,&nbsp;Fuji Saito,&nbsp;Hiroyuki Murata,&nbsp;Tsuyuka Sugiishi,&nbsp;Hideki Amii","doi":"10.1016/j.jfluchem.2024.110366","DOIUrl":"10.1016/j.jfluchem.2024.110366","url":null,"abstract":"<div><div>Nucleophilic aromatic substitution (S<sub>N</sub>Ar) contributes to creating a variety of useful materials. It is well-known that selective S<sub>N</sub>Ar reactions of perfluorinated aromatics such as hexafluorobenzene with nucleophiles are difficult to achieve using conventional macro batch systems due to the contamination of the di-substituted products. To take advantage of flow microreactor system, we succeeded in the controlled S<sub>N</sub>Ar reactions of hexafluorobenzene with organolithiums employing continuous flow reactors.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"280 ","pages":"Article 110366"},"PeriodicalIF":1.7,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142554884","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
Corrosion of iron in liquid uranium hexafluoride at 80 °C. Part I: Normal and abnormal experimental kinetics 铁在 80 °C 的液态六氟化铀中的腐蚀。第一部分：正常和异常实验动力学
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-11-01 DOI: 10.1016/j.jfluchem.2024.110370
Mickaël Achour , Sylvie Chatain , Laure Martinelli , Fréderic Miserque , Laurent Jouffret , Marc Dubois , Pierre Bonnet , Ania Selmi , Lionel Mazellier , Bertrand Morel , Sylvie Delpech
{"title":"Corrosion of iron in liquid uranium hexafluoride at 80 °C. Part I: Normal and abnormal experimental kinetics","authors":"Mickaël Achour ,&nbsp;Sylvie Chatain ,&nbsp;Laure Martinelli ,&nbsp;Fréderic Miserque ,&nbsp;Laurent Jouffret ,&nbsp;Marc Dubois ,&nbsp;Pierre Bonnet ,&nbsp;Ania Selmi ,&nbsp;Lionel Mazellier ,&nbsp;Bertrand Morel ,&nbsp;Sylvie Delpech","doi":"10.1016/j.jfluchem.2024.110370","DOIUrl":"10.1016/j.jfluchem.2024.110370","url":null,"abstract":"<div><div>The results reported here are the first on pure iron corrosion in liquid UF<sub>6</sub> at 80 °C. Two kinetic behaviours have been observed: one led to micrometric scales (from micron to hundreds of microns after several months) and the other one to hundreds of nanometers for several months. The higher corrosion kinetics resulted in the presence of impurities such as NO<sub>x</sub>F complexes formed by interaction between the medium and the reactor material. These NO<sub>x</sub>F catalysed the corrosion reaction leading to a corrosion mechanism controlled by the cathodic reaction rate. Effect of impurities in UF<sub>6</sub> coming from experimental conditions or nature of uranium ore should then be systematically and carefully checked. Whatever the corrosion kinetics and the presence of impurities, the nature of the layer was identical: a duplex fluoride scale composed of an iron rich layer, FeF<sub>2</sub>, and a uranium rich layer evolving over time from U<sub>2</sub>F<sub>9</sub> to UF<sub>5</sub>.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"280 ","pages":"Article 110370"},"PeriodicalIF":1.7,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142660304","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Oligoacrylates with perfluoroalkyl substituents based on hexafluoropropylene trimer as environment friendly hydrophobic coatings 基于六氟丙烯三聚体的具有全氟烷基取代基的寡聚丙烯酸酯作为环保型疏水性涂料
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-11-01 DOI: 10.1016/j.jfluchem.2024.110369
P.D. Shkinev , M.I. Shagidanova , G.V. Cherkaev , F.V. Drozdov
{"title":"Oligoacrylates with perfluoroalkyl substituents based on hexafluoropropylene trimer as environment friendly hydrophobic coatings","authors":"P.D. Shkinev ,&nbsp;M.I. Shagidanova ,&nbsp;G.V. Cherkaev ,&nbsp;F.V. Drozdov","doi":"10.1016/j.jfluchem.2024.110369","DOIUrl":"10.1016/j.jfluchem.2024.110369","url":null,"abstract":"<div><div>The most effective classes of polymer water repellents include acrylic polymer with perfluoroalkyl additives. However, due to the prohibition of substances with a long perfluoroalkyl linear chain longer than 6 carbon atoms by the Stockholm Convention on Persistent Organic Pollutants, there is a significant necessity to replace them with approved analogues. This work considered substituted acrylates based on commercially available hexafluoropropylene trimer and their polymerization in a supercritical CO<sub>2</sub> medium as the most convenient way and the hydrophobizing ability on various types of surfaces. The contact angles of the coatings obtained based on these oligomers are up to 111 ° on glass and aluminum, and 130 ° on cotton fabric, which is comparable to analogs with linear perfluoroalkyl substituents.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"280 ","pages":"Article 110369"},"PeriodicalIF":1.7,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142561249","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
FeCl3⋅6H2O-mediated cyclization of fluorinated 2’-hydroxychalcones in alcohol medium into flavanones with antiviral activity FeCl3⋅6H2O介导的氟化2'-羟基查耳酮在酒精介质中环化成具有抗病毒活性的黄烷酮类化合物
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-11-01 DOI: 10.1016/j.jfluchem.2024.110371
Jiaying Wang , Larisa Politanskaya , Boris Selivanov , Iana Esaulkova , Alexandrina Volobueva , Vladimir Zarubaev
{"title":"FeCl3⋅6H2O-mediated cyclization of fluorinated 2’-hydroxychalcones in alcohol medium into flavanones with antiviral activity","authors":"Jiaying Wang ,&nbsp;Larisa Politanskaya ,&nbsp;Boris Selivanov ,&nbsp;Iana Esaulkova ,&nbsp;Alexandrina Volobueva ,&nbsp;Vladimir Zarubaev","doi":"10.1016/j.jfluchem.2024.110371","DOIUrl":"10.1016/j.jfluchem.2024.110371","url":null,"abstract":"<div><div>A simple, inexpensive and efficient approach for the synthesis of fluorinated 2-arylchroman-4-ones from corresponding 2′-hydroxychalcones has been realized. The reactions are successfully conducted in presence of FeCl<sub>3</sub>⋅6H<sub>2</sub>O in EtOH at 100 °C. It was found that the same transformation takes place in the reaction system FeCl<sub>3</sub>⋅6H<sub>2</sub>O/MeOH/100 °C. In contrast, the use of FeCl<sub>3</sub>⋅6H<sub>2</sub>O in MeOH at 150 °C leads to the oxidative cyclization of 2′-hydroxychalcones to form 2-arylchromen-4-ones. A some of the obtained fluorinated flavanones were evaluated for their inhibitory activity against influenza A virus A/Puerto Rico/8/34 (H1N1) in the MDCK cell culture. Among the studied heterocycles 6,7-difluoro-2-(4-methoxyphenyl)chroman-4-one exhibited the highest anti-influenza virus activity (IC<sub>50</sub> = 11.4 μM, SI = 91).</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"280 ","pages":"Article 110371"},"PeriodicalIF":1.7,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142699340","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Two F-18 radiochemistry methods to synthesize a promising transient receptor potential canonical 5 (TRPC5) radioligand 用两种 F-18 放射化学方法合成有前景的瞬态受体电位 5 (TRPC5) 放射配体
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-10-22 DOI: 10.1016/j.jfluchem.2024.110367
Yanbo Yu , Sandip B. Jadhav , Zhimin Xing , Hao Jiang , Lin Qiu , Tianyu Huang , Joel S. Perlmutter , Zibo Li , Zhude Tu
{"title":"Two F-18 radiochemistry methods to synthesize a promising transient receptor potential canonical 5 (TRPC5) radioligand","authors":"Yanbo Yu ,&nbsp;Sandip B. Jadhav ,&nbsp;Zhimin Xing ,&nbsp;Hao Jiang ,&nbsp;Lin Qiu ,&nbsp;Tianyu Huang ,&nbsp;Joel S. Perlmutter ,&nbsp;Zibo Li ,&nbsp;Zhude Tu","doi":"10.1016/j.jfluchem.2024.110367","DOIUrl":"10.1016/j.jfluchem.2024.110367","url":null,"abstract":"<div><div>TRPC5 is a member of the mammalian transient receptor potential (TRP) channel superfamily and it has been implicated in various physiological and pathological mechanisms of neurological and psychiatric diseases. Fluorine-18 is one of the most widely used radionuclides for PET imaging due to its favorable chemical characteristics and nuclear-physical properties. Herein, we describe two complementary radiosynthetic approaches and preliminary <em>in vivo</em> evaluation for [<sup>18</sup>F]<strong>TZ78141</strong> as a novel and promising fluorine-18 labeled radiotracer for imaging TRPC5. The latter strategy employed a ruthenium-mediated radiofluorination method, facilitating the rapid synthesis of the desired radiotracer with substantial advantages in simplicity and efficiency.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"280 ","pages":"Article 110367"},"PeriodicalIF":1.7,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142527122","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
The synthesis of N-Trifluoromethyl hydroxylamine from (trifluoromethyl)trimethylsilane 从（三氟甲基）三甲基硅烷合成 N-三氟甲基羟胺
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-10-16 DOI: 10.1016/j.jfluchem.2024.110356
Haixia Song, Qin Wang, Xingjie Ruan, Weilong Hu, Le Liu, Xin-Hua Duan, Mingyou Hu
{"title":"The synthesis of N-Trifluoromethyl hydroxylamine from (trifluoromethyl)trimethylsilane","authors":"Haixia Song,&nbsp;Qin Wang,&nbsp;Xingjie Ruan,&nbsp;Weilong Hu,&nbsp;Le Liu,&nbsp;Xin-Hua Duan,&nbsp;Mingyou Hu","doi":"10.1016/j.jfluchem.2024.110356","DOIUrl":"10.1016/j.jfluchem.2024.110356","url":null,"abstract":"<div><div>We have presented a straightforward approach for the synthesis of <em>N</em>-CF<sub>3</sub> hydroxylamines, utilizing TMSCF<sub>3</sub> for the <em>N</em>-trifluoromethylation of nitrosoarenes with the assistance of CsF. This method demonstrates excellent tolerance towards various functional groups and can be applied to a wide range of substrates, highlighting its versatility and utility in synthetic applications. The nucleophilic <em>N</em>-trifluoromethylation pathway for <em>N</em>-CF<sub>3</sub> hydroxylamines provides a practical protocol for the synthesis of promising molecular architectures in the field of medicinal chemistry.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"280 ","pages":"Article 110356"},"PeriodicalIF":1.7,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142527123","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 4-fluoroisocoumarins by copper-catalyzed annulation of 2-halobenzoic acids and 2-fluoro-1,3-diketones 铜催化 2-卤苯甲酸和 2-氟-1,3-二酮环化合成 4-氟异香豆素
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-10-09 DOI: 10.1016/j.jfluchem.2024.110355
Haruki Sakagami, Akira Tsubouchi, Akio Saito
{"title":"Synthesis of 4-fluoroisocoumarins by copper-catalyzed annulation of 2-halobenzoic acids and 2-fluoro-1,3-diketones","authors":"Haruki Sakagami,&nbsp;Akira Tsubouchi,&nbsp;Akio Saito","doi":"10.1016/j.jfluchem.2024.110355","DOIUrl":"10.1016/j.jfluchem.2024.110355","url":null,"abstract":"<div><div>Fluorinated heterocycles have been promising in the field of medicinal, agrochemical and materials chemistry due to their unique properties. However, despite the potentially very useful structures of fluorinated isocoumarins, the synthetic method of fluorinated isocoumarins remains a challenging topic. Herein, we describe the synthetic method of fluorinated isocoumarins by tandem coupling-cyclization-deacylation reaction of readily available 2-halobenzoic acids and 2-fluoro-1,3-diketones. This study provides one of the few synthetic methods of fluorinated isocoumarins.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"280 ","pages":"Article 110355"},"PeriodicalIF":1.7,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142445557","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
CF3S-N bond formation under mild conditions. Easy access to trifluoromethanesulfenamides with a versatile reagent 在温和条件下形成 CF3S-N 键。利用多功能试剂轻松获得三氟甲磺酰胺
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-10-01 DOI: 10.1016/j.jfluchem.2024.110353
Clément Delobel , Fabien Toulgoat , Thierry Billard
{"title":"CF3S-N bond formation under mild conditions. Easy access to trifluoromethanesulfenamides with a versatile reagent","authors":"Clément Delobel ,&nbsp;Fabien Toulgoat ,&nbsp;Thierry Billard","doi":"10.1016/j.jfluchem.2024.110353","DOIUrl":"10.1016/j.jfluchem.2024.110353","url":null,"abstract":"<div><div>Trifluoromethanesulfenamides (CF<sub>3</sub>SN-molecules) are interesting products for further applications. In particular, the presence of the CF<sub>3</sub>SN group can contribute to increase their lipophilicity. The better way to obtain such products is the direct trifluoromethylthiolation of the corresponding amines. Herein, an efficient method under mild conditions (room temperature, iodide catalysis) is described to obtain the expected trifluoromethanesulfenamides in a late-stage functionalization. This method is based on the use of the reagent <strong>BB23</strong> (<em>N</em>-tosyl, <em>N</em>-methyltrifluoromethanesulfenamide), demonstrating the high versatility and polyvalence of this reagent in organofluorine chemistry. Some bioactive elaborated compounds were successfully functionalized.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"279 ","pages":"Article 110353"},"PeriodicalIF":1.7,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142424967","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
The perfluoroalkylthiolation reaction of thiols with perfluoroalkanesulfenic acids 硫醇与全氟烷基亚磺酸的全氟烷基硫代反应
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-10-01 DOI: 10.1016/j.jfluchem.2024.110354
Ye-lin Liu , Xiao-Yu Geng , Min Jiang , Jin-Tao Liu
{"title":"The perfluoroalkylthiolation reaction of thiols with perfluoroalkanesulfenic acids","authors":"Ye-lin Liu ,&nbsp;Xiao-Yu Geng ,&nbsp;Min Jiang ,&nbsp;Jin-Tao Liu","doi":"10.1016/j.jfluchem.2024.110354","DOIUrl":"10.1016/j.jfluchem.2024.110354","url":null,"abstract":"<div><div>The perfluoroalkylthiolation reactions of thiols with perfluoroalkanesulfenic acids were achieved without adding any additives, giving a series of unsymmetric disulfides in good to excellent yields. After simple removal of solvent from reaction system under reduced pressure, most products could be obtained with high purity. The reaction tolerates both aryl and alkyl thiols and has advantages such as easy-to-handle, additive-free and simple separation procedure.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"279 ","pages":"Article 110354"},"PeriodicalIF":1.7,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142424968","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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