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Journal of Fluorine Chemistry最新文献

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(2S)-2-(Difluoro(methoxy)methyl)pyrrolidine-1-sulfinyl fluoride as a new reagent in the Cl/F exchange reactions with aryl and alkyl sulfonyl chlorides (2S)-2-(二氟(甲氧基)甲基)吡咯烷-1-亚磺酰氟作为与芳基和烷基磺酰氯进行 Cl/F 交换反应的新试剂
IF 1.9 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-05-01 DOI: 10.1016/j.jfluchem.2024.110293
Sergiy V. Zasukha , Alexander B. Rozhenko , Yuriy G. Shermolovich
{"title":"(2S)-2-(Difluoro(methoxy)methyl)pyrrolidine-1-sulfinyl fluoride as a new reagent in the Cl/F exchange reactions with aryl and alkyl sulfonyl chlorides","authors":"Sergiy V. Zasukha ,&nbsp;Alexander B. Rozhenko ,&nbsp;Yuriy G. Shermolovich","doi":"10.1016/j.jfluchem.2024.110293","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2024.110293","url":null,"abstract":"<div><p>The reaction of (<em>2S</em>)-2-(difluoro(methoxy)methyl)pyrrolidine-1-sulfinyl fluoride with aryl, heteryl and alkyl sulfonyl chlorides provides a convenient synthetic route to sulfonyl fluorides. DFT calculations predict negative reaction energy values for the exchange reaction. The S-F bond energy is higher in the sulfonyl fluorides than that in sulfinyl fluorides.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"276 ","pages":"Article 110293"},"PeriodicalIF":1.9,"publicationDate":"2024-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140823974","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
Visible-light-induced photocatalytic iododi(per)fluoroalkylation of 5-amino-N-allyl-1,2,3-triazole-4-carboxamides 可见光诱导的 5-氨基-N-烯丙基-1,2,3-三唑-4-甲酰胺碘（过）氟烷基化光催化反应
IF 1.9 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-04-24 DOI: 10.1016/j.jfluchem.2024.110292
Ivanna Yu. Danyliuk , Sergiy V. Kemskyi , Vladyslav M. Polishchuk , Svitlana V. Shishkina , Mykhailo V. Vovk
{"title":"Visible-light-induced photocatalytic iododi(per)fluoroalkylation of 5-amino-N-allyl-1,2,3-triazole-4-carboxamides","authors":"Ivanna Yu. Danyliuk ,&nbsp;Sergiy V. Kemskyi ,&nbsp;Vladyslav M. Polishchuk ,&nbsp;Svitlana V. Shishkina ,&nbsp;Mykhailo V. Vovk","doi":"10.1016/j.jfluchem.2024.110292","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2024.110292","url":null,"abstract":"<div><p>Readily available di(per)fluoroalkyl iodides and ethyl difluoroiodoacetate have been efficiently reacted with 5-amino-<em>N</em>-allyl-1,2,3-triazole-4-carboxamides in the presence of DIPEA under visible-light induction and fluorescein catalysis to produce high yields of the corresponding adducts, <em>N</em>-(<em>n</em>-propyl) carboxamides vicinally difunctionalized with the iodine atom and the di(per)fluoroalkyl or (methoxycarbonyl)difluoromethyl moiety. As shown experimentally, this regiospecific and triazole amino group tolerant reaction involves a radical process.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"276 ","pages":"Article 110292"},"PeriodicalIF":1.9,"publicationDate":"2024-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140643541","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
Unexpected reaction of antimony pentafluoride with a fluorinated propellane 五氟化锑与含氟推进烷的意外反应
IF 1.9 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-04-13 DOI: 10.1016/j.jfluchem.2024.110281
Matthias Bremer
{"title":"Unexpected reaction of antimony pentafluoride with a fluorinated propellane","authors":"Matthias Bremer","doi":"10.1016/j.jfluchem.2024.110281","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2024.110281","url":null,"abstract":"<div><p>While 1,3-dehydro-5,7-difluoroadamantane <strong>11</strong> reacts with SbF<sub>5</sub> in super acid media (SO<sub>2</sub>ClF) to generate the 1,3-dehydroadamant-5,7-diyl dication <strong>1</strong>, 1,3-dehydro-5-fluoroadamantane <strong>12</strong> fails to react analogously to produce the 1,3-dehydroadamant-5-yl cation <strong>9</strong>; instead, the 3,5-difluoro-1-adamantylcation <strong>13</strong> is formed. We present a computational study that explains this surprising behavior by the initial addition of Sb<sub>2</sub>F<sub>10</sub> to the propellane bond present in <strong>12</strong>. This is computed to be highly exothermic and leads to a zwitterionic (or ion-pair) species, which in turn reacts autocatalytically with HF to produce the observed fluorinated cation <strong>13</strong>, SbF<sub>3</sub>, and SbF<sub>6</sub><sup>–</sup>.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"276 ","pages":"Article 110281"},"PeriodicalIF":1.9,"publicationDate":"2024-04-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0022113924000411/pdfft?md5=14094f767e6d9d02c80729ea51095d21&pid=1-s2.0-S0022113924000411-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140551631","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
Mild synthesis of 2,3,5,6-tetrafluoropyridine ethers and their reactivity toward imidazole and pyrazole 2,3,5,6-四氟吡啶醚的温和合成及其对咪唑和吡唑的反应活性
IF 1.9 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-04-06 DOI: 10.1016/j.jfluchem.2024.110280
Nathan J. Weeks , Kyle D. Kramer , Nicholas W. Surina , Timothy J. Fuhrer , Scott T. Iacono
{"title":"Mild synthesis of 2,3,5,6-tetrafluoropyridine ethers and their reactivity toward imidazole and pyrazole","authors":"Nathan J. Weeks ,&nbsp;Kyle D. Kramer ,&nbsp;Nicholas W. Surina ,&nbsp;Timothy J. Fuhrer ,&nbsp;Scott T. Iacono","doi":"10.1016/j.jfluchem.2024.110280","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2024.110280","url":null,"abstract":"<div><p>A series of six, 4-substituted 2,3,5,6-tetrafluoropyridine (TFP) hetero ethers have been synthesized via regio-selective, nucleophilic aromatic substitution (SNAr) of pentafluoropyridine with aliphatic alcohols and phenols. Furthermore, the hexyloxy modified TFP substrate also served as a synthetic intermediate for the preparation of 3,5-difluoro-4-(hexyloxy)-2,6-di(<em>1H</em>-imidazol-1-yl)pyridine, as well as 4-(hexyloxy)-2,3,5,6-tetra(<em>1H</em>-pyrazol-1-yl)pyridine, which offers a terpyridine scaffold. This work outlines their synthetic methodology in addition to detailing the TFP intermediates’ unexpected reactivity with imidazole and pyrazole nucleophiles</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"276 ","pages":"Article 110280"},"PeriodicalIF":1.9,"publicationDate":"2024-04-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140545894","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
Syntheses of α-monofluoroalkyl acetophenones from fluoroalkyl carboxylic NHPI esters and silyl enol ethers by photocatalytic decarboxylative reaction 通过光催化脱羧反应从氟烷基羧基 NHPI 酯和硅基醚合成 α-单氟烷基苯乙酮
IF 1.9 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-04-04 DOI: 10.1016/j.jfluchem.2024.110279
Min Kou , Jianli Zheng , Tong Chen , Yanghao Wu , Ling Huang , Dongdong Cao , Dingben Chen
{"title":"Syntheses of α-monofluoroalkyl acetophenones from fluoroalkyl carboxylic NHPI esters and silyl enol ethers by photocatalytic decarboxylative reaction","authors":"Min Kou ,&nbsp;Jianli Zheng ,&nbsp;Tong Chen ,&nbsp;Yanghao Wu ,&nbsp;Ling Huang ,&nbsp;Dongdong Cao ,&nbsp;Dingben Chen","doi":"10.1016/j.jfluchem.2024.110279","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2024.110279","url":null,"abstract":"<div><p>A photoredox-catalyzed decarboxylative α-monofluoroalkylation of silyl enol ethers with fluoroalkyl carboxylic N-(hydroxy)phthalimide esters has been successfully developed. Diverse functionalized α-monofluoroalkyl acetophenones were produced in modest to good yields under mild and operationally simple conditions. The developed method was further applied to synthesize antalgic and ataractic activity compound containing α-monofluoroalkyl acetophenone skeleton.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"276 ","pages":"Article 110279"},"PeriodicalIF":1.9,"publicationDate":"2024-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140540508","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
Obituary — Professor Dr. Boris Žemva 讣告 - 鲍里斯-热姆瓦博士教授
IF 1.9 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-04-01 DOI: 10.1016/j.jfluchem.2024.110262
Hélène H.P.A. Mercier , Kristian Radan , Gary J. Schrobilgen
{"title":"Obituary — Professor Dr. Boris Žemva","authors":"Hélène H.P.A. Mercier ,&nbsp;Kristian Radan ,&nbsp;Gary J. Schrobilgen","doi":"10.1016/j.jfluchem.2024.110262","DOIUrl":"10.1016/j.jfluchem.2024.110262","url":null,"abstract":"","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"275 ","pages":"Article 110262"},"PeriodicalIF":1.9,"publicationDate":"2024-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139948661","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 gem‑bromofluoroolefins using singlet bromofluorocarbene generated from ethyl dibromofluoroacetate via a Wittig-type reaction 利用通过 Wittig 型反应从乙基二溴氟乙酸酯生成的单质溴氟羰基合成 gem-bromofluoroolefins
IF 1.9 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-03-30 DOI: 10.1016/j.jfluchem.2024.110278
Matthew Coe , Fanni Bede , Christopher J． Koch, Danelle Daria Espiritu , G．K．Surya Prakash
{"title":"Synthesis of gem‑bromofluoroolefins using singlet bromofluorocarbene generated from ethyl dibromofluoroacetate via a Wittig-type reaction","authors":"Matthew Coe ,&nbsp;Fanni Bede ,&nbsp;Christopher J． Koch,&nbsp;Danelle Daria Espiritu ,&nbsp;G．K．Surya Prakash","doi":"10.1016/j.jfluchem.2024.110278","DOIUrl":"10.1016/j.jfluchem.2024.110278","url":null,"abstract":"<div><p>A halon-free method for the synthesis of <em>gem</em>‑bromofluoroolefins utilizing ethyldibromofluoro-acetate is disclosed via a Wittig type reaction. The reaction system takes advantage of inexpensive and readily available reagents. The method was applied to a wide variety of aryl aldehydes. Both electron donating and electron withdrawing moieties on the aryl ring were tolerated and the desired olefin products were obtained in good to excellent yields.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"276 ","pages":"Article 110278"},"PeriodicalIF":1.9,"publicationDate":"2024-03-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140400769","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 anhydrous cerium tetrafluoride 无水四氟化铈的合成
IF 1.9 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-03-28 DOI: 10.1016/j.jfluchem.2024.110275
Maria N. Brekhovskikh , Leonid A. Vaimugin , Liudmila V. Moiseeva , Liudmila I. Demina , Konstantin S. Nikonov , Vladislav E. Shukshin
{"title":"Synthesis of anhydrous cerium tetrafluoride","authors":"Maria N. Brekhovskikh ,&nbsp;Leonid A. Vaimugin ,&nbsp;Liudmila V. Moiseeva ,&nbsp;Liudmila I. Demina ,&nbsp;Konstantin S. Nikonov ,&nbsp;Vladislav E. Shukshin","doi":"10.1016/j.jfluchem.2024.110275","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2024.110275","url":null,"abstract":"<div><p>By reacting CeF<sub>3</sub> with XeF<sub>2</sub> the anhydrous CeF<sub>4</sub> was synthesized and studied by XRD, SEM, FTIR, <sup>19</sup>F NMR spectrometry and thermogravimetry. It was found that CeF<sub>4</sub> undergoes hydration upon keeping in air forming the crystalline hydrate with the approximate formula [CeF<sub>4</sub>•0.2H<sub>2</sub>O]*0.7H<sub>2</sub>O. Water molecules both enter the coordination sphere of cerium and form crystalline hydrates with cerium(IV) fluoride due to OH…F hydrogen bonds in the crystal lattice.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"275 ","pages":"Article 110275"},"PeriodicalIF":1.9,"publicationDate":"2024-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140308857","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
Ex-situ ChloGen: A facile and straightforward entry to Aryl-IF4 compounds 原位 ChloGen：简单直接地进入芳基-IF4化合物
IF 1.9 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-03-27 DOI: 10.1016/j.jfluchem.2024.110276
Karim Ullah , Reza Kordnezhadian , Joachim Demaerel , Wim M. De Borggraeve , Ermal Ismalaj
{"title":"Ex-situ ChloGen: A facile and straightforward entry to Aryl-IF4 compounds","authors":"Karim Ullah ,&nbsp;Reza Kordnezhadian ,&nbsp;Joachim Demaerel ,&nbsp;Wim M. De Borggraeve ,&nbsp;Ermal Ismalaj","doi":"10.1016/j.jfluchem.2024.110276","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2024.110276","url":null,"abstract":"<div><p>In this work, we present a new method for the facile preparation of aryl-IF<sub>4</sub> compounds using KF and ex situ generated chlorine gas within a two-chamber reactor setup. Notably, the process stands out for its simplicity by omitting the use of specialized equipment and generating less chemical waste than the previously reported works. While demonstrating high efficiency at room temperature, the novel approach provides access to a diverse array of products with moderate to excellent yields.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"275 ","pages":"Article 110276"},"PeriodicalIF":1.9,"publicationDate":"2024-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140308854","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 substituted (trifluoromethyl)alkenes: (Trifluoromethyl)alkylidenation of thioketones via CF3-thiiranes 取代的（三氟甲基）烯的合成：通过 CF3-环烷对硫酮进行（三氟甲基）亚烷基化反应
IF 1.9 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-03-23 DOI: 10.1016/j.jfluchem.2024.110273
Kohei Fuchibe , Tomoya Matsunobu , Junji Ichikawa
{"title":"Synthesis of substituted (trifluoromethyl)alkenes: (Trifluoromethyl)alkylidenation of thioketones via CF3-thiiranes","authors":"Kohei Fuchibe ,&nbsp;Tomoya Matsunobu ,&nbsp;Junji Ichikawa","doi":"10.1016/j.jfluchem.2024.110273","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2024.110273","url":null,"abstract":"<div><p>The synthesis of (trifluoromethyl)alkenes, including fully substituted variants, was achieved from thioketones with <em>in situ</em>-generated (trifluoromethyl)diazoalkanes [CF<sub>3</sub>C(R)=N<sub>2</sub>] (the Barton–Kellogg reaction). In the presence of sodium methoxide and a catalytic amount of tetrabutylammonium chloride, trifluoromethylated <em>N</em>-tosylhydrazones [CF<sub>3</sub>C(R)=NNHTs] derived from trifluoroacetaldehyde hemiacetal (R = H) or trifluoromethyl ketones (R = aryl or alkyl) were employed in the reactions with thioketones. The resulting (trifluoromethyl)diazoalkanes reacted with thioketones, forming (trifluoromethyl)thiirane intermediates. Treatment of these intermediates with trimethyl phosphite readily afforded the substituted (trifluoromethyl)alkenes. Theoretical calculations (DFT, B3LYP/6-31G*) showed that (trifluoromethyl)thiiranes, with less distortion than 2,2-difluorothiiranes, exhibited lower reactivity. Consequently, the involvement of a reducing agent was deemed necessary for the desulfurization step.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"275 ","pages":"Article 110273"},"PeriodicalIF":1.9,"publicationDate":"2024-03-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140190749","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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