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Journal of Fluorine Chemistry最新文献

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Predicting the increase in electron affinity of phenoxy upon fluorination 预测氟化时苯氧基电子亲和力的增加
IF 1.9 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-06-04 DOI: 10.1016/j.jfluchem.2024.110306
Connor J. Clarke , Jemma A. Gibbard , William D.G. Brittain , Jan R.R. Verlet
{"title":"Predicting the increase in electron affinity of phenoxy upon fluorination","authors":"Connor J. Clarke ,&nbsp;Jemma A. Gibbard ,&nbsp;William D.G. Brittain ,&nbsp;Jan R.R. Verlet","doi":"10.1016/j.jfluchem.2024.110306","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2024.110306","url":null,"abstract":"<div><p>The site-specific fluorination of organic compounds can alter their electron affinity, <em>EA</em>, which in turn can be used to control their reactivity, physical properties, or binding affinities. Using anion photoelectron spectroscopy, we show that for the multiply fluorinated phenoxy radical, the change in <em>EA</em> is predominantly additive per fluorination and can be predicted by the simple formula: Δ<em>EA</em> = <span><math><msub><mo>∑</mo><mi>i</mi></msub></math></span>Δ<em>EA<sub>i</sub></em> − Δ<em>EA</em><sub>C</sub>, where the numeric index <em>i</em> indicates the positions of fluorination. A small cooperative effect, Δ<em>EA</em><sub>C</sub>, destabilizes the anion, but this only accounts for 11 % of the total Δ<em>EA</em>, in the extreme case of pentafluorophenolate. Our experimental results are consistent with those calculated using density functional theory, demonstrating the suitability of electronic structure calculations in the prediction of fluorination effects, for practical use in the synthetic design of organofluorines.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"277 ","pages":"Article 110306"},"PeriodicalIF":1.9,"publicationDate":"2024-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0022113924000666/pdfft?md5=f172a7bc78139c8a25db0881ccb09f5b&pid=1-s2.0-S0022113924000666-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141250083","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
Chemically assisted degradation of 1,3-dioxo-2-difluoromethylene-4-trifluoromethoxy-5-difluoroammonium acetate dioxole 化学辅助降解 1,3-二氧代-2-二氟亚基-4-三氟甲氧基-5-二氟乙酸铵二恶英
IF 1.9 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-05-01 DOI: 10.1016/j.jfluchem.2024.110295
I. Wlassics, E. Lo Presti, R. Biancardi, C. Monzani, S. Barbieri
{"title":"Chemically assisted degradation of 1,3-dioxo-2-difluoromethylene-4-trifluoromethoxy-5-difluoroammonium acetate dioxole","authors":"I. Wlassics,&nbsp;E. Lo Presti,&nbsp;R. Biancardi,&nbsp;C. Monzani,&nbsp;S. Barbieri","doi":"10.1016/j.jfluchem.2024.110295","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2024.110295","url":null,"abstract":"<div><p>Recently, there has been a great strive to find new and efficient methods for the degradation of perfluorinated alkylated substances.</p><p>In this research work, we present recent advancements and results in the degradation of the surfactant “<em>c</em>C<sub>6</sub>O<sub>4</sub>-NH<sub>4</sub><sup>+</sup>” (<strong>I</strong>) (1,3-dioxo-2-difluoromethylene-4-trifluoromethoxy-5-difluoroammonium acetate dioxole) which demonstrates that it can be efficiently degraded in mild conditions, even at 20 °C.</p><p>The results of several different and innovative chemical strategies, such as DMSO induced decomposition at mild temperatures, thermal decomposition, acid/base chemistry induced decomposition, all of which decomposed <em>c</em>C<sub>6</sub>O<sub>4</sub> to CO<sub>2</sub> + HF/<em>F</em><sup><em>−</em></sup> in many cases ≥ 99.9%mol will be presented. All results will be supported by the respective kinetics, rates of reaction, thermodynamic reaction parameters, mechanisms of reaction, decomposition products, qualitative and quantitative spectroscopic analyses.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"276 ","pages":"Article 110295"},"PeriodicalIF":1.9,"publicationDate":"2024-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140947215","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
Bayesian optimization assisted screening conditions for visible light-induced hydroxy-perfluoroalkylation 贝叶斯优化法辅助筛选可见光诱导的羟基-全氟烷基化条件
IF 1.9 4区 化学
Journal of Fluorine Chemistry Pub Date : 2024-05-01 DOI: 10.1016/j.jfluchem.2024.110294
Koto Tagami , Masaru Kondo , Shinobu Takizawa , Nobuyuki Mase , Tomoko Yajima
{"title":"Bayesian optimization assisted screening conditions for visible light-induced hydroxy-perfluoroalkylation","authors":"Koto Tagami ,&nbsp;Masaru Kondo ,&nbsp;Shinobu Takizawa ,&nbsp;Nobuyuki Mase ,&nbsp;Tomoko Yajima","doi":"10.1016/j.jfluchem.2024.110294","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2024.110294","url":null,"abstract":"<div><p>The reaction conditions for the visible light-induced hydroxy-perfluoroalkylation of olefins were explored using Bayesian optimization (BO). This is the first application of BO to the photoreaction synthesis of fluorinated compounds. Five parameters, including light irradiation intensity, were simultaneously examined, thereby enabling the investigation of the reaction conditions using minimal experimentation. The key parameters were identified by calculating the correlation coefficients for each parameter. Furthermore, individual BO were achieved for different olefins and perfluoroalkyl bromides.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"276 ","pages":"Article 110294"},"PeriodicalIF":1.9,"publicationDate":"2024-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S002211392400054X/pdfft?md5=795873befd93170b3469e9426369fe27&pid=1-s2.0-S002211392400054X-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140823975","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
(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
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