Pub Date : 2026-04-01Epub Date: 2026-04-13DOI: 10.1016/j.jfluchem.2026.110568
Yang Li, Min Jiang, Jin-Tao Liu
A practical and efficient protocol for the α-perfluoroalkylthiolation of β-ketoesters was developed using perfluoroalkyl sulfoxides as perfluoroalkylthiolating reagents and trifluoromethanesulfonic anhydride (Tf₂O) as the activator. A series of α-perfluoroalkylthiolated ketone derivatives were synthesized in moderate to good yields under mild conditions. This transformation is compatible with both aromatic and aliphatic β-ketoesters and features a broad substrate scope. A possible reaction pathway was proposed based on experimental results.
{"title":"α-perfluoroalkylthiolation reaction of β-ketoesters with perfluoroalkyl sulfoxides","authors":"Yang Li, Min Jiang, Jin-Tao Liu","doi":"10.1016/j.jfluchem.2026.110568","DOIUrl":"10.1016/j.jfluchem.2026.110568","url":null,"abstract":"<div><div>A practical and efficient protocol for the α-perfluoroalkylthiolation of β-ketoesters was developed using perfluoroalkyl sulfoxides as perfluoroalkylthiolating reagents and trifluoromethanesulfonic anhydride (Tf₂O) as the activator. A series of α-perfluoroalkylthiolated ketone derivatives were synthesized in moderate to good yields under mild conditions. This transformation is compatible with both aromatic and aliphatic β-ketoesters and features a broad substrate scope. A possible reaction pathway was proposed based on experimental results.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"291 ","pages":"Article 110568"},"PeriodicalIF":1.9,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147703209","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}
Pub Date : 2026-04-01Epub Date: 2026-04-07DOI: 10.1016/j.jfluchem.2026.110566
Oleksii S. Timokhin , Andrii S. Rashevskyi , Olexandr V. Kucher , Dmytro Lesyk , Yuliia Holota , Petro Borysko , Stepan G. Pilyo , Oleksandr O. Grygorenko , Viktoriia S. Moskvina
Chroman-4-ols bearing 2-fluoroalkyl substituents are highly valuable 3D scaffolds in medicinal chemistry. Herein, we report a robust chemoenzymatic methodology for the asymmetric synthesis of enantioenriched 2-fluoroalkyl-substituted chroman-4-ols. The approach features a highly diastereoselective reduction of 2-fluoroalkyl chromones followed by an efficient pig liver esterase (PLE)-catalyzed hydrolytic kinetic resolution of the corresponding racemic acetates. This sequence provided access to both enantiomers of the target chroman-4-ols – directly via the enzymatically cleaved (2R,4R)-alcohols and through mild alcoholysis of the unreacted (2S,4S)-acetates – with excellent optical purities (up to >99% ee) and high selectivity factors (typically S > 100) for a series of derivatives bearing CHF2, CF3, C2F5, CF2Me, and CF2Cl groups. Furthermore, systematic physicochemical profiling uncovered a pronounced dichotomy in lipophilicity: while the reduction of non-fluorinated chromones to chromanols results in a negligible change or slight increase in LogP, the reduction of their fluorinated analogs causes a substantial drop in lipophilicity. The proposed chemotypes enable simultaneous control over both the 3D stereochemical space and the ADME profile, allowing for rational design of fluorinated chroman-based potential therapeutics.
{"title":"Expanding the biocatalytic toolbox: PLE-catalyzed kinetic resolution and lipophilicity modulation of 2-fluoroalkyl chroman-4-ols","authors":"Oleksii S. Timokhin , Andrii S. Rashevskyi , Olexandr V. Kucher , Dmytro Lesyk , Yuliia Holota , Petro Borysko , Stepan G. Pilyo , Oleksandr O. Grygorenko , Viktoriia S. Moskvina","doi":"10.1016/j.jfluchem.2026.110566","DOIUrl":"10.1016/j.jfluchem.2026.110566","url":null,"abstract":"<div><div>Chroman-4-ols bearing 2-fluoroalkyl substituents are highly valuable 3D scaffolds in medicinal chemistry. Herein, we report a robust chemoenzymatic methodology for the asymmetric synthesis of enantioenriched 2-fluoroalkyl-substituted chroman-4-ols. The approach features a highly diastereoselective reduction of 2-fluoroalkyl chromones followed by an efficient pig liver esterase (PLE)-catalyzed hydrolytic kinetic resolution of the corresponding racemic acetates. This sequence provided access to both enantiomers of the target chroman-4-ols – directly via the enzymatically cleaved (2<em>R</em>,4<em>R</em>)-alcohols and through mild alcoholysis of the unreacted (2<em>S</em>,4<em>S</em>)-acetates – with excellent optical purities (up to >99% <em>ee</em>) and high selectivity factors (typically <em>S</em> > 100) for a series of derivatives bearing CHF<sub>2</sub>, CF<sub>3</sub>, C<sub>2</sub>F<sub>5</sub>, CF<sub>2</sub>Me, and CF<sub>2</sub>Cl groups. Furthermore, systematic physicochemical profiling uncovered a pronounced dichotomy in lipophilicity: while the reduction of non-fluorinated chromones to chromanols results in a negligible change or slight increase in Log<em>P</em>, the reduction of their fluorinated analogs causes a substantial drop in lipophilicity. The proposed chemotypes enable simultaneous control over both the 3D stereochemical space and the ADME profile, allowing for rational design of fluorinated chroman-based potential therapeutics.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"291 ","pages":"Article 110566"},"PeriodicalIF":1.9,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147703212","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}
Pub Date : 2026-04-01DOI: 10.1016/j.jfluchem.2026.110565
Oleksandr S. Kanishchev , Andrew J.F. Edmunds , Peter Maienfisch , William R. Dolbier Jr
In this paper, we report synthesis and bioactivity studies of four 2-SF5-pyridyl substituted analogs of commercial neonicotinoid insecticides. Despite many known examples when substitution of CF3-group with SF5-group can enhance bioactivity profile of the target molecule, we have discovered that in the series of 2-SF5-pyridyl analogs of Sulfoxaflor, Flupyradifurone, Imidacloprid and Thiamethoxam that substitution did not lead to any improvement in biological activity as compared to trifluoromethyl- and/or chloro‑substituted congeners.
{"title":"Synthesis and biological activity of 2-SF5-pyridyl substituted analogs of commercial neonicotinoid insecticides Sulfoxaflor, Flupyradifurone, Imidacloprid and Thiamethoxam","authors":"Oleksandr S. Kanishchev , Andrew J.F. Edmunds , Peter Maienfisch , William R. Dolbier Jr","doi":"10.1016/j.jfluchem.2026.110565","DOIUrl":"10.1016/j.jfluchem.2026.110565","url":null,"abstract":"<div><div>In this paper, we report synthesis and bioactivity studies of four 2-SF<sub>5</sub>-pyridyl substituted analogs of commercial neonicotinoid insecticides. Despite many known examples when substitution of CF<sub>3</sub>-group with SF<sub>5</sub>-group can enhance bioactivity profile of the target molecule, we have discovered that in the series of 2-SF<sub>5</sub>-pyridyl analogs of Sulfoxaflor, Flupyradifurone, Imidacloprid and Thiamethoxam that substitution did not lead to any improvement in biological activity as compared to trifluoromethyl- and/or chloro‑substituted congeners.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"291 ","pages":"Article 110565"},"PeriodicalIF":1.9,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147656406","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}
Pub Date : 2026-04-01Epub Date: 2026-04-30DOI: 10.1016/j.jfluchem.2026.110571
Miguel Viar, Gabriel Zarca, Ane Urtiaga
Ionic liquids (ILs) are promising entrainers for the separation of azeotropic refrigerant mixtures, particularly within the ongoing transition toward low-global-warming-potential (GWP) alternatives. The development of extractive distillation processes requires reliable vapor–liquid equilibrium (VLE) data and accurate thermodynamic models. In this work, the solubility of several hydrofluorocarbons (R-32, R-125 and R-134a), hydrofluoroolefins (R-1234yf and R-1234ze(E)) and CO₂ in 1-ethyl-3-methylimidazolium bis(fluorosulfonyl)imide ([C₂C₁im][FSI]) was experimentally determined over temperatures from 283.15 to 323.15 K and pressures up to 1.1 MPa applying the isochoric saturation method. All refrigerant/IL systems were satisfactorily described using both the Peng–Robinson equation of state coupled with the Boston–Mathias mixing rule and the Non-Random Two-Liquid (NRTL) activity coefficient model, yielding average absolute deviations below 1% and 6%, respectively. The relative absorption performance was assessed through the Henry’s law constants and mixing thermodynamic properties, showing that the IL selected exhibited high ideal selectivity towards different refrigerant blends. In the case of R-410A, a near-azeotropic mixture of R-32 and R-125, the [C2C1im][FSI] selectivity was higher than previously reported for any other IL with a fluorinated anion, yet lower than for nitrile-based ILs. Furthermore, an upper-bound relationship between the ideal R-32/R-125 selectivity and R-32 absorption capacity was reported for the first time, establishing a quantitative benchmark for future IL screening and design. The presented data and its subsequent analysis expand the available thermodynamic knowledge for refrigerant/IL systems and provide a basis for future development an IL-based separation process for R-410A.
{"title":"Refrigerant solubility in 1-ethyl-3-methylimidazolium bis(fluorosulfonyl)imide and upper-bound for R-410A separation with ionic liquids","authors":"Miguel Viar, Gabriel Zarca, Ane Urtiaga","doi":"10.1016/j.jfluchem.2026.110571","DOIUrl":"10.1016/j.jfluchem.2026.110571","url":null,"abstract":"<div><div>Ionic liquids (ILs) are promising entrainers for the separation of azeotropic refrigerant mixtures, particularly within the ongoing transition toward low-global-warming-potential (GWP) alternatives. The development of extractive distillation processes requires reliable vapor–liquid equilibrium (VLE) data and accurate thermodynamic models. In this work, the solubility of several hydrofluorocarbons (R-32, R-125 and R-134a), hydrofluoroolefins (R-1234yf and R-1234ze(E)) and CO₂ in 1-ethyl-3-methylimidazolium bis(fluorosulfonyl)imide ([C₂C₁im][FSI]) was experimentally determined over temperatures from 283.15 to 323.15 K and pressures up to 1.1 MPa applying the isochoric saturation method. All refrigerant/IL systems were satisfactorily described using both the Peng–Robinson equation of state coupled with the Boston–Mathias mixing rule and the Non-Random Two-Liquid (NRTL) activity coefficient model, yielding average absolute deviations below 1% and 6%, respectively. The relative absorption performance was assessed through the Henry’s law constants and mixing thermodynamic properties, showing that the IL selected exhibited high ideal selectivity towards different refrigerant blends. In the case of R-410A, a near-azeotropic mixture of R-32 and R-125, the [C<sub>2</sub>C<sub>1</sub>im][FSI] selectivity was higher than previously reported for any other IL with a fluorinated anion, yet lower than for nitrile-based ILs. Furthermore, an upper-bound relationship between the ideal R-32/R-125 selectivity and R-32 absorption capacity was reported for the first time, establishing a quantitative benchmark for future IL screening and design. The presented data and its subsequent analysis expand the available thermodynamic knowledge for refrigerant/IL systems and provide a basis for future development an IL-based separation process for R-410A.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"291 ","pages":"Article 110571"},"PeriodicalIF":1.9,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147797782","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}
Pub Date : 2026-04-01Epub Date: 2026-03-19DOI: 10.1016/j.jfluchem.2026.110560
Duraisamy Udhayakumari , A. Nanthakumar
{"title":"Erratum to “Fluoride ion detection with heterocyclic chromogenic and fluorogenic probes: Molecular design and response pathways” [Journal of Fluorine Chemistry 290 (2026) 110543]","authors":"Duraisamy Udhayakumari , A. Nanthakumar","doi":"10.1016/j.jfluchem.2026.110560","DOIUrl":"10.1016/j.jfluchem.2026.110560","url":null,"abstract":"","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"291 ","pages":"Article 110560"},"PeriodicalIF":1.9,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147995617","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}
Pub Date : 2026-04-01DOI: 10.1016/j.jfluchem.2026.110563
Sakya S. Sen , Gašper Tavčar
{"title":"Obituary: Professor Herbert Walter Roesky (1935–2025) – transforming fluorine chemistry across the periodic table","authors":"Sakya S. Sen , Gašper Tavčar","doi":"10.1016/j.jfluchem.2026.110563","DOIUrl":"10.1016/j.jfluchem.2026.110563","url":null,"abstract":"","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"291 ","pages":"Article 110563"},"PeriodicalIF":1.9,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147995247","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}
Pub Date : 2026-04-01Epub Date: 2026-03-01DOI: 10.1016/j.jfluchem.2026.110551
Lana Hadi Chawishli , Aya Ibrahim , Svitlana Karamshuk , Hana Khan , Majid Motevalli , Saltanat Toiganbayeva , Isaac Abrahams , William P Gillin , Peter B Wyatt
{"title":"Corrigendum to “Luminescent, highly halogenated 2-(2-hydroxyphenyl)benzothiazole derivatives and their zinc complexes” [Journal of Fluorine Chemistry 2023, 270, 110165]","authors":"Lana Hadi Chawishli , Aya Ibrahim , Svitlana Karamshuk , Hana Khan , Majid Motevalli , Saltanat Toiganbayeva , Isaac Abrahams , William P Gillin , Peter B Wyatt","doi":"10.1016/j.jfluchem.2026.110551","DOIUrl":"10.1016/j.jfluchem.2026.110551","url":null,"abstract":"","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"291 ","pages":"Article 110551"},"PeriodicalIF":1.9,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147995619","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}
Pub Date : 2026-04-01Epub Date: 2026-04-22DOI: 10.1016/j.jfluchem.2026.110567
David Reiter, Selin Türk, Mario Schubert, Beate Koksch
Fluorine-labeling is a powerful technique in biomolecular NMR, yet its application is often hindered by a lack of standardized reference data for non-natural residues. In this work, we report the multinuclear random coil chemical shifts (1H, 13C, 15N, and 19F) for three commercially available, trifluoromethyl-bearing amino acids: trifluoroaminobutyric acid (TfAbu), trifluoronorvaline (TfNva), and 2-trifluoromethyltryptophan ((2-Tfm)Trp). These residues exhibit steric profiles comparable to the canonical amino acids Val, Leu, and Trp, respectively, making them suitable reporters for on-site 19F-labeling of proteins. Random coil data was recorded using a well-established hexapeptide model (Gly-Gly-X-Ala-Gly-Gly). The obtained chemical shifts are highly consistent with the dataset established by Wishart et al. (1995), thereby providing the foundational framework for NMR-based structure elucidation of complex, fluorine-labeled biomolecules.
{"title":"1H, 13C, 15N, and 19F random coil NMR shifts of trifluoromethyl-bearing amino acids","authors":"David Reiter, Selin Türk, Mario Schubert, Beate Koksch","doi":"10.1016/j.jfluchem.2026.110567","DOIUrl":"10.1016/j.jfluchem.2026.110567","url":null,"abstract":"<div><div>Fluorine-labeling is a powerful technique in biomolecular NMR, yet its application is often hindered by a lack of standardized reference data for non-natural residues. In this work, we report the multinuclear random coil chemical shifts (<sup>1</sup>H, <sup>13</sup>C, <sup>15</sup>N, and <sup>19</sup>F) for three commercially available, trifluoromethyl-bearing amino acids: trifluoroaminobutyric acid (TfAbu), trifluoronorvaline (TfNva), and 2-trifluoromethyltryptophan ((2-Tfm)Trp). These residues exhibit steric profiles comparable to the canonical amino acids Val, Leu, and Trp, respectively, making them suitable reporters for on-site <sup>19</sup>F-labeling of proteins. Random coil data was recorded using a well-established hexapeptide model (Gly-Gly-X-Ala-Gly-Gly). The obtained chemical shifts are highly consistent with the dataset established by Wishart et al. (1995), thereby providing the foundational framework for NMR-based structure elucidation of complex, fluorine-labeled biomolecules.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"291 ","pages":"Article 110567"},"PeriodicalIF":1.9,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147749733","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}
Pub Date : 2026-04-01Epub Date: 2026-04-15DOI: 10.1016/j.jfluchem.2026.110569
O. Hunsberger , G.S. Rakib , L. Vergari
Molten halide salts find use in a variety of applications, including fission reactors, fusion reactors, energy storage, and electrochemical processes. The breadth of applications of molten salts is made possible by the wide range of thermo-physical properties that can be obtained by tuning the salt composition. This wide range of variability can in part be attributed to acid-base equilibria, which can affect both solvent and solute behavior. While acid-base equilibria have been largely reviewed for chloride salts, owing to their wide use in electrochemical applications, only limited and sparse literature is present on acid-base equilibria in fluoride salts (i.e., fluoroacidity). Through this paper, we aim to clarify the inherent connection of fluoroacidity and molten salt chemical structure, illustrating how knowledge of the fluoroacidity of a given salt can be used to predict the physicochemical properties of such salt. In our analysis, we observe that fluoroacidity influences solvent (viscosity, self-diffusivities, electrical conductivity, thermal conductivity) and solute properties (solubility, diffusion coefficients, vapor pressures). We complement this analysis with a review of experimental and computational methods to evaluate the fluoroacidity of the salt, describing a wide range of techniques that can be used to indirectly probe fluoroacidity. The effects of radiation on fluoroacidity and the relationship between fluoroacidity and corrosion emerge as key knowledge gaps. Additionally, the development of direct methods for fluoroacidity quantification emerges as an important engineering objective.
{"title":"Acid-base equilibria in molten fluoride salts and their impact on molten salt reactors","authors":"O. Hunsberger , G.S. Rakib , L. Vergari","doi":"10.1016/j.jfluchem.2026.110569","DOIUrl":"10.1016/j.jfluchem.2026.110569","url":null,"abstract":"<div><div>Molten halide salts find use in a variety of applications, including fission reactors, fusion reactors, energy storage, and electrochemical processes. The breadth of applications of molten salts is made possible by the wide range of thermo-physical properties that can be obtained by tuning the salt composition. This wide range of variability can in part be attributed to acid-base equilibria, which can affect both solvent and solute behavior. While acid-base equilibria have been largely reviewed for chloride salts, owing to their wide use in electrochemical applications, only limited and sparse literature is present on acid-base equilibria in fluoride salts (i.e., fluoroacidity). Through this paper, we aim to clarify the inherent connection of fluoroacidity and molten salt chemical structure, illustrating how knowledge of the fluoroacidity of a given salt can be used to predict the physicochemical properties of such salt. In our analysis, we observe that fluoroacidity influences solvent (viscosity, self-diffusivities, electrical conductivity, thermal conductivity) and solute properties (solubility, diffusion coefficients, vapor pressures). We complement this analysis with a review of experimental and computational methods to evaluate the fluoroacidity of the salt, describing a wide range of techniques that can be used to indirectly probe fluoroacidity. The effects of radiation on fluoroacidity and the relationship between fluoroacidity and corrosion emerge as key knowledge gaps. Additionally, the development of direct methods for fluoroacidity quantification emerges as an important engineering objective.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"291 ","pages":"Article 110569"},"PeriodicalIF":1.9,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147749734","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}
Pub Date : 2026-04-01Epub Date: 2026-04-02DOI: 10.1016/j.jfluchem.2026.110564
Xiaolong Wang, Pei Zhang, Chunhua Han, Yang Zhang
Trifluoromethylthiolated indole and its derivatives are crucial in drug discovery and agrochemical development, yet their sustainable synthesis remains challenging. Herein, we reported an environmentally friendly and efficient electrophilic trifluoromethylthiolation strategy for the synthesis of CF3S‑substituted indoles and indolines in water. By using the low-toxicity and shelf-stable S-trifluoromethyl trifluoromethanesulfonothioate (TTST) as the CF3S precursor, a broad variety of C3- or C2-CF3S-substituted indoles and N1-CF3S-substituted indolines were obtained in good to excellent yields. This reaction exhibits simple operation, catalyst and additive-free condition, good functional group tolerance, and scale-up application.
{"title":"Catalyst and additive-free electrophilic trifluoromethylthiolation for the synthesis of CF3S-substituted indole and its derivatives in water","authors":"Xiaolong Wang, Pei Zhang, Chunhua Han, Yang Zhang","doi":"10.1016/j.jfluchem.2026.110564","DOIUrl":"10.1016/j.jfluchem.2026.110564","url":null,"abstract":"<div><div>Trifluoromethylthiolated indole and its derivatives are crucial in drug discovery and agrochemical development, yet their sustainable synthesis remains challenging. Herein, we reported an environmentally friendly and efficient electrophilic trifluoromethylthiolation strategy for the synthesis of CF<sub>3</sub>S‑substituted indoles and indolines in water. By using the low-toxicity and shelf-stable S-trifluoromethyl trifluoromethanesulfonothioate (TTST) as the CF<sub>3</sub>S precursor, a broad variety of C3- or C2-CF<sub>3</sub>S-substituted indoles and N1-CF<sub>3</sub>S-substituted indolines were obtained in good to excellent yields. This reaction exhibits simple operation, catalyst and additive-free condition, good functional group tolerance, and scale-up application.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"291 ","pages":"Article 110564"},"PeriodicalIF":1.9,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147600634","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}
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