Aryl fluorides are important structural motifs in many pharmaceuticals. Although the Balz-Schiemann reaction provides an entry to aryl fluorides from aryldiazonium tetrafluoroborates, it suffers from drawbacks such as long reaction time, high temperature, toxic solvent, toxic gas release, and low functional group tolerance. Here, we describe a general method for the synthesis of aryl fluorides from aryldiazonium tetrafluoroborates using a piezoelectric material as redox catalyst under ball milling conditions in the presence of Selectfluor. This approach effectively addresses the aforementioned limitations. Furthermore, the piezoelectric material can be recycled multiple times. Mechanistic investigations indicate that this fluorination reaction may proceed via a radical pathway, and Selectfluor plays a dual role as both a source of fluorine and a terminal reductant.
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http://dx.doi.org/10.1002/anie.202307054 | DOI Listing |
Molecules
December 2024
Institute of Organic and Analytical Chemistry (ICOA UMR 7311), CNRS, University of Orleans, F-45067 Orléans, France.
The emergence of RNA viruses driven by global population growth and international trade highlights the urgent need for effective antiviral agents that can inhibit viral replication. Nucleoside analogs, which mimic natural nucleotides, have shown promise in targeting RNA-dependent RNA polymerases (RdRps). Starting from protected 5-iodouridine, we report the synthesis of -substituted-(1,3-diyne)-uridines nucleosides and their phosphoramidate prodrugs.
View Article and Find Full Text PDFChem Sci
November 2024
Molecular Inorganic Chemistry and Catalysis, Inorganic and Structural Chemistry, Center for Molecular Materials, Faculty of Chemistry, Universität Bielefeld Universitätsstrasse 25 D-33615 Bielefeld Germany http://www.ghadwalgroup.de.
The first carbocyclic gallylene [(ADC)Ga(GaI)] and bis-gallylene [(ADC)Ga] (ADC = PhC{N(Dipp)C}; Dipp = 2,6-iPrCH) featuring a central CGa ring annulated between two 1,3-imidazole rings are prepared by KC reductions of [(ADC)GaI]. Treatment of [(ADC)Ga] with Fe(CO) affords complex [(ADC)GaFe(CO)] in which each Ga(i) atom serves as a two-electron donor. [(ADC)Ga] activates white phosphorus (P) and the C -F bond of aryl fluorides (ArF) to yield compounds [(ADC)Ga(P)] and -/-[(ADC)GaF(Ar)], respectively.
View Article and Find Full Text PDFInt J Biol Macromol
January 2025
Faculty of Chemistry, Northeast Normal University, 5268 Renmin Street, Changchun 130024, PR China; College of Chemical Engineering, Changchun University of Technology, 2055 Yanan Street, Changchun 130024, PR China. Electronic address:
Solid polymer batteries (SPEs) are highly desirable for energy storage because of the urgent need for higher energy density and safer lithium ion batteries (LIBs). In this work, the single-ion lithium salt PAEK-LiCPSI was synthesized by grafting 3-chloropropanesulfonyl trifluoromethanesulimide lithium (LiCPSI) onto poly(aryl ether ketone) (PAEK). Nanocellulose (NCC), PAEK-LiCPSI, and poly(vinylidene fluoride) (PVDF-HFP) were compounded to obtain NCC reinforced high-performance nanofiber composite polymer electrolytes (NCC/PAEK/PVDF) through electrospinning, which presented tensile strength of 15.
View Article and Find Full Text PDFPharmaceuticals (Basel)
December 2024
N. P. Bechtereva Institute of the Human Brain, Russian Academy of Sciences, 197022 St. Petersburg, Russia.
-succinimidyl-[F]fluorobenzoate ([F]SFB) is commonly prepared through a three-step procedure starting from [F]fluoride ion. A number of methods for the single-step radiosynthesis of [F]SFB have been introduced recently, including the radiofluorination of diaryliodonium salts and the Cu-mediated F-fluorination of pinacol aryl boronates and aryl tributyl stannanes, but they still have the drawbacks of lengthy product purification procedures. In the present work, two approaches for the direct labeling of [F]SFB from diaryliodonium (DAI) salt () and pinacol aryl boronate () are evaluated, with a major focus on developing a fast and simple SPE-based purification procedure.
View Article and Find Full Text PDFOrg Biomol Chem
December 2024
School of Chemistry and Chemical Engineering/State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, Shihezi University, Shihezi 832003, P. R. China.
An organocatalytic method for the SuFEx click reaction of gaseous SOF is described. Different organic bases such as DBU, TBD, triethylamine and Hünig's base can efficiently catalyze the SuFEx of SOF with various phenols to produce aryl fluorosulfates in 61-97% yields. Under the same conditions, pyridone, pyrazolone and amines can also react with SOF to afford the corresponding heteroaryl fluorosulfates or sulfamoyl fluorides in good yields.
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