Catalytic oxidative trifluoromethylation of imidazopyridines has been carried out at room temperature through the functionalization of the sp(2) C-H bond employing Langlois reagent under ambient air. A library of 3-(trifluoromethyl)imidazo[1,2-a]pyridines with broad functionalities have been synthesized regioselectively. This methodology is also applicable to imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole.
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http://dx.doi.org/10.1021/jo502928e | DOI Listing |
Environ Sci Technol
January 2025
Department of Chemistry, University of Alberta, Edmonton Alberta T6G 2G2, Canada.
Trifluoroacetic acid (TFA) is a ubiquitous environmental contaminant; however, its sources are poorly constrained. One understudied source is from the photochemical reactions of aromatic compounds containing -CF moieties (aryl-CF) including many pharmaceuticals and agrochemicals. Here, we studied the aqueous photochemistry of 4-(trifluoromethyl)phenol (4-TFMP), a known transformation product of the pharmaceutical fluoxetine.
View Article and Find Full Text PDFNat Commun
January 2025
State Key Laboratory of Petroleum Molecular & Process Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, China.
Intensified host-guest electronic interplay within stable metal-organic cages (MOCs) presents great opportunities for applications in stimuli response and photocatalysis. Zr-MOCs represent a type of robust discrete hosts for such a design, but their host-guest chemistry in solution is hampered by the limited solubility. Here, by using pyridinium-derived cationic ligands with tetrakis(3,5-bis(trifluoromethyl)phenyl)borate (BAr) as solubilizing counteranions, we report the preparation of soluble Zr-MOCs of different shapes (1-4) that are otherwise inaccessible through a conventional method.
View Article and Find Full Text PDFAnal Chem
December 2024
Shandong Provincial Key Laboratory of Detection Technology for Tumor Markers, College of Chemistry and Chemical Engineering, Linyi University, Linyi 276000, China.
To answer the call for effective and timely intervention in cardiovascular diseases (CVDs), the development of fluorescent probes that can precisely identify atherosclerotic plaques, the root cause of various fatal CVDs, is highly desirable but remains a great challenge. Herein, by integrating bis(trifluoromethyl)benzyl and phenothiazine into the coumarin matrix, a robust fluorescent probe, NOR1, has been developed. NOR1 responds sequentially to lipid droplets (LDs) and HClO via fluorescence turn-on and ratiometric readouts, respectively, with a fast response rate (within 70 s for LDs and 80 s for HClO), excellent sensitivity (detection limit: 0.
View Article and Find Full Text PDFOrg Lett
January 2025
Technical Institute of Fluorochemistry, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.
A three-component reaction of trifluoromethyl enones, phosphine oxides, and alcohols in water solution is developed. This defluorinative reaction occurs through a cascade process involving defluorophosphorylation, defluoroalkyloxylation, and defluoroheteroannulation, enabling the modular synthesis of furans with four distinct substituents: 2-alkyloxy, 3-trifluoromethyl, 4-phosphoryl, and 5-(hetero)aryl groups. Moreover, apart from alcohol substrates, the scope of nucleophiles could be further extended to phenols, azacycles, or sulfonamide.
View Article and Find Full Text PDFEur J Med Chem
February 2025
Ph.D. Program in Drug Discovery and Development Industry, College of Pharmacy, Taipei Medical University, Taipei, Taiwan; School of Pharmacy, Taipei Medical University, Taipei, Taiwan. Electronic address:
Protein disulfide isomerase (PDI) regulates multiple protein functions by catalyzing the oxidation, reduction, and isomerization of disulfide bonds. The enzyme is considered a potential target for treating thrombosis. We previously developed a potent PDI inhibitor, CPD, which contains the propiolamide as a warhead targeting cysteine residue in PDI.
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