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Molecules containing trifluoromethoxyaryl groups are of interest in pharmaceutical, agrochemical, and materials science research, due to their unique physical and electronic properties. Many of the known methods to synthesize aryl trifluoromethyl ethers require harsh reagents and highly controlled reaction conditions and rarely occur when heteroaromatic units are present. The two-step -trifluoromethylation of phenols via aryl xanthates is one such method that suffers from these drawbacks. Herein, we report a method for the synthesis of aryl trifluoromethyl ethers from phenols by the facile conversion of the phenol to the corresponding aryl and heteroaryl xanthates with newly synthesized imidazolium methylthiocarbonothioyl salts and conversion of these xanthates to the trifluoromethyl ethers under mild reaction conditions.
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http://dx.doi.org/10.1021/acs.joc.9b02717 | DOI Listing |
Chem Sci
December 2024
MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University Hangzhou 310027 China
Cationic polymerization of vinyl ethers to access poly(vinyl ether) polymeric materials has been challenging due to stringent polymerization conditions and inevitable chain transfer. Herein we introduce a protocol using trifluoromethyl sulfonates to catalyze the polymerization of a series of vinyl ethers. These trifluoromethyl sulfonates are fully commercially available and can be stored under ambient conditions.
View Article and Find Full Text PDFBioorg Chem
December 2024
State Key Laboratory of Fine Chemicals, Department of Pharmaceutical Engineering, School of Chemical Engineering, Dalian University of Technology, 2 Linggong Road, Dalian 116024, PR China. Electronic address:
In this report, we disclose the design and synthesis of a series of 2-trifluoromethyl-2H- chromene ethers as novel COX-2 inhibitors with low ulcerogenicity. Among them, 6-fluoro-3-(4-methoxyphenyl)-2-(2-(thiophen-3-yl)ethoxy)-2-(trifluoromethyl)-2H-chromene (E25) significantly suppressed LPS-induced release of NO and PGE, expression of COX-2 and iNOS, and activation of NF-κB pathway. The inhibitory effect of E25 on human recombinant COX-2 (IC = 70.
View Article and Find Full Text PDFJ Org Chem
December 2024
Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205, P. R. China.
We report, for the first time, a visible-light-promoted Markovnikov hydroalkoxylation of α-trifluoromethyl alkenes with 1,2-diketones. This transformation proceeded smoothly in the presence of a tertiary amine (EtN), providing a series of enol ethers containing the trifluoromethylated tetrasubstituted center in moderate to excellent yields. In this protocol, hydrogen atom transfer between this amine and 1,2-diketone substrate affords a ketyl radical and an α-aminoalkyl radical, which engages in the formation of a radical anion of the α-CF alkene via a single electron transfer.
View Article and Find Full Text PDFJ Inorg Biochem
January 2025
Department of Organic Chemistry, University of Zagreb, Faculty of Chemical Engineering and Technology, Marulićev trg 19, 10000 Zagreb, Croatia. Electronic address:
Novel 6-substituted 2-(trifluoromethyl)quinoline 5a-5e and coumarin 6a-6d ligands with aldoxime ether linked pyridine moiety were synthesized by O-alkylation of quinoline and coumarin with (E)-picolinaldehyde oxime and subsequently with [Re(CO)Cl] gave rhenium(I) tricarbonyl complexes 5a-5e and 6a-6d that were fully characterized by NMR, single-crystal X-ray diffraction, IR and UV-Vis spectroscopy. The results of antiproliferative evaluation of quinoline and coumarin ligands and their rhenium(I) tricarbonyl complexes on various human tumor cell lines, including acute lymphoblastic leukemia (CCRF-CEM), acute monocytic leukemia (THP1), cervical adenocarcinoma (HeLa), colon adenocarcinoma (CaCo-2), T-cell lymphoma (HuT78), and non-tumor human fibroblasts (BJ) showed that the quinoline complexes 5a-5e had higher inhibitory activity than coumarin complexes 6a-6d, particularly against T-cell lymphoma (HuT78) cells. 6-Methoxy-2-(trifluoromethyl)quinoline 5e and 6-methylcoumarin 6d, and their rhenium(I) tricarbonyl complexes 5e and 6d were found to arrest the cell cycle of HuT78 cells by causing a significant accumulation of cells in the G0/G1 phase and a marked decrease in the number of cells in the G2/M phase.
View Article and Find Full Text PDFTurk J Chem
October 2024
Department of Chemistry, Gebze Technical University, Gebze, Kocaeli, Turkiye.
Cryogels containing isocyanate reactive groups were synthesized via photopolymerization of 2-isocyanoethyl methacrylate (ICEMA) and poly(ethylene glycol) methyl ether methacrylate (PEGMEMA). By changing the PEGMEMA and ICEMA ratios, cryogel series with varying ratios of reactive isocyanate groups were successfully prepared. The cryogels were characterized using Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis, scanning electron microscope, and rheometry.
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