A method for the direct C(sp2)-H trifluoromethylation of enamides, including biologically relevant isoindolinones, isoquinolinones and 2-pyridinones using TMSCF3 under oxidative conditions is presented. The protocol is convenient, operationally simple and exhibits high tolerance across a multitude of relevant handles and functional groups.
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http://dx.doi.org/10.1039/c8cc04907f | DOI Listing |
Org Process Res Dev
November 2024
Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium.
The development of sustainable trifluoromethylations of enamides is of great interest to the pharmaceutical industry. Herein, we demonstrate a sustainable direct electrochemical trifluoromethylation method in a microflow cell, using Langlois reagent, without the need for a supporting electrolyte, oxidants, or any additive under mild conditions. This method can be applied to various substrates with a yield of up to 84%.
View Article and Find Full Text PDFOrg Biomol Chem
October 2024
Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu, 214122, China.
Facilitated by an electron donor-acceptor (EDA) complex, an efficient β-trifluoromethylation and perfluoroalkylation of enamides with Togni reagent or perfluoroalkyl iodides is presented under transition-metal-free, photocatalyst-free and mild reaction conditions. Notably, using this photocatalyst-free strategy, direct trifluoromethylation and perfluoroalkylation of quinoxalin-2(1)-one derivatives was also achieved a photoactive electron donor-acceptor complex.
View Article and Find Full Text PDFChem Sci
July 2024
Graduate School of Engineering, Nagoya University B2-3(611), Furo-cho, Chikusa Nagoya 464-8603 Japan
Here, we report a highly effective dearomative (3 + 2) cycloaddition reaction between isoquinolinium ylides and α,β-enamides, α,β-γ,δ-dienamides, or an α,β-γ,δ-ε,ζ-trienamide, which is catalyzed by a chiral π-Cu(ii) complex (1-10 mol%) and proceeds in a site-selective, /-selective, and enantioselective manner. The (3 + 2) cycloaddition involving the α,β-enamides proceeds with high -selectivity and enantioselectivity. This method is applicable to various substrates including α-substituted, α,β-disubstituted, or β,β-disubstituted α,β-enamides, which are compounds with an intrinsically low reactivity.
View Article and Find Full Text PDFChemistryOpen
July 2023
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, P. R. China.
A novel Ru(phen) Cl -catalyzed free-radical chlorotrifluoromethylation reaction of unactivated olefins was investigated. Substituted 8-aminoquinoline-derived inert enamides were reacted with the Togni regent to afford a broad range of Cl-containing trifluoromethyl derivatives in good yields. The reaction proceeded at 90 °C and experimental result shows that the chlorine source of the products originated from LiCl.
View Article and Find Full Text PDFInt J Mol Sci
December 2022
Department of Analytical Chemistry, Faculty of Natural Sciences, Comenius University, Ilkovicova 6, 842 15 Bratislava, Slovakia.
A series of thirty-two anilides of 3-(trifluoromethyl)cinnamic acid (series ) and 4-(trifluoromethyl)cinnamic acid (series ) was prepared by microwave-assisted synthesis. All the compounds were tested against reference strains ATCC 29213 and ATCC 29212 and resistant clinical isolates of methicillin-resistant (MRSA) and vancomycin-resistant (VRE). All the compounds were evaluated in vitro against ATCC 700084 and CAMP 5644.
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