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Article Abstract
A three-component strategy was developed to enable hydrodefluoroamination of β-trifluoromethyl enones by selectively activating two C(sp)-F bonds in the trifluoromethyl group. The method involved a sequence of carbonyl reduction, hydrodefluorination, and defluoroamination under transition-metal-free conditions. Synthetically useful ()-stereospecific α-fluoroenamides were obtained in good yields with diverse functional group tolerance, which could be easily transformed into valuable organofluorides and heterocycles. The carbonyl auxiliary exerts both electronic and steric impacts on the CF-alkenes, allowing for controllable and selective defluorination.
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| http://dx.doi.org/10.1021/acs.joc.4c01204 | DOI Listing |
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Transition-Metal-Free Hydrodefluoroamination of Trifluoromethyl Enones for the Synthesis of α-Fluoroenamides.
J Org Chem
July 2024
Technical Institute of Fluorochemistry, Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.
Article Synopsis
- A new strategy was created to transform β-trifluoromethyl enones through a three-step process: carbonyl reduction, hydrodefluorination, and defluoroamination, all without using transition metals.
- This approach successfully produced useful α-fluoroenamides in high yields, which can further be converted into important organofluorides and heterocycles.
- The carbonyl group aids in the reaction by affecting both the electronic and steric properties of the molecules, making the defluorination process more controllable and selective.