Catalyst-free and visible light promoted trifluoromethylation and perfluoroalkylation of uracils and cytosines

Fluoroalkylated enaminones, such as trifluridine and 5-trifluoromethyluracil, have widespread applications in pharmaceuticals and agrochemicals. Although these kinds of pharmaceutical agent often bear CF3 and perfluoroalkyl motifs in the core structure, access to such analogues typically requires mu...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2018-12, Vol.54 (97), p.13662-13665
Hauptverfasser: Huang, Yang, Lei, Yun-Yun, Zhao, Liang, Gu, Jiwei, Yao, Qiuli, Wang, Ze, Li, Xiao-Fei, Zhang, Xingang, He, Chun-Yang
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Sprache:eng
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Zusammenfassung:Fluoroalkylated enaminones, such as trifluridine and 5-trifluoromethyluracil, have widespread applications in pharmaceuticals and agrochemicals. Although these kinds of pharmaceutical agent often bear CF3 and perfluoroalkyl motifs in the core structure, access to such analogues typically requires multi-step synthesis. Here, we report a mild, metal-free and operationally simple strategy for the direct perfluoroalkylation of uracils, cytosines and pyridinones through a visible-light induced pathway from perfluoroalkyl iodides. This photochemical transformation features synthetic simplicity, mild reaction conditions without any photoredox catalyst, and high functional group tolerance, providing a facile route for applications in medicinal chemistry.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc07759b