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Metal-Free Synthesis of 2-Fluoroalkylated Quinolines Using Polyfluoroalkanoic Acids as Direct Fluorine Sources
- Nan, Jiang, Hu, Yan, Chen, Pu, Ma, Yangmin
- Organic letters 2019 v.21 no.7 pp. 1984-1988
- carboxylic acids, chemical reactions, fluorine, moieties, perfluorocarbons, quinolines
- A novel [5 + 1] cyclization of 2-vinylanilines with polyfluoroalkanoic acids under catalyst- and additive-free conditions was successfully implemented. The approach directly employs very low-cost and readily available polyfluoroalkanoic acids as both C1 synthons and fluoroalkyl building blocks. This method provides concise access to diverse 2-fluoroalkylated (CF₃, C₂F₅, C₃F₇, CF₂H, CF₂Cl, and CF₂Br) quinolines in good yields with excellent functional group tolerance in high yield on a gram scale.