Direct Coupling of Polyfluoroarenes with Acylsilanes Under Metal-Free Conditions

The installation of polyfluoroaryl group in functional molecules is of interest due to the presence of polyfluoroarenes in pharmaceuticals, agrochemicals, and advanced materials. Herein, we report the direct coupling of polyfluoroarenes with acylsilanes for synthesis of fluorinated benzylic alcohols in the presence of a catalytic base. This reaction could tolerate a wide range of polyfluoroarenes and polyfluoroheteroarenes, providing an efficient entry to fluoroarylated compounds. Deuteration experiments showed that the hydrogen source in the product was mainly from the polyfluoroarenes. The utility of this method was demonstrated by the derivatization of the product and the synthesis of a fluorinated analogue with antituberculous activity.