The introduction of trifluoromethyl group can significantly improve the functions of organic molecules, such as pharmaceuticals, agrochemicals and organic functional materials. The precedent trifluoromethylations for six-membered N-heteroaromatic compounds can be classified into radical trifluoromethylation and anionic trifluoromethylation. The former reaction (radical trifluoromethylation) proceeds under mild condition, but the regioselectivity is a problem due to the high reactivity of the CF3 radical. On the other hand, the latter reaction (anionic trifluoromethylation) has good regioselectivity, but highly activated substrate (N-OBF2CF3 or N-alkylated compound) should be use. An ideal method of introducing trifluoromethyl group is regioselective and direct C−H trifluoromethylation. Herein, we developed 2-position-selective and direct C−H trifluoromethylation of quinoline derivatives by combination of hydrogen fluoride and hypervalent silicon chemistry. The reaction proceeded at room temperature with high functional group tolerance. Furthermore, the reaction was applicable to late-stage trifluoromethylation for the bioactive compound, quinine having multiple functional groups. In this poster presentation, the optimization studies, scope and limitations will be discussed in detail.

2-Position-Selective C-H Trifluoromethylation of Quinoline Derivatives

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