Several synthetic methods for the preparation of 3-trifluoromethyl pyridine derivatives have been reported (Scheme 1). The trifluoromethylation of aryl halide or boronic acid with stoichiometric or catalytic amounts of copper salts has been developed, and these methods were used to synthesize 3-trifluoromethyl pyridines (Scheme 1A). Grushin et al. reported a Sandmeyer-type reaction of aniline derivatives via diazonium salts (Scheme 1A). Because these reactions require functionalized substrates, the direct transformation of C(sp 2 )-H bonds is highly desirable. To the best of our knowledge, the sole example of such a reaction was reported by Yu et al. (Scheme 1B). They introduced a directing group at the 4-position of the pyridine, and C-H trifluoromethylation occurred at the ortho-position (formal 3-position) instead. The reaction afforded a mixture of mono-and di-trifluoromethylated products and the directing group limited the structure of the substrates. Herein, we report the first 3-position-selective trifluoromethylation of pyridine rings based on nucleophilic activation. To do so, we focused on hydrosilylation for the nucleophilic activation of the pyridine rings (Scheme 1C).