Improving both the activity and selectivity of the C-H borylation reaction is currently a hot research topic but also a challenge. In this regard, we suggest a multistrategy combining directing group, coordination unsaturated metal center, and cationic character. Based on Reek's catalyst, we designed a new unsaturated cationic catalyst (1) featuring a directing group for C-H borylation. The calculated free energy barrier of C-H activation is only 7.2 kcal/mol, indicating that the cationic catalyst has higher activity than the original neutral catalyst in this process. Moreover, the comparison suggests that the ortho-C-H borylation pathway is more favorable than the meta and para pathways. The catalyst deconstructions are further performed and prove that the ortho-selectivity is attributed to hydrogen-bonding interactions between the directing group and the substrate, although the ortho site is sterically and electronically unfavorable.