This personal account summarizes our recent progress in the development of C-H transformations. We achieved ortho-selective C-H borylation and silylation using Lewis acid-base interaction between two substrates, and meta-selective C-H borylation using hydrogen bonding between a hydrogen donor unit of a ligand and a substrate functional group. Regioselective C-H trifluoromethylation and related reactions of 6-membered heteroaromatic compounds were realized at the 2-, 4-, and benzylic-positions of the heteroaromatic rings. In addition, we developed C-H transformations directed towards the synthesis of organic functional materials, such as highly soluble polyimides and π-conjugated molecules containing either heteroatom(s) or a Lewis acid-base interaction.