Transition metal-catalyzed aromatic functionalization reactions are highly important for the construction of various organic fine chemicals. In particular, the direct C(sp2)-H bond transformation of (hetero)aromatics is currently recognized to be highly useful in organic synthesis, as it can realize short-step sequences leading to target molecules. We have been studying aromatic cross-coupling reactions through C-H bond activation/cleavage leading to new C-C and C-heteroatom bonds. The research strategies involve directing group (DG) control and utilization of unique properties of reaction substrates and catalysts, which enable efficient regioselective direct coupling reactions. In this account, our recent work is briefly summarized, mainly focused on the synthetic methods of benzo-fused multi-ring heterocyclic compounds of potent interest in pharmaceutical and material chemistry.