A carbazole-incorporated N-confused porphyrin (NCP) 3 was synthesized via a Suzuki-Miyaura cross-coupling strategy and exhibits solvent-dependent 2H/3H tautomerism. Metalation studies revealed distinct metal-dependent reactivity: Ag+ afforded the planar Ag3+ complex 3-Ag, whereas Pd2+ selectively formed the cis-PdCl2-bridged dimer 4 through outer-nitrogen coordination. In contrast, Cu2+ induced diverse oxidative transformations. Initial formation of 3-Cu was followed by oxygen insertion and ring oxidation to generate unprecedented structures, including a Cu-C-C three-membered motif (6) and 4,5-dioxygenated 2-pyrrolidone units (7). Isotopic labeling experiments established CHCl3 as the carbon source of the formyl group. Spectroscopic analyses revealed pronounced structure-property correlations governed by the coordination geometry and π conjugation.