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Herein, an APEX reaction has been realized at the masked bay\u2010region for the efficient and rapid synthesis of valuable PAH, pyrene, bearing substitutions at the most challenging K\u2010region. Rh<jats:sup>III<\/jats:sup>\u2010catalyzed ketone\u2010directed C\u2212H activation at the <jats:italic>peri<\/jats:italic>\u2010position of a naphthyl\u2010derived ketone, alkyne\u2010insertion, intramolecular nucleophilic attack at the carbonyl\u2010group, dehydration, and aromatization steps occurred in one\u2010pot to effectuate the protocol. Employing this strategy, a two\u2010fold APEX reaction on enantiopure BINOL\u2010derived ketones provided access to axially\u2010chiral bipyrene derivatives. 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