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A synthetic approach to dibenzofurotropone derivatives <b>1</b> has been developed through the palladium-catalyzed cyclization of (2-bromoaryl)(3-arylfuran-2-yl)methanones <b>2</b> via the activation of arylic C–H bonds. Compounds <b>2</b> were easily prepared from the palladium-promoted acyl migration and cyclization of (<i>Z</i>)-pent-2-en-4-yn-1-yl acetates <b>3</b> in the presence of 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU), followed by oxidative decarbonylation and oxidation with O₂. Ten new tropone compounds are reported and these compounds show absorption in the UV-vis region and emission in the visible region.