The benzene ring is a prevalent core structure in both biologically significant compounds and functional materials. This prompts the development of innovative methods for synthesizing benzene derivatives. We present a divergent synthetic strategy for accessing 1,2-difuryl-substituted symmetrical benzene and highly functionalized fluorenones. In this approach, all aromatic cores are generated through a copper-mediated dimeric cycloaromatization cascade sequence, utilizing readily available dienynyl ketones. This protocol not only offers an alternative method for synthesizing symmetrical aromatics but also provides a framework for the oxidative transformation of furans into synthetically valuable substances.