Organic fluorine compounds have found widespread applications in pharmaceutical, agricultural, and materials science . The introduction of fluorine into organic molecules often strongly affects their properties, including their polarity, solubility, and lipophilicity. Among many organic fluorine-containing compounds, fluorinated arenes are used as semiconductors, light-emitting materials, and liquid crystals . Owing to its negative inductive effect, the incorporation of fluorine into materials leads to a decrease in orbital energy. As such, it is important to develop synthetic methods that provide access to aromatic molecules containing many C-F bonds , and the extreme targets of the research field are aromatic molecules wherein all hydrogen atoms are replaced with fluorine atoms, i.e., perfluoroarenes . However, methods to synthesize strained perfluoroarenes remain very limited. It is known that various fluorinated fullerenes (Fig. , top left) can be obtained from the addition of fluorine to the unsaturated bonds of fullerenes, but these are virtually the only examples of highly strained perfluoroarenes . Although Suzuki and co-workers have shown that perfluororubrene (Fig. , top right) possesses a twisted structure with a slight strain , a method to apply more strain to perfluoroarenes has not yet been reported.