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The preparation of decahydrocyclobuta[cd]indene skeleton was accomplished through rhodium(III)‐catalyzed hydroarylation and relay thiophene‐promoted intramolecular [2+2] cycloaddition. This tandem reaction exhibited broad substrate scope (24 examples) and good functional group compatibility. Control experiments revealed the important role of sulfur (S) heteroatom, thus a tentative mechanism with thiophene‐promoted double Michael additions was proposed to explain this formal [2+2] cycloaddition. Moreover, the resulting polycyclic products displayed potent anti‐cancer activities against breast cancer cell lines MDA‐MB‐468.