An Ir(III)-catalyzed double C−H activation strategy has been developed for the synthesis of highly rigid spiro frameworks by means of ortho-functionalization of 2-aryl phthalazinediones and 2,3-diphenylcycloprop-2-en-1-ones using the Ir(III)/AgSbF 6 catalytic system. Similarly, 3-aryl-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxides undergo smooth cyclization with 2,3diphenylcycloprop-2-en-1-ones to afford a diverse range of spiro compounds in good yields with excellent selectivity. Additionally, 2arylindazoles provide the corresponding chalcone derivatives under similar reaction conditions.