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Electrophilic iodination of thiophene and its electron‐poor derivatives has been studied with KICl2 in dichloromethane and methanol using density function theory. KICl2 easily dissociates forming KCl and ICl, the latter being the iodinating agent. ICl forms an adduct with thiophene (π‐complex) followed by a nucleophilic attack of the ICl component by the aromatic component that forms the C–I bond...