While MeCN resulted in no product formation, the reaction of 4aa in DCE at 50 °C gave the product 5aa in 23% yield (entry 1-2). By altering the amount of acid, a yield of up to 69% was achieved with 2.5 equivalents of TfOH (entry 3). Similar results were observed with DCM at 40 °C (entry 5). A higher amount of mCPBA did not lead to a better yield due to more washing required to remove the mCBA (entry 6). When we employed the chlorinated, electron-deficient iodoarene 4ah, the yield of 5ah dropped significantly (entry 7). Combining an electron-deficient heterocycle and an iodoarene with electron-withdrawing substituents results in a significantly decreased reactivity.