Electron withdrawing groups (EWG) such as NO2, CF3, OCF3, CN, and COMe were endurable to the reaction conditions, furnishing the desired products 3i-3m in good to excellent yields. Electrondonating substituents (EDG) like Ph, OMe, OPh, and NHAc were also tolerated (3n-3q). Even a free hydroxyl group could be carried through to product 3r, which is impressive as applications of hydroxy-substituted iodonium salts are scarce in literature. The reactivity was not influenced by ortho substitution in the iodonium salt, and target products 3t and 3u were secured in high yields. We were also delighted by the straightforward formation of sterically congested sulfides 3v and 3w, even allowing the synthesis of the triisopropylphenyl derivative 3x in high yield. The substitution pattern of the electron-deficient ring was investigated next, and the nitro group could be replaced by SO2CF3 to give sulfide 3y in excellent yield. While weaker EWG, such as CO2Me and CN, resulted in poor conversion, addition of further electron-withdrawing substituents was well tolerated (3z, 3aa). In the latter case, the CF3 group reinforced SNAr reactivity along with NO2 group. The introduction of additional fluoride substituents resulted in complete regioselectivity in favor of the desired transformation, with SNAr para to the nitro group yielding 3ab-3ad. Scheme 2. Diarylation scope. [a] Reaction conditions: 1 (0.2 mmol), 2d (0.28 mmol), DMF (0.2 M) under argon atmosphere for 18 h in absence of light, isolated yields are reported. [b] BF4 salt was used. [c] OTs salt was used. [d] Reaction performed at rt for 12 h and 60 °C for 6 h. [e] 1 synthesized using arylboronic acid.