To demonstrate the utility of the developed diarylation methodology, it was evaluated in the synthesis of more complex products using functionalized diaryliodonium salts. Applications of heteroaryl iodonium salts are still scarce in arylation methodologies, and a set of diverse heterocycle and complex scaffold-implanted iodonium salts were synthesized using literature methods. They were applied in the present reaction conditions and pyridine-derived sulfide 3ag and coumarin-derived product 3ah were obtained in very high yields (Scheme 2B). Next, we engaged a range of bioactive or drug molecules in novel latestage applications under transition metal-free conditions. The drugs were converted to the corresponding diaryliodonium salts, followed by reaction with 2d to provide the targeted Sfunctionalized products with complete regioselectivity. The phthalimide-derived sulfide 3ai was easily obtained, and the methyl ester derivative of gemfibrozil was converted to sulfide derivative 3aj in excellent yield. Likewise, the drugs clofibrate and isoxepac could be S-functionalized to give the desired products 3ak and 3al. A derivative of another NSAID drug, flurbiprofen, was applied to the salt synthesis and S-functionalization sequence to give the corresponding sulfide 3am.