A novel palladium-catalyzed one-step dichalcogenation of cyclic diaryliodonium salts using readily available chalcogen sources (R-SH/-SeH) is described. This method enables the efficient synthesis of a diverse range of 2,2'-dichalcogenated biaryls under mild reaction conditions and achieves modest to good yields. Notably, this strategy displays both high regioselectivity and excellent functional group tolerance. Compared with previous approaches, this system offers superior performance, providing a versatile and practical route to valuable biaryl scaffolds.