reaction with isolation of an iodine(III) reagent 5, which is often a [hydroxy(tosyloxy)iodo]arene (L=OH, L'=OTs) or (diacetoxyiodo)arene (L=L'=OAc), prior to reaction with aryl reagent 6 (Route C). Since we developed the methodology in Routes A and B, the use of unsymmetrical diaryliodonium salts (Ar 1 ≠Ar 2 ) has considerably expanded, as they offer several advantages in their preparation and applications. When diaryliodonium salts are used in as arylating reagents, only one aryl group is generally transferred to the nucleophile. It is therefore desirable to install an inexpensive "dummy ligand" that forms the aryl iodide (ArI) by-product in the reaction. The chemoselectivity of the reaction, i.e. the selectivity in transferring the desired aryl group, relies on a balance of electronic and steric factors. Usually, high chemoselectivity is observed for transfer of the more electron-deficient aryl ligand under metal-free conditions. Selective transfer of an ortho-substituted aryl group, despite being more electron-rich, is favored with some nucleophiles. In the synthesis of unsymmetrical diaryliodonium salts with suitable electron-rich dummy groups, as well as when targeting products with two electrondeficient aryl groups, we have identified certain limitations with protocols A and B. Herein, we share our experience from many years of diaryliodonium salt synthesis and present updated protocols where we address how to efficiently access highly electron rich and electron poor diaryliodonium salts by tweaking the published conditions.