Despite the utility of ortho-substituted azobenzenes, there are few synthetic methods available for their synthesis (Scheme 1a). They can be prepared from appropriately substituted anilines 15a, 15c, 18 and further functionalized via nucleophilic substitution, or through transition metal-catalyzed C-H activation. In this fashion, azobenzenes decorated with carbon, and halide 19b, 20 substituents in the ortho-position have been synthesized. Drawbacks with these methods include the need for transition metal catalysts and long reaction times at elevated temperatures. Surprisingly, the literature is void of crosscoupling methods in the ortho-position, irrespective of whether the azobenzene moiety serves as organometallic nucleophilic component or as electrophilic halogenated cross-coupling partner, despite access to ortho-metalated azobenzenes. Hypervalent iodine(III) compounds are efficient reagents for a wide range of transformations under mild reaction conditions. Diaryliodonium salts have been recognized as highly reactive electrophilic arylating reagents with a variety of carbon and heteroatom nucleophiles under both metal-free and metal-catalyzed conditions. Furthermore, they are relatively non-toxic, bench-stable and easily synthesized through one-pot reactions of iodoarenes and arenes or arylboronic acids. We envisioned that the combination of azobenzene chemistry with iodine(III) chemistry could overcome the current limitations in synthesis of orthofunctionalized azobenzenes. Herein, we showcase the successful synthesis of ortho-azobenzene diaryliodonium salts and their application in metal-free arylation reactions to access hitherto unobtainable products (Scheme 1b).