The O-arylation methodology was subsequently employed to achieve more advanced ortho-functionalized azobenzene products that should be relevant in supramolecular chemistry, material science 18a, 43 and biological chemistry (Scheme 4). The reaction of bis(diaryl)iodonium salt 3g with phenol gave the ortho-diphenoxylated azobenzene 14 and the steroid estrone was arylated with reagent 3a to diaryl ether 15 in 60% yield. Moreover, the O-arylation of protected ribose 45 delivered the arylated derivative 16. Arylation of acetyl-protected cholic acid produced ester 17 in moderate yield, as the basic conditions caused partial hydrolysis of the acetate groups, with competing arylation to give byproduct 6 in 20% yield. Finally, the Oarylation of oleic acid produced the functionalized ester 18. It should be noted that 8-11 and 15-18 are novel orthoazobenzenes, illustrating the utility of the method to quickly reach a variety of targets. A comparison of our methodology with literature methods to reach the known products 4-7 and 12-14 is provided in the ESI.