Hypervalent iodine (HVI) compounds represent a class of important and versatile reagents and reactants in organic synthesis. For example, iodine(V) species, such as 2-iodoxybenzoic acid (IBX), are recognized as effective oxidants for a wide range of synthetic transformations. More specifically, the double oxidation of phenols by IBX or related iodine(V) reagents delivers ortho-quinones in a highly regioselective manner. However, to date, a notable limitation of iodine(V)-mediated phenol oxidation chemistry is that these transformations are typically restricted to electron-rich phenol substrates.