Roundabout mechanism

Wester term this process a roundabout mechanism, and they have some evidence for the occurrence of the double roundabout (two rotations of the methyl group about the iodine) as well ... 

Arylboronic esters (Figure 5.39) can be oxidized with H202 in acetic acid to give aryl borates, which can then be hydrolyzed to provide phenols. The mechanism for this oxidation is similar to that for the OOH- oxidation of trialkylboranes and is discussed in Section 11.4.3. In combination with the frequently simple synthesis of arylboronic esters one can thus achieve the overall conversions Ar—H — Ar—OH or Ar—Br —> Ar—OH in two or three steps. There is no metal-free alternative for these hydroxylations even if occasionally there are readily applicable roundabout routes, referred to in Figures 11.32 and 11.34. 

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