At Long Last: The Me3 Si Group as a Masked Alcohol.

For a long time, the Me3 Si group has been ostracized from the family of aryl- and heteroatom-substituted congeners for the difficulties associated with its further chemoselective manipulation into another synthetically useful functional group. A hypervalent iodine reagent has now been shown to do exactly that by electrophilic demethylation. Coupled with the Tamao-Fleming oxidation, the Me3 Si group becomes a placeholder for a hydroxy group.