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At Long Last: The Me3Si Group as a Masked Alcohol

Roy, Avijit; Oestreich, Martin

For a long time, the Me3Si 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 Me3Si group becomes a placeholder for a hydroxy group.
Published in: Angewandte Chemie, 10.1002/anie.202017157, Wiley