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At Long Last: The Me 3 Si Group as a Masked Alcohol
Author(s) -
Roy Avijit,
Oestreich Martin
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202017157
Subject(s) - hypervalent molecule , electrophile , aryl , group (periodic table) , reagent , alcohol , demethylation , functional group , chemistry , nucleophile , heteroatom , combinatorial chemistry , organic chemistry , alkyl , biochemistry , catalysis , gene expression , polymer , dna methylation , gene
For a long time, the Me 3 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 Me 3 Si group becomes a placeholder for a hydroxy group.
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