Photolabile arylsilyl group: application to the oxidation of C-Si bonds

Article abstract of DOI:10.1016/j.tetlet.2007.10.057

(2,6-Dimethoxyphenyl)-dimethylsilyl group constitutes a new orthogonal masked hydroxyl group. Protodesilylation of this arylsilane occurs under photochemical conditions in the presence of alcohols such as hexafluoroisopropanol (HFIP) or isopropanol. These mild and neutral conditions thus allowed the oxidation of organosilicon compounds such as β-hydroxysilanes that are known to be prone to Peterson elimination.