We report the silylation of primary C-H bonds located β to secondary and tertiary alcohols by exploiting perfluorinated esters as traceless directing groups. The conversion of a secondary or tertiary alcohol to a perfluoroalkyl ester and conversion of the ester to the corresponding silyl acetals by hydrosilylation allows for selective β-C(sp3)-H silylation catalyzed by the combination of [Ir(cod)OMe]2 and Me4Phen (3,4,7,8-tetramethyl-1,10-phenanthroline) to form 6-membered dioxasilinane. Tamao-Fleming oxidation of these dioxasilinane leads to 1,2 diols. The developed sequence was applied to a series of natural products containing hydroxyl groups.

中文翻译：

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通过全氟缩醛对醇的 β-C(sp3)-H 键进行无痕硅烷化

我们报告了通过利用全氟化酯作为无痕导向基团，将位于 β 的伯 CH 键硅烷化为仲醇和叔醇。仲醇或叔醇转化为全氟烷基酯以及酯通过氢化硅烷化转化为相应的甲硅烷基缩醛允许选择性 β-C(sp3)-H 硅烷化，由 [Ir(cod)OMe]2 和Me4Phen (3,4,7,8-tetramethyl-1,10-phenanthroline) 形成 6 元二氧杂硅烷。这些二恶硅烷的 Tamao-Fleming 氧化产生 1,2 二醇。开发的序列应用于一系列含有羟基的天然产物。