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Traceless Silylation of β-C(sp3)–H Bonds of Alcohols via Perfluorinated Acetals

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.

Authors:   Ala Bunescu; Trevor W. Butcher; John F. Hartwig
Journal:   Journal of the American Chemical Society
Year:   2018
DOI:   10.1021/jacs.7b12150
Publication date:   19-Jan-2018
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