| Autor: |
Bunescu A; Department of Chemistry, University of California , Berkeley, California 94720, United States., Butcher TW; Department of Chemistry, University of California , Berkeley, California 94720, United States., Hartwig JF; Department of Chemistry, University of California , Berkeley, California 94720, United States. |
| Abstrakt: |
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(sp 3 )-H silylation catalyzed by the combination of [Ir(cod)OMe] 2 and Me 4 Phen (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. |
