Iridium-Catalyzed Regioselective Silylation of Secondary Alkyl C–H Bonds for the Synthesis of 1, 3-Diols

B Li, M Driess, JF Hartwig

Index: Li, Bijie; Driess, Matthias; Hartwig, John F. Journal of the American Chemical Society, 2014 , vol. 136, # 18 p. 6586 - 6589

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Citation Number: 31

Abstract

We report Ir-catalyzed intramolecular silylation of secondary alkyl C–H bonds.(Hydrido) silyl ethers, generated in situ by dehydrogenative coupling of a tertiary or conformationally restricted secondary alcohol with diethylsilane, undergo regioselective silylation at a secondary C–H bond γ to the hydroxyl group. Oxidation of the resulting oxasilolanes in the same vessel generates 1, 3-diols. This method provides a strategy to synthesize 1, 3-diols ...