Chemoselective hydrosilylation of hydroxyketones
Marta L Lage1, Scott J Bader, Kanicha Sa-Ei
1Department of Chemistry, University of Michigan, Ann Arbor, MI 48109-1055, United States.
Abstract:
A chemoselective method for the hydrosilylation of ketones has been developed, using the combination of triphenylsilane and a catalyst prepared from Ni(COD)2 and the simple N-heterocyclic carbene IMes. The most notable feature of this method is that free hydroxyls are largely unaffected, thus providing a simple one-step procedure for the conversion of hydroxyketones to mono-protected diols, wherein the protecting group is exclusively installed on the ketone-derived hydroxyl. The process is typically high yielding with both simple ketones and more complex hydroxyketone substrates.
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