Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles.
Title | Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles. |
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Authors | Gribble, M.W.; Pirnot, M.T.; Bandar, J.S.; Liu, R.Y.; Buchwald, S.L. |
Journal | J Am Chem Soc |
DOI | 10.1021/jacs.6b13029 |
Abstract |
We report a highly enantioselective CuH-catalyzed Markovnikov hydrosilylation of vinylarenes and vinyl heterocycles. This method has a broad scope and enables both the synthesis of isolable silanes and the conversion of crude products to chiral alcohols. Density functional theory calculations support a mechanism proceeding by hydrocupration followed by σ-bond metathesis with a hydrosilane. |