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Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles.

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.

SUBMITTER: Gribble MW

PROVIDER: S-EPMC5386394 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles.

Gribble Michael W MW Pirnot Michael T MT Bandar Jeffrey S JS Liu Richard Y RY Buchwald Stephen L SL

Journal of the American Chemical Society 20170201 6

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. ...[more]

PMID: 28117996

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