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Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles
journal contribution
posted on 2017-01-24, 00:00 authored by Michael
W. Gribble, Michael T. Pirnot, Jeffrey S. Bandar, Richard Y. Liu, Stephen L. BuchwaldWe
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.
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Asymmetric Copper Hydride-Catalyzed Markovnikov HydrosilylationhydrocuprationDensityisolable silanesenantioselective CuH-catalyzed Markovnikov hydrosilylationVinylareneVinyl Heterocyclesscopechiral alcoholsvinylarenemethodsynthesiscrude productsconversionσ- bond metathesishydrosilanemechanism proceedingtheory calculations supportvinyl heterocycles
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