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

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 suppor...

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Detalles Bibliográficos
Publicado en:	Journal of the American Chemical Society Vol. 139; no. 6; pp. 2192 - 2196
Autores principales:	Gribble, Jr., Michael W., Pirnot, Michael T., Bandar, Jeffrey S., Liu, Richard Y., Buchwald, Stephen L.
Formato:	Artículo
Publicado:	American Chemical Society 2/15/2017
Materias:	Copper hydride Markovnikov's rule Hydrosilylation Aromatic compound derivatives Vinylation Asymmetric synthesis Enantioselective catalysis Density functional theory
Acceso en línea:	Ver este registro en EBSCOhost

Descripción
Sumario:	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.