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

Michael W GribbleMichael T PirnotJeffrey S BandarRichard Y LiuStephen L Buchwald

Published in: Journal of the American Chemical Society (2017)

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.

Keyphrases

density functional theory
room temperature
molecular dynamics
ionic liquid
solid state
oxide nanoparticles