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

Author(s)
Gribble, Michael William; Pirnot, Michael T; Bandar, Jeffrey; Liu, Richard; Buchwald, Stephen Leffler
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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.
Date issued
2017-01
URI
http://hdl.handle.net/1721.1/113039
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Gribble, Michael W., et al. “Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles.” Journal of the American Chemical Society, vol. 139, no. 6, Feb. 2017, pp. 2192–95. © 2017 American Chemical Society.
Version: Final published version
ISSN
0002-7863
1520-5126
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