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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Detalhes bibliográficos
Principais autores: Gribble, Michael William, Pirnot, Michael T, Bandar, Jeffrey, Liu, Richard, Buchwald, Stephen Leffler
Outros Autores: Massachusetts Institute of Technology. Department of Chemistry
Formato: Artigo
Publicado em: American Chemical Society (ACS) 2018
Acesso em linha:http://hdl.handle.net/1721.1/113039
https://orcid.org/0000-0003-2008-3264
https://orcid.org/0000-0002-7896-1683
https://orcid.org/0000-0001-5418-3082
https://orcid.org/0000-0003-3875-4775
Descrição
Resumo: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.