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Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles
[Image: see text] 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 c...
| Autores principales: | , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical
Society
2017
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5386394/ https://www.ncbi.nlm.nih.gov/pubmed/28117996 http://dx.doi.org/10.1021/jacs.6b13029 |
| _version_ | 1782520762126565376 |
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| author | Gribble, Michael W. Pirnot, Michael T. Bandar, Jeffrey S. Liu, Richard Y. Buchwald, Stephen L. |
| author_facet | Gribble, Michael W. Pirnot, Michael T. Bandar, Jeffrey S. Liu, Richard Y. Buchwald, Stephen L. |
| author_sort | Gribble, Michael W. |
| collection | PubMed |
| description | [Image: see text] 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. |
| format | Online Article Text |
| id | pubmed-5386394 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2017 |
| publisher | American Chemical
Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-53863942017-04-11 Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles Gribble, Michael W. Pirnot, Michael T. Bandar, Jeffrey S. Liu, Richard Y. Buchwald, Stephen L. J Am Chem Soc [Image: see text] 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. American Chemical Society 2017-01-24 2017-02-15 /pmc/articles/PMC5386394/ /pubmed/28117996 http://dx.doi.org/10.1021/jacs.6b13029 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
| spellingShingle | Gribble, Michael W. Pirnot, Michael T. Bandar, Jeffrey S. Liu, Richard Y. Buchwald, Stephen L. Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles |
| title | Asymmetric
Copper Hydride-Catalyzed Markovnikov Hydrosilylation
of Vinylarenes and Vinyl Heterocycles |
| title_full | Asymmetric
Copper Hydride-Catalyzed Markovnikov Hydrosilylation
of Vinylarenes and Vinyl Heterocycles |
| title_fullStr | Asymmetric
Copper Hydride-Catalyzed Markovnikov Hydrosilylation
of Vinylarenes and Vinyl Heterocycles |
| title_full_unstemmed | Asymmetric
Copper Hydride-Catalyzed Markovnikov Hydrosilylation
of Vinylarenes and Vinyl Heterocycles |
| title_short | Asymmetric
Copper Hydride-Catalyzed Markovnikov Hydrosilylation
of Vinylarenes and Vinyl Heterocycles |
| title_sort | asymmetric
copper hydride-catalyzed markovnikov hydrosilylation
of vinylarenes and vinyl heterocycles |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5386394/ https://www.ncbi.nlm.nih.gov/pubmed/28117996 http://dx.doi.org/10.1021/jacs.6b13029 |
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