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Ruthenium-Catalyzed E-Selective Alkyne Semihydrogenation with Alcohols as Hydrogen Donors
[Image: see text] Selective direct ruthenium-catalyzed semihydrogenation of diaryl alkynes to the corresponding E-alkenes has been achieved using alcohols as the hydrogen source. The method employs a simple ruthenium catalyst, does not require external ligands, and affords the desired products in &g...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7343281/ https://www.ncbi.nlm.nih.gov/pubmed/32027128 http://dx.doi.org/10.1021/acs.joc.9b02721 |
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author | Ekebergh, Andreas Begon, Romain Kann, Nina |
author_facet | Ekebergh, Andreas Begon, Romain Kann, Nina |
author_sort | Ekebergh, Andreas |
collection | PubMed |
description | [Image: see text] Selective direct ruthenium-catalyzed semihydrogenation of diaryl alkynes to the corresponding E-alkenes has been achieved using alcohols as the hydrogen source. The method employs a simple ruthenium catalyst, does not require external ligands, and affords the desired products in > 99% NMR yield in most cases (up to 93% isolated yield). Best results were obtained using benzyl alcohol as the hydrogen donor, although biorenewable alcohols such as furfuryl alcohol could also be applied. In addition, tandem semihydrogenation–alkylation reactions were demonstrated, with potential applications in the synthesis of resveratrol derivatives. |
format | Online Article Text |
id | pubmed-7343281 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-73432812020-07-09 Ruthenium-Catalyzed E-Selective Alkyne Semihydrogenation with Alcohols as Hydrogen Donors Ekebergh, Andreas Begon, Romain Kann, Nina J Org Chem [Image: see text] Selective direct ruthenium-catalyzed semihydrogenation of diaryl alkynes to the corresponding E-alkenes has been achieved using alcohols as the hydrogen source. The method employs a simple ruthenium catalyst, does not require external ligands, and affords the desired products in > 99% NMR yield in most cases (up to 93% isolated yield). Best results were obtained using benzyl alcohol as the hydrogen donor, although biorenewable alcohols such as furfuryl alcohol could also be applied. In addition, tandem semihydrogenation–alkylation reactions were demonstrated, with potential applications in the synthesis of resveratrol derivatives. American Chemical Society 2020-02-06 2020-03-06 /pmc/articles/PMC7343281/ /pubmed/32027128 http://dx.doi.org/10.1021/acs.joc.9b02721 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. |
spellingShingle | Ekebergh, Andreas Begon, Romain Kann, Nina Ruthenium-Catalyzed E-Selective Alkyne Semihydrogenation with Alcohols as Hydrogen Donors |
title | Ruthenium-Catalyzed E-Selective
Alkyne Semihydrogenation with Alcohols as Hydrogen Donors |
title_full | Ruthenium-Catalyzed E-Selective
Alkyne Semihydrogenation with Alcohols as Hydrogen Donors |
title_fullStr | Ruthenium-Catalyzed E-Selective
Alkyne Semihydrogenation with Alcohols as Hydrogen Donors |
title_full_unstemmed | Ruthenium-Catalyzed E-Selective
Alkyne Semihydrogenation with Alcohols as Hydrogen Donors |
title_short | Ruthenium-Catalyzed E-Selective
Alkyne Semihydrogenation with Alcohols as Hydrogen Donors |
title_sort | ruthenium-catalyzed e-selective
alkyne semihydrogenation with alcohols as hydrogen donors |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7343281/ https://www.ncbi.nlm.nih.gov/pubmed/32027128 http://dx.doi.org/10.1021/acs.joc.9b02721 |
work_keys_str_mv | AT ekeberghandreas rutheniumcatalyzedeselectivealkynesemihydrogenationwithalcoholsashydrogendonors AT begonromain rutheniumcatalyzedeselectivealkynesemihydrogenationwithalcoholsashydrogendonors AT kannnina rutheniumcatalyzedeselectivealkynesemihydrogenationwithalcoholsashydrogendonors |