Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Ekebergh, Andreas, Begon, Romain, Kann, Nina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
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
_version_ 1783555726664269824
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