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A Simple Nickel Catalyst Enabling an E‐Selective Alkyne Semihydrogenation

Stereoselective alkyne semihydrogenations are attractive approaches to alkenes, which are key building blocks for synthesis. With regards to the most atom‐economic reducing agent dihydrogen (H(2)), only few catalysts for the challenging E‐selective alkyne semihydrogenation have been disclosed, each...

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Autores principales: Thiel, Niklas O., Kaewmee, Benyapa, Tran Ngoc, Trung, Teichert, Johannes F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7027572/
https://www.ncbi.nlm.nih.gov/pubmed/31691388
http://dx.doi.org/10.1002/chem.201903850
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author Thiel, Niklas O.
Kaewmee, Benyapa
Tran Ngoc, Trung
Teichert, Johannes F.
author_facet Thiel, Niklas O.
Kaewmee, Benyapa
Tran Ngoc, Trung
Teichert, Johannes F.
author_sort Thiel, Niklas O.
collection PubMed
description Stereoselective alkyne semihydrogenations are attractive approaches to alkenes, which are key building blocks for synthesis. With regards to the most atom‐economic reducing agent dihydrogen (H(2)), only few catalysts for the challenging E‐selective alkyne semihydrogenation have been disclosed, each with a unique substrate scope profile. Here, we show that a commercially available nickel catalyst facilitates the E‐selective alkyne semihydrogenation of a wide variety of substituted internal alkynes. This results in a simple and broadly applicable overall protocol to stereoselectively access E‐alkenes employing H(2), which could serve as a general method for synthesis.
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spelling pubmed-70275722020-02-24 A Simple Nickel Catalyst Enabling an E‐Selective Alkyne Semihydrogenation Thiel, Niklas O. Kaewmee, Benyapa Tran Ngoc, Trung Teichert, Johannes F. Chemistry Full Papers Stereoselective alkyne semihydrogenations are attractive approaches to alkenes, which are key building blocks for synthesis. With regards to the most atom‐economic reducing agent dihydrogen (H(2)), only few catalysts for the challenging E‐selective alkyne semihydrogenation have been disclosed, each with a unique substrate scope profile. Here, we show that a commercially available nickel catalyst facilitates the E‐selective alkyne semihydrogenation of a wide variety of substituted internal alkynes. This results in a simple and broadly applicable overall protocol to stereoselectively access E‐alkenes employing H(2), which could serve as a general method for synthesis. John Wiley and Sons Inc. 2020-01-21 2020-02-03 /pmc/articles/PMC7027572/ /pubmed/31691388 http://dx.doi.org/10.1002/chem.201903850 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Full Papers
Thiel, Niklas O.
Kaewmee, Benyapa
Tran Ngoc, Trung
Teichert, Johannes F.
A Simple Nickel Catalyst Enabling an E‐Selective Alkyne Semihydrogenation
title A Simple Nickel Catalyst Enabling an E‐Selective Alkyne Semihydrogenation
title_full A Simple Nickel Catalyst Enabling an E‐Selective Alkyne Semihydrogenation
title_fullStr A Simple Nickel Catalyst Enabling an E‐Selective Alkyne Semihydrogenation
title_full_unstemmed A Simple Nickel Catalyst Enabling an E‐Selective Alkyne Semihydrogenation
title_short A Simple Nickel Catalyst Enabling an E‐Selective Alkyne Semihydrogenation
title_sort simple nickel catalyst enabling an e‐selective alkyne semihydrogenation
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7027572/
https://www.ncbi.nlm.nih.gov/pubmed/31691388
http://dx.doi.org/10.1002/chem.201903850
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