Nickel-catalysed migratory hydroalkynylation and enantioselective hydroalkynylation of olefins with bromoalkynes

α-Chiral alkyne is a key structural element of many bioactive compounds, chemical probes, and functional materials, and is a valuable synthon in organic synthesis. Here we report a NiH-catalysed reductive migratory hydroalkynylation of olefins with bromoalkynes that delivers the corresponding benzyl...

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Autores principales: Jiang, Xiaoli, Han, Bo, Xue, Yuhang, Duan, Mei, Gui, Zhuofan, Wang, You, Zhu, Shaolin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8213830/
https://www.ncbi.nlm.nih.gov/pubmed/34145283
http://dx.doi.org/10.1038/s41467-021-24094-9
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author Jiang, Xiaoli
Han, Bo
Xue, Yuhang
Duan, Mei
Gui, Zhuofan
Wang, You
Zhu, Shaolin
author_facet Jiang, Xiaoli
Han, Bo
Xue, Yuhang
Duan, Mei
Gui, Zhuofan
Wang, You
Zhu, Shaolin
author_sort Jiang, Xiaoli
collection PubMed
description α-Chiral alkyne is a key structural element of many bioactive compounds, chemical probes, and functional materials, and is a valuable synthon in organic synthesis. Here we report a NiH-catalysed reductive migratory hydroalkynylation of olefins with bromoalkynes that delivers the corresponding benzylic alkynylation products in high yields with excellent regioselectivities. Catalytic enantioselective hydroalkynylation of styrenes has also been realized using a simple chiral PyrOx ligand. The obtained enantioenriched benzylic alkynes are versatile synthetic intermediates and can be readily transformed into synthetically useful chiral synthons.
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spelling pubmed-82138302021-07-01 Nickel-catalysed migratory hydroalkynylation and enantioselective hydroalkynylation of olefins with bromoalkynes Jiang, Xiaoli Han, Bo Xue, Yuhang Duan, Mei Gui, Zhuofan Wang, You Zhu, Shaolin Nat Commun Article α-Chiral alkyne is a key structural element of many bioactive compounds, chemical probes, and functional materials, and is a valuable synthon in organic synthesis. Here we report a NiH-catalysed reductive migratory hydroalkynylation of olefins with bromoalkynes that delivers the corresponding benzylic alkynylation products in high yields with excellent regioselectivities. Catalytic enantioselective hydroalkynylation of styrenes has also been realized using a simple chiral PyrOx ligand. The obtained enantioenriched benzylic alkynes are versatile synthetic intermediates and can be readily transformed into synthetically useful chiral synthons. Nature Publishing Group UK 2021-06-18 /pmc/articles/PMC8213830/ /pubmed/34145283 http://dx.doi.org/10.1038/s41467-021-24094-9 Text en © The Author(s) 2021 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Jiang, Xiaoli
Han, Bo
Xue, Yuhang
Duan, Mei
Gui, Zhuofan
Wang, You
Zhu, Shaolin
Nickel-catalysed migratory hydroalkynylation and enantioselective hydroalkynylation of olefins with bromoalkynes
title Nickel-catalysed migratory hydroalkynylation and enantioselective hydroalkynylation of olefins with bromoalkynes
title_full Nickel-catalysed migratory hydroalkynylation and enantioselective hydroalkynylation of olefins with bromoalkynes
title_fullStr Nickel-catalysed migratory hydroalkynylation and enantioselective hydroalkynylation of olefins with bromoalkynes
title_full_unstemmed Nickel-catalysed migratory hydroalkynylation and enantioselective hydroalkynylation of olefins with bromoalkynes
title_short Nickel-catalysed migratory hydroalkynylation and enantioselective hydroalkynylation of olefins with bromoalkynes
title_sort nickel-catalysed migratory hydroalkynylation and enantioselective hydroalkynylation of olefins with bromoalkynes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8213830/
https://www.ncbi.nlm.nih.gov/pubmed/34145283
http://dx.doi.org/10.1038/s41467-021-24094-9
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