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Cobalt-catalyzed branched selective hydroallylation of terminal alkynes
Here, we reported a cobalt-hydride-catalyzed Markovnikov-type hydroallylation of terminal alkynes with allylic electrophile to access valuable and branched skipped dienes (1,4-dienes) with good regioselectivity. This operationally simple protocol exhibits excellent functional group tolerance and exc...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Nature Publishing Group UK
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9349270/ https://www.ncbi.nlm.nih.gov/pubmed/35922446 http://dx.doi.org/10.1038/s41467-022-32291-3 |
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author | Chen, Jieping Ying, Jiale Lu, Zhan |
author_facet | Chen, Jieping Ying, Jiale Lu, Zhan |
author_sort | Chen, Jieping |
collection | PubMed |
description | Here, we reported a cobalt-hydride-catalyzed Markovnikov-type hydroallylation of terminal alkynes with allylic electrophile to access valuable and branched skipped dienes (1,4-dienes) with good regioselectivity. This operationally simple protocol exhibits excellent functional group tolerance and exceptional substrate scope. The reactions could be carried out in gram-scale with TON (turn over number) up to 1160, and the products could be easily derivatized. The preliminary mechanism of electrophilic allylation of α-selective cobalt alkenyl intermediate was proposed based on deuterium labeling experiment and kinetic studies. |
format | Online Article Text |
id | pubmed-9349270 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-93492702022-08-05 Cobalt-catalyzed branched selective hydroallylation of terminal alkynes Chen, Jieping Ying, Jiale Lu, Zhan Nat Commun Article Here, we reported a cobalt-hydride-catalyzed Markovnikov-type hydroallylation of terminal alkynes with allylic electrophile to access valuable and branched skipped dienes (1,4-dienes) with good regioselectivity. This operationally simple protocol exhibits excellent functional group tolerance and exceptional substrate scope. The reactions could be carried out in gram-scale with TON (turn over number) up to 1160, and the products could be easily derivatized. The preliminary mechanism of electrophilic allylation of α-selective cobalt alkenyl intermediate was proposed based on deuterium labeling experiment and kinetic studies. Nature Publishing Group UK 2022-08-03 /pmc/articles/PMC9349270/ /pubmed/35922446 http://dx.doi.org/10.1038/s41467-022-32291-3 Text en © The Author(s) 2022 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 Chen, Jieping Ying, Jiale Lu, Zhan Cobalt-catalyzed branched selective hydroallylation of terminal alkynes |
title | Cobalt-catalyzed branched selective hydroallylation of terminal alkynes |
title_full | Cobalt-catalyzed branched selective hydroallylation of terminal alkynes |
title_fullStr | Cobalt-catalyzed branched selective hydroallylation of terminal alkynes |
title_full_unstemmed | Cobalt-catalyzed branched selective hydroallylation of terminal alkynes |
title_short | Cobalt-catalyzed branched selective hydroallylation of terminal alkynes |
title_sort | cobalt-catalyzed branched selective hydroallylation of terminal alkynes |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9349270/ https://www.ncbi.nlm.nih.gov/pubmed/35922446 http://dx.doi.org/10.1038/s41467-022-32291-3 |
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