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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...

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Detalles Bibliográficos
Autores principales: Chen, Jieping, Ying, Jiale, Lu, Zhan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2022
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.
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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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