A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes

By exploiting the reactivity of a vinyl-Pd species, we control the regioselectivity in hydroallylation of alkynes under Pd-hydride catalysis. A monophosphine ligand and carboxylic acid combination promotes 1,5-dienes through a pathway involving isomerization of alkynes to allenes. In contrast, a bis...

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Detalles Bibliográficos
Autores principales: Ji, Ding-Wei, Hu, Yan-Cheng, Zheng, Hao, Zhao, Chao-Yang, Chen, Qing-An, Dong, Vy M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6598511/
https://www.ncbi.nlm.nih.gov/pubmed/31341584
http://dx.doi.org/10.1039/c9sc01527b
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author Ji, Ding-Wei
Hu, Yan-Cheng
Zheng, Hao
Zhao, Chao-Yang
Chen, Qing-An
Dong, Vy M.
author_facet Ji, Ding-Wei
Hu, Yan-Cheng
Zheng, Hao
Zhao, Chao-Yang
Chen, Qing-An
Dong, Vy M.
author_sort Ji, Ding-Wei
collection PubMed
description By exploiting the reactivity of a vinyl-Pd species, we control the regioselectivity in hydroallylation of alkynes under Pd-hydride catalysis. A monophosphine ligand and carboxylic acid combination promotes 1,5-dienes through a pathway involving isomerization of alkynes to allenes. In contrast, a bisphosphine ligand and copper cocatalyst favor 1,4-dienes via a mechanism that involves transmetalation. Our study highlights how to access different isomers by diverting a common organometallic intermediate.
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spelling pubmed-65985112019-07-24 A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes Ji, Ding-Wei Hu, Yan-Cheng Zheng, Hao Zhao, Chao-Yang Chen, Qing-An Dong, Vy M. Chem Sci Chemistry By exploiting the reactivity of a vinyl-Pd species, we control the regioselectivity in hydroallylation of alkynes under Pd-hydride catalysis. A monophosphine ligand and carboxylic acid combination promotes 1,5-dienes through a pathway involving isomerization of alkynes to allenes. In contrast, a bisphosphine ligand and copper cocatalyst favor 1,4-dienes via a mechanism that involves transmetalation. Our study highlights how to access different isomers by diverting a common organometallic intermediate. Royal Society of Chemistry 2019-05-16 /pmc/articles/PMC6598511/ /pubmed/31341584 http://dx.doi.org/10.1039/c9sc01527b Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Ji, Ding-Wei
Hu, Yan-Cheng
Zheng, Hao
Zhao, Chao-Yang
Chen, Qing-An
Dong, Vy M.
A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes
title A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes
title_full A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes
title_fullStr A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes
title_full_unstemmed A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes
title_short A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes
title_sort regioselectivity switch in pd-catalyzed hydroallylation of alkynes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6598511/
https://www.ncbi.nlm.nih.gov/pubmed/31341584
http://dx.doi.org/10.1039/c9sc01527b
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