Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles

Classical 1,4-dicarbofunctionalization of 1,3-enynes employs organometallic reagents as nucleophiles to initiate the reaction. We report a copper-catalyzed 1,4-alkylarylation of 1,3-enynes with alkyl diacyl peroxides as masked alkyl electrophiles and aryl boronic acids as nucleophiles, selectively a...

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Detalles Bibliográficos
Autores principales: Ye, Changqing, Li, Yajun, Zhu, Xiaotao, Hu, Shengmin, Yuan, Daqiang, Bao, Hongli
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/PMC6432612/
https://www.ncbi.nlm.nih.gov/pubmed/30996957
http://dx.doi.org/10.1039/c8sc05689g
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author Ye, Changqing
Li, Yajun
Zhu, Xiaotao
Hu, Shengmin
Yuan, Daqiang
Bao, Hongli
author_facet Ye, Changqing
Li, Yajun
Zhu, Xiaotao
Hu, Shengmin
Yuan, Daqiang
Bao, Hongli
author_sort Ye, Changqing
collection PubMed
description Classical 1,4-dicarbofunctionalization of 1,3-enynes employs organometallic reagents as nucleophiles to initiate the reaction. We report a copper-catalyzed 1,4-alkylarylation of 1,3-enynes with alkyl diacyl peroxides as masked alkyl electrophiles and aryl boronic acids as nucleophiles, selectively affording structurally diversified tetrasubstituted allenes under mild conditions. Mechanistic studies suggest that an allenyl radical might be involved.
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spelling pubmed-64326122019-04-17 Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles Ye, Changqing Li, Yajun Zhu, Xiaotao Hu, Shengmin Yuan, Daqiang Bao, Hongli Chem Sci Chemistry Classical 1,4-dicarbofunctionalization of 1,3-enynes employs organometallic reagents as nucleophiles to initiate the reaction. We report a copper-catalyzed 1,4-alkylarylation of 1,3-enynes with alkyl diacyl peroxides as masked alkyl electrophiles and aryl boronic acids as nucleophiles, selectively affording structurally diversified tetrasubstituted allenes under mild conditions. Mechanistic studies suggest that an allenyl radical might be involved. Royal Society of Chemistry 2019-02-19 /pmc/articles/PMC6432612/ /pubmed/30996957 http://dx.doi.org/10.1039/c8sc05689g Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Ye, Changqing
Li, Yajun
Zhu, Xiaotao
Hu, Shengmin
Yuan, Daqiang
Bao, Hongli
Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles
title Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles
title_full Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles
title_fullStr Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles
title_full_unstemmed Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles
title_short Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles
title_sort copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6432612/
https://www.ncbi.nlm.nih.gov/pubmed/30996957
http://dx.doi.org/10.1039/c8sc05689g
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