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Nickel-catalyzed cross-electrophile allylation of vinyl bromides and the modification of anti-tumour natural medicine β-elemene

Herein, we present a facile and efficient allylation method via Ni-catalyzed cross-electrophile coupling of readily available allylic acetates with a variety of substituted alkenyl bromides using zinc as the terminal reductant. This Ni-catalyzed modular approach displays excellent functional group t...

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Detalles Bibliográficos
Autores principales: Ye, Yang, Qi, Xiang, Xu, Bing, Lin, Ying, Xiang, Huan, Zou, Liang, Ye, Xiang-Yang, Xie, Tian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9200125/
https://www.ncbi.nlm.nih.gov/pubmed/35774167
http://dx.doi.org/10.1039/d2sc02054h
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author Ye, Yang
Qi, Xiang
Xu, Bing
Lin, Ying
Xiang, Huan
Zou, Liang
Ye, Xiang-Yang
Xie, Tian
author_facet Ye, Yang
Qi, Xiang
Xu, Bing
Lin, Ying
Xiang, Huan
Zou, Liang
Ye, Xiang-Yang
Xie, Tian
author_sort Ye, Yang
collection PubMed
description Herein, we present a facile and efficient allylation method via Ni-catalyzed cross-electrophile coupling of readily available allylic acetates with a variety of substituted alkenyl bromides using zinc as the terminal reductant. This Ni-catalyzed modular approach displays excellent functional group tolerance and a broad substrate scope, which the creation of a series of 1,4-dienes including several structurally complex natural products and pharmaceutical motifs. Moreover, the coupling strategy has the potential to realize enantiomeric control. The practicality of this transformation is demonstrated through the potent modification of the naturally antitumor active molecule β-elemene.
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spelling pubmed-92001252022-06-29 Nickel-catalyzed cross-electrophile allylation of vinyl bromides and the modification of anti-tumour natural medicine β-elemene Ye, Yang Qi, Xiang Xu, Bing Lin, Ying Xiang, Huan Zou, Liang Ye, Xiang-Yang Xie, Tian Chem Sci Chemistry Herein, we present a facile and efficient allylation method via Ni-catalyzed cross-electrophile coupling of readily available allylic acetates with a variety of substituted alkenyl bromides using zinc as the terminal reductant. This Ni-catalyzed modular approach displays excellent functional group tolerance and a broad substrate scope, which the creation of a series of 1,4-dienes including several structurally complex natural products and pharmaceutical motifs. Moreover, the coupling strategy has the potential to realize enantiomeric control. The practicality of this transformation is demonstrated through the potent modification of the naturally antitumor active molecule β-elemene. The Royal Society of Chemistry 2022-05-12 /pmc/articles/PMC9200125/ /pubmed/35774167 http://dx.doi.org/10.1039/d2sc02054h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Ye, Yang
Qi, Xiang
Xu, Bing
Lin, Ying
Xiang, Huan
Zou, Liang
Ye, Xiang-Yang
Xie, Tian
Nickel-catalyzed cross-electrophile allylation of vinyl bromides and the modification of anti-tumour natural medicine β-elemene
title Nickel-catalyzed cross-electrophile allylation of vinyl bromides and the modification of anti-tumour natural medicine β-elemene
title_full Nickel-catalyzed cross-electrophile allylation of vinyl bromides and the modification of anti-tumour natural medicine β-elemene
title_fullStr Nickel-catalyzed cross-electrophile allylation of vinyl bromides and the modification of anti-tumour natural medicine β-elemene
title_full_unstemmed Nickel-catalyzed cross-electrophile allylation of vinyl bromides and the modification of anti-tumour natural medicine β-elemene
title_short Nickel-catalyzed cross-electrophile allylation of vinyl bromides and the modification of anti-tumour natural medicine β-elemene
title_sort nickel-catalyzed cross-electrophile allylation of vinyl bromides and the modification of anti-tumour natural medicine β-elemene
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9200125/
https://www.ncbi.nlm.nih.gov/pubmed/35774167
http://dx.doi.org/10.1039/d2sc02054h
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