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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...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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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. |
format | Online Article Text |
id | pubmed-9200125 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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