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

ABSTRACT: 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.

SUBMITTER: Ye Y

PROVIDER: S-EPMC9200125 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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

Ye Yang Y Qi Xiang X Xu Bing B Lin Ying Y Xiang Huan H Zou Liang L Ye Xiang-Yang XY Xie Tian T

Chemical science 20220512 23

Herein, we present a facile and efficient allylation method <i>via</i> 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 stra ...[more]

PMID: 35774167

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