Nickel-catalyzed cross-electrophile allylation of vinyl bromides and the modification of anti-tumour natural medicine β-elemene
Yang Ye, Qi Xiang, Bing Xu, Ying‐Chih Lin, Huan Xiang, Liang Zou, Xiang‐Yang Ye, Tian Xie
Abstract
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.
Topics & Concepts
ElectrophileCatalysisAllylic rearrangementChemistryZincNickelCombinatorial chemistryOrganic chemistryCatalytic C–H Functionalization MethodsAsymmetric Synthesis and CatalysisCyclopropane Reaction Mechanisms