Cobalt-Catalyzed<i>Z</i>to<i>E</i>Isomerization of Alkenes: An Approach to (<i>E</i>)-β-Substituted Styrenes
Hongmei Liu, Man Xu, Cheng Cai, Jianhui Chen, Yugui Gu, Yuanzhi Xia
Abstract
An efficient cobalt-catalyzed Z to E isomerization of β-substituted styrenes using the amido-diphosphine ligand was developed, delivering the (E)-isomers with good functional tolerance and high stereoselectivity. The reaction could be scaled up to gram-scale with a catalyst loading of 0.1 mol %, using a mixture of (Z)- and (E)-alkene as the starting material. Preliminary mechanistic studies indicated that cobalt(I)-hydride and a benzylic-cobalt species were probably involved in the reaction, as supported by experiments and DFT calculations.
Topics & Concepts
IsomerizationCobaltChemistryCatalysisAlkeneHydrideStereoselectivityLigand (biochemistry)Medicinal chemistryOrganic chemistryHydrogenReceptorBiochemistryCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry MethodsChemical Synthesis and Analysis