Cobalt-Catalyzed Migration Isomerization of Dienes
Jiajin Zhao, Guo-Xiong Xu, Xue Wang, Jiren Liu, Xiang Ren, Xin Hong, Zhan Lu
Abstract
A cobalt-catalyzed multipositional isomerization of conjugated dienes has been reported for the first time using an 8-oxazoline iminoquinoline ligand. This reaction is operationally simple and atom-economical using readily available starting materials with an E/Z mixture to access disubstituted 1,3-dienes with excellent yields and good E,E stereoselectivity. The mechanism via alkene insertion of cobalt hydride species and β-H elimination of a π-allyl cobalt intermediate is proposed on the basis of deuterium labeling and control experiments and density functional theory calculations.
Topics & Concepts
IsomerizationChemistryCobaltCatalysisAlkeneStereoselectivityHydrideOxazolineLigand (biochemistry)Combinatorial chemistryComputational chemistryHydrogenOrganic chemistryBiochemistryReceptorAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry MethodsCatalytic C–H Functionalization Methods