Nickel-Catalyzed Carboalkenylation of 1,3-Dienes with Aldehydes and Alkenylzirconium Reagents: Access to Skipped Dienes
Cheng-Gang Wang, Yunxing Zhang, Simin Wang, Bin Chen, Yang Li, Hai‐Liang Ni, Yuanji Gao, Ping Hu, Bi‐Qin Wang, Peng Cao
Abstract
A regio- and stereoselective nickel-catalyzed three-component coupling reaction of aldehydes, 1,3-dienes, and alkenylzirconium reagents was realized. The ligand- and additive-free protocol afforded a convenient approach to the synthesis of skipped diene compounds bearing various functionals (e.g., hydroxyl, carbonyl, halide) and heterocyclic groups. The products were readily transformed into structurally diverse polyenes. The utility of this reaction was also demonstrated by the one-pot operation and scale-up preparation.
Topics & Concepts
ChemistryReagentCatalysisStereoselectivityDieneHalideNickelLigand (biochemistry)Combinatorial chemistryOrganic chemistryNatural rubberBiochemistryReceptorCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms