<i>N</i>-Heterocyclic Carbene–Nickel-Catalyzed Regioselective Diarylation of Aliphatic-1,3-Dienes
Hongyu Wang, Chen‐Fei Liu, Tong‐De Tan, Kyna Ru Bin Khoo, Ming Joo Koh
Abstract
Aliphatic-1,3-dienes represent a problematic class of substrates for catalytic 1,2-dicarbofunctionalization due to inherent complications of undesired allylic rearrangement, consequently giving rise to inseparable isomeric product mixtures. Here, we show that aliphatic-1,3-dienes can participate in highly efficient and site-selective 1,2-diarylation, by merging with an aryl triflate and arylmetal reagent in the presence of a sizeable N-heterocyclic carbene (NHC)–Ni(0) catalyst. Adducts containing tertiary or quaternary centers and those derived from multifunctional bioactive molecules could be obtained.
Topics & Concepts
CarbeneCatalysisRegioselectivityChemistryAllylic rearrangementReagentArylAdductTrifluoromethanesulfonateOrganic chemistryNickelMedicinal chemistryCombinatorial chemistryAlkylCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsN-Heterocyclic Carbenes in Organic and Inorganic Chemistry