Mizoroki–Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C–C Bond Olefination
Meiling Wang, Hui Xu, Hanyuan Li, Biao Ma, Zhenyu Wang, Xing Wang, Hui‐Xiong Dai
Abstract
Mizoroki–Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C–C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C–H alkylation/ipso-Heck olefination.
Topics & Concepts
ChemistryArylKetoneHeck reactionAlkenePalladiumBond cleavageStyreneLigand (biochemistry)Organic chemistryCombinatorial chemistryMedicinal chemistryCatalysisAlkylPolymerReceptorBiochemistryCopolymerCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsOxidative Organic Chemistry Reactions