Cu-Catalyzed Oxidative Allylic C–H Arylation of Inexpensive Alkenes with (Hetero)Aryl Boronic Acids
Suman Kalyan Pal, Marine Cotard, Baptiste Gérardin, Christophe Hoarau, Cédric Schneider
Abstract
Herein, we present a regioselective Cu-catalyzed oxidative allylic C(sp3)–H arylation by radical relay using a broad range of heteroaryl boronic acids with inexpensive and readily available unactivated terminal and internal olefins. This C(sp2)–C(sp3) allyl coupling has the advantage of using cheap, abundant, and nontoxic Cu2O without the need to use prefunctionalized alkenes, thus offering an alternative method to allylic arylation reactions that employ more traditional coupling partners with preinstalled leaving groups (LGs) at the allylic position.
Topics & Concepts
Allylic rearrangementChemistryRegioselectivityArylCatalysisOxidative phosphorylationCombinatorial chemistryBoronic acidOxidative coupling of methaneOrganic chemistryMedicinal chemistryBiochemistryAlkylCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsCatalytic Cross-Coupling Reactions