Nickel-Catalyzed <i>Ipso/Ortho</i> Difunctionalization of Aryl Bromides with Alkynes and Alkyl Bromides via a Vinyl-to-Aryl 1,4-Hydride Shift
Yuli He, Marino Börjesson, Huayue Song, Yuhang Xue, Daning Zeng, Rubén Martı́n, Shaolin Zhu
Abstract
Polysubstituted arenes are ubiquitous structures in a myriad of medicinal agents and complex molecules. Herein, we report a new catalytic blueprint that merges the modularity of nickel catalysis for bond formation with the ability to enable a rather elusive 1,4-hydride shift at arene sp2 C–H sites, thus allowing access to ipso/ortho-difunctionalized arenes from readily available aryl halides under mild conditions and exquisite selectivity profile.
Topics & Concepts
ChemistryArylCatalysisHydrideNickelAlkylHalideCombinatorial chemistrySelectivityReductive eliminationMedicinal chemistryOrganic chemistryMetalCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsChemical Reactions and Isotopes