Gold Catalyzed Decarboxylative Cross-Coupling of Iodoarenes
Ryan A. Daley, Aaron S. Morrenzin, Sharon R. Neufeldt, Joseph J. Topczewski
Abstract
This report details a decarboxylative cross-coupling of (hetero)aryl carboxylates with iodoarenes in the presence of a gold catalyst (>25 examples, up to 96% yield). This reaction is site specific, which overcomes prior limitations associated with gold catalyzed oxidative coupling reactions. The reactivity of the (hetero)aryl carboxylate correlates qualitatively to the field effect parameter (Fortho). Reactions with isolated gold complexes and DFT calculations support a mechanism proceeding through oxidative addition at a gold(I) cation with decarboxylation being viable at either a gold(I) or a silver(I) species.
Topics & Concepts
ChemistryDecarboxylationCatalysisReactivity (psychology)ArylYield (engineering)CarboxylateCoupling reactionOxidative additionPhotochemistryCombinatorial chemistryOrganic chemistryMedicineAlternative medicineMaterials scienceAlkylPathologyMetallurgyCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms