Gold Catalyzed Decarboxylative Cross-Coupling of Iodoarenes

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.