Thursday, June 26, 2008 - 2:30 PM
Federal Room A (Capital Hilton)
162

Decarboxylative Coupling of Aromatic Carboxylic Acids with Aryl Iodides and Unfuctionalized Arenes

Adelina M. Voutchkova, Abigail Coplin, and Robert Crabtree. Yale University, New Haven, CT

The use of carboxylic acids as partners in transition metal catalyzed biaryl coupling reactions is increasingly being explored, but the few reported reactions suffer from harsh reaction conditions and limited substrate scope. We report a microwave-assisted unsymmetric coupling in which readily available carboxylic acids are decarboxylated and coupled to either aryl halides or unfunctionalized arenes via C-H activation to give biaryl products in good to excellent yields. The catalyst system consists of a homogeneous palladium complex which catalyzes the cross coupling reaction, as well as a silver or copper salt which aids the decarboxylation of the aromatic carboxylate. Microwave heating enhances the yield, reduces the reaction time to 2-5 minutes and affords cleaner reactions than conventional methods.