Ligand-Controlled C-O Bond Coupling of Carboxylic Acids and Aryl Iodides: Experimental and Computational Insights

Palladium-catalyzed cross-coupling reactions between carboxylic acids and aryl halides have several possible competitive pathways. Decarboxylative C-C bond coupling and C-H arylation are well established in the literature. However, direct C-O bond coupling between carboxylic acids and aryl halides has received little success. In this report, we describe a protocol for exclusive C-O bond formation, enabled by a bidentate N,N-ligand such as 1,10-phenanthroline. The reaction is general for a broad range of carboxylic acids and iodoarenes. Experimental evidence and computational results suggest a high energy barrier for the alternative pathway of decarboxylative carbon-carbon bond coupling.