Aryl Acid-Alcohol Cross-Coupling: C(sp)-C(sp) Bond Formation from Nontraditional Precursors.

Alcohols and aryl carboxylic acids are among the most commercially abundant, synthetically versatile, and operationally convenient building blocks in organic chemistry. Despite their widespread availability, the direct formation of C(sp)-C(sp) bonds from these functional groups remains a challenge. Recently, our group developed robust protocols to harness alcohols as alkyl radical precursors, but the activation of aryl acids remains relatively unexplored. Herein, we describe the merger of N-heterocyclic carbene (NHC)-mediated deoxygenation and nickel-mediated decarbonylation of aryl acids toward C(sp)-C(sp) bond formation. The utility of this method is demonstrated through the synthesis of a diverse range of aryl-alkyl cross-coupled products and the late-stage functionalization of complex molecules, including drugs, natural products, and biomolecules.