Synthesis of aromatic esters via Pd-catalyzed decarboxylative coupling of potassium oxalate monoesters with aryl bromides and chlorides.

Pd-catalyzed decarboxylative cross-coupling of aryl iodides, bromides, and chlorides with potassium oxalate monoesters has been discovered. This reaction is potentially useful for laboratory-scale synthesis of aryl and alkenyl esters. Bulky, electron-rich bidentate phosphine ligands are preferred in the reaction, whereas Cu is not needed for decarboxylation. Theoretical calculations suggest a five-coordinate Pd(II) transition state for decarboxylation with an energy barrier of approximately 30 kcal/mol.