Synthesis of Aromatic Esters via Pd-Catalyzed Decarboxylative Coupling of Potassium Oxalate Monoesters with Aryl Bromides and Chlorides

Rui Shang(Tsinghua University), Yao Fu(University of Science and Technology of China), Jiabin Li(University of Science and Technology of China), Songlin Zhang(University of Science and Technology of China), Qing‐Xiang Guo(University of Science and Technology of China), Lei Liu(University of Science and Technology of China)
Journal of the American Chemical Society
April 1, 2009
Cited by 260

Abstract

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.


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