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

Rui Shang; Yao Fu; Jia-Bin Li; Song-Lin Zhang; Qing-Xiang Guo; Lei Liu

doi:10.1021/ja900984x

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

J Am Chem Soc. 2009 Apr 29;131(16):5738-9. doi: 10.1021/ja900984x.

Authors

Rui Shang¹, Yao Fu, Jia-Bin Li, Song-Lin Zhang, Qing-Xiang Guo, Lei Liu

Affiliation

¹ Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.

PMID: 19338301
DOI: 10.1021/ja900984x

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.