4.8 Article

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

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 131, 期 16, 页码 5738-+

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AMER CHEMICAL SOC
DOI: 10.1021/ja900984x

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资金

  1. 973 Program [2007CB210205]
  2. NNSFC [20602034, 20832004]
  3. NCET

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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 similar to 30 kcal/mol.

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