4.8 Article

Palladium-Catalyzed Esterification of Carboxylic Acids with Aryl Iodides

Journal

ORGANIC LETTERS
Volume 20, Issue 8, Pages 2428-2432

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b00775

Keywords

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Funding

  1. ERATO program from JST [JPMJER1302]
  2. JSPS KAKENHI [JP26810057, JP16H00907, JP17K19155]
  3. SUMITOMO Foundation [141495]
  4. DAIKO Foundation
  5. World Premier International Research Center Initiative (WPI), Japan

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The first palladium-catalyzed esterification of carboxylic acids with aryl iodides is described. A palladium-based catalytic system consisting of IBnF (1,3-bis((pentafluorophenyl)methyl)imidazole-2-ylidene) ligand was found to significantly accelerate the aryl-O bond-forming esterification reaction. A series of aryl iodides and carboxylic acids undergoes a palladium-catalyzed coupling reaction to provide the corresponding aryl esters in moderate to good yields. In addition, sterically hindered aryl iodides and carboxylic acids were well-tolerated yielding the corresponding aryl esters.

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