Related Experiment Video
Updated: Feb 12, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Palladium-Catalyzed Esterification of Carboxylic Acids with Aryl Iodides
Hiroyuki Kitano1, Hideto Ito2,3, Kenichiro Itami1,2,3
1Institute of Transformative Bio-Molecules (WPI-ITbM) , Nagoya University , Chikusa , Nagoya 464-8602 , Japan.
Abstract:
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.
Related Concept Videos
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
Acidity of Carboxylic Acids
Acid-Catalyzed Ring-Opening of Epoxides
Carboxylic Acids to Acid Chlorides

