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Palladium-Catalyzed Esterification of Carboxylic Acids with Aryl Iodides

  • Hiroyuki Kitano
    Hiroyuki Kitano
    Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya 464-8602, Japan
    More by Hiroyuki Kitano
  • , 
  • Hideto Ito*
    Hideto Ito
    Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
    JST-ERATO, Itami Molecular Nanocarbon Project, Nagoya University, Chikusa, Nagoya 464-8602, Japan
    *E-mail: [email protected] (H. Ito).
    More by Hideto Ito
    Orcidhttp://orcid.org/0000-0002-4034-6247
  • , and 
  • Kenichiro Itami*
    Kenichiro Itami
    Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya 464-8602, Japan
    Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
    JST-ERATO, Itami Molecular Nanocarbon Project, Nagoya University, Chikusa, Nagoya 464-8602, Japan
    *E-mail: [email protected] (K. Itami).
    More by Kenichiro Itami
    Orcidhttp://orcid.org/0000-0001-5227-7894
Cite this: Org. Lett. 2018, 20, 8, 2428–2432
Publication Date (Web):April 4, 2018
https://doi.org/10.1021/acs.orglett.8b00775
Copyright © 2018 American Chemical Society
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    Abstract

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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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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.8b00775.

    • Detailed experimental procedures and spectral data for all compounds, including scanned image of 1H, 13C NMR spectra (PDF)

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    Cited By

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    21. Fei Hou, Xi-Cun Wang, Zheng-Jun Quan. Efficient synthesis of esters through oxone-catalyzed dehydrogenation of carboxylic acids and alcohols. Organic & Biomolecular Chemistry 2018, 16 (48) , 9472-9476. https://doi.org/10.1039/C8OB02539H
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