4.8 Article

Gold-Catalyzed Oxidative Acyloxylation of Arenes

Journal

ORGANIC LETTERS
Volume 13, Issue 22, Pages 6086-6089

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol202577c

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Funding

  1. Centre National de la Recherche Scientifique
  2. Ministere de l'Education et de la Recherche
  3. National Research Agency [ANR-09-JCJC-0078]
  4. Agence Nationale de la Recherche (ANR) [ANR-09-JCJC-0078] Funding Source: Agence Nationale de la Recherche (ANR)

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A variety of nonactivated hindered aromatic rings are acyloxylated (22 examples, up to 83% yield) in the presence of PPh3AuCl as the catalyst and di(acetoxy)iodobenzene as the oxidant. The reaction proceeds at 110 degrees C in an acid media and allows the formation of both hindered acetoxy and acyloxy derivatives. This methodology nicely complements the Pd-catalyzed arene acyloxylation reaction, which is not operating on hindered substrates and allows the Au-catalyzed unprecedented acyloxylation reaction of arenes, implying various carboxylic acids.

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