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Article Dans Une Revue Chemistry - A European Journal Année : 2019

Palladium‐Catalyzed C8‐Arylation of Naphthalenes through C−H Activation: A Combined Experimental and Computational Study

Julian Garrec
Marie Cordier
Gilles Frison
Sébastien Prevost
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Résumé

Herein, a direct C8‐arylation reaction of 1‐amidonaphthalenes is described. By using diaryliodonium salts as arylating agents, the palladium‐catalyzed C−H activation reaction showed perfect C8 regioselectivity and a wide functional group tolerance. In most cases, the desired polyaromatic compounds were isolated in good to excellent yields. To explain the observed regioselectivity, DFT calculations were performed and highlighted the crucial role of the amide directing group. Finally, the utility of this method is showcased by the synthesis of benzanthrone derivatives.
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hal-02322041 , version 1 (21-10-2019)

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Julian Garrec, Marie Cordier, Gilles Frison, Sébastien Prevost. Palladium‐Catalyzed C8‐Arylation of Naphthalenes through C−H Activation: A Combined Experimental and Computational Study. Chemistry - A European Journal, 2019, 25, pp.14441-14446. ⟨10.1002/chem.201903500⟩. ⟨hal-02322041⟩
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