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- Title
Palladium‐Catalyzed C8‐Arylation of Naphthalenes through C−H Activation: A Combined Experimental and Computational Study.
- Authors
Garrec, Julian; Cordier, Marie; Frison, Gilles; Prévost, Sébastien
- Abstract
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.
- Subjects
NAPHTHALENE; AMIDES; FUNCTIONAL groups; HOMOGENEOUS catalysis; ARYLATION; NAPHTHALENE derivatives
- Publication
Chemistry - A European Journal, 2019, Vol 25, Issue 63, p14441
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201903500