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Article Dans Une Revue Asian Journal of Organic Chemistry Année : 2023

Palladium‐catalyzed site‐selective C7 oxidative arylation of 4‐EWG‐1 H ‐Indazoles

Résumé

An efficient palladium‐catalyzed oxidative arylation of substituted 1$H$‐indazole with various arenes and heteroarenes as coupling partners is reported. A site selective C7 oxidative arylation was perfectly achieved with a directing electron‐withdrawing groups (EWG) located at the C4 position of the 1$H$‐indazole. The desired products are obtained in moderate to good yields from 4‐NO$_2$ or 4‐CO$_2$ Me 1$H$‐indazoles and various (hetero)aryls as coupling partners in the presence of Pd(OAc)$_2$ as catalyst, phenanthroline as ligand, Ag$_2$ CO$_3$ as oxidant and NaOH as the base. Density functional theory was also conducted for reaction mechanism comprehension. This approach provides a highly effective, direct, and atom economical way to build C7‐ (het)arylated 1$H$‐indazole compounds.

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Chimie
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Dates et versions

hal-04234929 , version 1 (10-10-2023)

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Chaimae Ouazzani Chahdi, Khalid Boujdi, Nabil El Brahmi, Monique Mathé-Allainmat, Hachim Mouhi Eddine, et al.. Palladium‐catalyzed site‐selective C7 oxidative arylation of 4‐EWG‐1 H ‐Indazoles. Asian Journal of Organic Chemistry, 2023, 12, pp.e2023002. ⟨10.1002/ajoc.202300285⟩. ⟨hal-04234929⟩
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