Synthesis of Heteroarylated Pyridines via a Double C-H Bond Functionalization using Palladium-catalyzed 1,4-Migration Combined with Direct Arylation - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue ChemCatChem Année : 2023

Synthesis of Heteroarylated Pyridines via a Double C-H Bond Functionalization using Palladium-catalyzed 1,4-Migration Combined with Direct Arylation

Résumé

The C-H bond functionalization of pyridyl C3-position of 4-arylpyridines using Pd 1,4-migration has been investigated. Under suitable reaction conditions, oxidative addition of 4-(2-bromoaryl)pyridines to palladium followed by a Pd 1,4-migration activates these pyridyl C3-positions. Next, the Pd-catalyzed coupling via C-H bond activation of the heteroarenes affords the C3-heteroarylated 4-arylpyridines. The new C-C bond created in this coupling reaction results from the functionalization of two C-H bonds. For this coupling reaction, a bromo-substituent on the aryl unit of 4-arylpyridines was employed as a traceless directing group. This heteroarylation method tolerates a range of substituents on the benzene ring as well as several heteroarenes. Moreover, from 3-arylpyridines, C2- or C4-functionalization of the pyridine ring also proved possible. In addition, this procedure uses an air-stable catalyst and an inexpensive base. Bromo-substituent as a traceless directing group was successfully employed to access heteroarylated pyridine derivatives via Pd 1,4-migration combined with direct heteroarylation. The new C-C bond created during this coupling reaction results from the functionalization of two C-H bonds.image

Domaines

Catalyse

Dates et versions

hal-04415205 , version 1 (24-01-2024)

Licence

Paternité

Identifiants

Citer

Mohamed Niyaz Vellala Syed Ali, Linhao Liu, Monika Ravi, Henri Doucet. Synthesis of Heteroarylated Pyridines via a Double C-H Bond Functionalization using Palladium-catalyzed 1,4-Migration Combined with Direct Arylation. ChemCatChem, 2023, Chemcatchem, pp.e202301226. ⟨10.1002/cctc.202301226⟩. ⟨hal-04415205⟩
12 Consultations
0 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More