Palladium-catalyzed direct arylation of heteroarenes using 1-(bromophenyl)-1,2,3-triazoles as aryl source

Halima Hadj Mokhtar (1, 2) , Nouria Laidaoui (3, 2, 1) , Douniazad El Abed (1) , Jean-François Soulé (2) , Henri Doucet (2)

1 Université d'Oran 1 Ahmed Ben Bella [Oran]
2 ISCR - Institut des Sciences Chimiques de Rennes
3 USTO MB - Université des sciences et de la Technologie d'Oran Mohamed Boudiaf [Oran]

A variety of 1-aryl-1,2,3-triazoles contg. heteroarenes at C2-, C3- or C4-positions on the aryl ring I [Ar = 2-(2-ethyl-4-methyl-1,3-thiazol-5-yl)phenyl, 3-(5-methylthiophen-2-yl)phenyl, 4-(5-formyl-1-methylpyrrol-2-yl)phenyl, etc.; R = Me, Et, Ph] was successfully prepd. via palladium-catalyzed direct arylation. These couplings were performed by employing 1 mol% of phosphine-free Pd(OAc)2 catalyst with 1-(bromophenyl)-1,2,3-triazoles II (X = 2-Br, 3-Br, 4-Br) and heteroarenes such as 2-acetylthiophene, Me 2-methylfuran-3-carboxylate, 3,5-dimethylisoxazole, etc. as coupling partners. A wide variety of heteroarenes such as thiazoles, thiophenes, furans, pyrroles or isoxazoles was tolerated.

Mots clés: Triazoles; Heteroarenes; Palladium; C-H bond functionalization; Aryl bromides

Domaines: Chimie organique; Catalyse

Halima Hadj Mokhtar, Nouria Laidaoui, Douniazad El Abed, Jean-François Soulé, Henri Doucet. Palladium-catalyzed direct arylation of heteroarenes using 1-(bromophenyl)-1,2,3-triazoles as aryl source. Catalysis Communications, 2017, 92, pp.124-127. ⟨10.1016/j.catcom.2016.12.030⟩. ⟨hal-01475811⟩