Palladium-catalyzed non-directed C–H bond arylation of difluorobenzenes and dichlorobenzenes bearing benzoxazole or benzothiazole

Fatma Abdellaoui (1, 2, 3) , Hamed Ben Ammar (1) , Jean-François Soulé (3) , Henri Doucet (3)

1 UM - Université de Monastir - University of Monastir
2 UTM - Université de Tunis El Manar
3 ISCR - Institut des Sciences Chimiques de Rennes

We report, herein, on palladium-catalyzed direct arylation of difluorobenzenes and dichlorobenzenes bearing benzoxazole or benzothiazole moieties, which don't act as directing groups. With moderate electron-withdrawing substituents on the aryl bromides as coupling partners, the reaction proceeds nicely using phosphine-free PdCl2 catalyst, and potassium pivalate/dimethylacetamide (PivOK/DMA) as catalytic system. The reaction was regioselective and occurred at the less hindered ortho-positions of fluorine or chlorine atoms

Mots clés: Arylation; C–H bond activation; Fluorine chemistry; Heterocycles; palladium

Domaines: Chimie

Fatma Abdellaoui, Hamed Ben Ammar, Jean-François Soulé, Henri Doucet. Palladium-catalyzed non-directed C–H bond arylation of difluorobenzenes and dichlorobenzenes bearing benzoxazole or benzothiazole. Catalysis Communications, 2015, 71, pp.13--16. ⟨10.1016/j.catcom.2015.07.025⟩. ⟨hal-01188221⟩