Synthesis of 2-(fluorinated aryl)pyridine derivatives via palladium-catalyzed C–H bond arylation of fluorobenzenes using 2-halopyridines as aryl sources

R. Boyaala (1, 2) , R. Touzani (1) , V. Guerchais (2) , Jean-François Soulé (2) , H. Doucet (2)

1 LCAE - Laboratoire de Chimie Appliquée et Environnement | Laboratory of Applied and Environmental Chemistry [Université Mohammed Premier Oujda]
2 ISCR - Institut des Sciences Chimiques de Rennes

We report herein on palladium-catalyzed direct arylation of (poly)fluorobenzene derivatives in the presence of 2-halopyridines for the one-step synthesis of 2-[(poly)fluorinated aryl]pyridine derivatives. The reactivity of 2-bromopyridines strongly dependents on its substituents at C6 position. The reaction proceeds nicely using a diphosphine palladium catalyst, and potassium pivalate/dimethylacetamide (PivOK/DMA) as catalytic system. The reaction was regioselective and occurred at the ortho-position of fluorine atoms.

Keywords: 2-Arylpyridine; Catalysis; Palladium; Fluorinated molecules; C–H activation

Domains: Chemical Sciences; Organic chemistry; Chemical Sciences; Catalysis

R. Boyaala, R. Touzani, V. Guerchais, Jean-François Soulé, H. Doucet. Synthesis of 2-(fluorinated aryl)pyridine derivatives via palladium-catalyzed C–H bond arylation of fluorobenzenes using 2-halopyridines as aryl sources. Tetrahedron Letters, 2017, 58 (33), pp.3205-3208. ⟨10.1016/j.tetlet.2017.06.075⟩. ⟨hal-01581219⟩