Palladium-Catalyzed Regioselective Direct Arylation of Benzofurazans at the C-4 Position

Imane Idris (1, 2) , Fazia Derridj (1) , Jean-François Soulé (2) , Henri Doucet (2)

1 LPCM - Laboratoire de physique et de chimie des matériaux [Tizi-Ouzou]
2 ISCR - Institut des Sciences Chimiques de Rennes

The palladium-catalyzed direct arylation of benzofurazans with aryl bromides to access 4-ary-lbenzofurazans proceeds in moderate-to-high yields using phosphine-free palladium acetate as the catalyst and potassium acetate as an inexpensive base. A wide variety of (hetero) aryl bromides, including bromopyridine and bromothiophene derivatives has been successfully employed. Palladium-catalyzed one-pot C-4, C-7-diarylation of benzofurazan was also achieved using a larger amount of aryl bromide. Moreover, the derivatization of 4-arylbenzofurazans into 4-arylquinaxolines is also reported.

Keywords: palladium; quinaxolines; benzofurazans; catalysis; c-h activation

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

Imane Idris, Fazia Derridj, Jean-François Soulé, Henri Doucet. Palladium-Catalyzed Regioselective Direct Arylation of Benzofurazans at the C-4 Position. Advanced Synthesis and Catalysis, 2017, 359 (14), pp.2448-2456. ⟨10.1002/adsc.201700435⟩. ⟨hal-01578528⟩