Hetaryl Bromides Bearing SO₂F Group - Versatile Substrates for Palladium-Catalyzed C-C Coupling Reactions

Synthesis of novel five‐ and six‐membered heteroaromatic sulfonyl fluorides bearing bromine atom at various positions of the heterocyclic ring is described. Synthetic utility of these compounds is demonstrated by the Suzuki, Stille and Negishi cross‐coupling reactions, which proceeded chemoselectively at the aryl bromide moiety with 69–98% yields. Tolerance of the SO₂F group towards the coupling reaction conditions was confirmed in most experiments. The proposed method was efficient for either sp²–sp² or sp²–sp³ C–C couplings. The developed procedure provides rapid access to various substituted heterocyclic sulfonyl fluorides.