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

Eur. J. Org. Chem. 2018, 47, 6682-6692

DOI: 10.1002/ejoc.201801270

Cherepakha A.; Stepannikova K.; Vashchenko B.; Gorichko M.; Tolmachev A.; Grygorenko O.

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.

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

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