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Hetaryl Bromides Bearing the SO 2 F Group – Versatile Substrates for Palladium‐Catalyzed C–C Coupling Reactions
Author(s) -
Cherepakha Artem Yu.,
Stepannikova Kateryna O.,
Vashchenko Bohdan V.,
Gorichko Marian V.,
Tolmachev Andrey A.,
Grygorenko Oleksandr O.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801270
Subject(s) - chemistry , stille reaction , negishi coupling , sulfonyl , palladium , bromide , moiety , aryl , bromine , ring (chemistry) , coupling reaction , catalysis , functional group , medicinal chemistry , combinatorial chemistry , organic chemistry , alkyl , polymer
Synthesis of novel five‐ and six‐membered heteroaromatic sulfonyl fluorides bearing bromine atom at various positions of the heterocyclic ring is described. The 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. The tolerance of the SO 2 F group towards the coupling reaction conditions was confirmed in most of the experiments. The proposed method was efficient for either sp 2 –sp 2 or sp 2 –sp 3 C–C couplings. The developed procedure provides rapid access to various substituted heterocyclic sulfonyl fluorides.