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Synthesis of the 4,7‐Dibromo Derivative of Highly Electron‐Deficient [1,2,5]Thiadiazolo[3,4‐ d ]pyridazine and Its Cross‐Coupling Reactions
Author(s) -
Chmovzh Timofey N.,
Knyazeva Ekaterina A.,
Mikhalchenko Ludmila V.,
Golovanov Ivan S.,
Amelichev Stanislav A.,
Rakitin Oleg A.
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.201800961
Subject(s) - pyridazine , chemistry , stille reaction , homo/lumo , palladium , derivative (finance) , suzuki reaction , coupling reaction , acceptor , electron acceptor , medicinal chemistry , combinatorial chemistry , photochemistry , computational chemistry , organic chemistry , catalysis , molecule , physics , financial economics , economics , condensed matter physics
An efficient synthesis of 4,7‐dibromo[1,2,5]thiadiazolo[3,4‐ d ]pyridazine is reported. For the first time, palladium‐catalysed cross‐coupling reactions of a dihalo derivative was found to be a powerful tool for the selective formation of various mono‐ and diarylated derivatives of strongly electron‐accepting heterocycles. Suzuki–Miyaura coupling can be successfully employed for the preparation of mono‐arylated derivatives, whereas Stille coupling is useful for both mono‐ and diaryl(hetaryl)ated heterocycles. The cyclic voltammogram showed that 4,7‐dibromo[1,2,5]thiadiazolo[3,4‐ d ]pyridazine can be easily oxidized to form a stable anion radical. The calculated values of E LUMO confirmed that [1,2,5]thiadiazolo[3,4‐ d ]pyridazine is one of the strongest electron–acceptor systems.