Please use this identifier to cite or link to this item:
|Title:||Microwave-assisted palladium-catalyzed C-C coupling versus nucleophilic aromatic substitution of hydrogen (SN H) in 5-bromopyrimidine by action of bithiophene and its analogues|
|Authors:||Verbitskiy, E. V.|
Cheprakova, E. M.
Zhilina, E. F.
Kodess, M. I.
Ezhikova, M. A.
Pervova, M. G.
Slepukhin, P. A.
Subbotina, J. O.
Schepochkin, A. V.
Rusinov, G. L.
Chupakhin, O. N.
Charushin, V. N.
|Citation:||Microwave-assisted palladium-catalyzed C-C coupling versus nucleophilic aromatic substitution of hydrogen (SN H) in 5-bromopyrimidine by action of bithiophene and its analogues / E. V. Verbitskiy, E. M. Cheprakova, E. F. Zhilina [et al.] // Tetrahedron. — 2013. — Vol. 69. — № 25. — P. 5164-5172.|
|Abstract:||5-Bromopyrimidine reacts with 2,2′-bithiophene, [2,2′:5′, 2″]terthiophene and 2-phenylthiophene in the presence of a palladium catalyst to give 5-(het)aryl substituted pyrimidines due to the palladium-catalyzed aryl-aryl C-C coupling. However 5-bromo-4-(het)aryl- pyrimidines have been prepared from the same starting materials through the SN H-reaction catalyzed by a Lewis acid. Conditions for both types of reactions were optimized. All components of the reaction mixtures, including by-products, have been elucidated by gas-liquid chromatography/mass- spectrometry. Evidence for the structure of 4- and 5-bithiophenyl-substituted pyrimidines has first been obtained by means of X-ray crystallography analysis. Molecular orbital calculations (TDDFT), as well as the redox and optical measurements for all new compounds have also been performed. © 2013 Elsevier Ltd. All rights reserved.|
|Keywords:||C-H BOND ACTIVATIONS|
NUCLEOPHILIC AROMATIC SUBSTITUTION OF HYDROGEN
X RAY CRYSTALLOGRAPHY
|Appears in Collections:||Научные публикации, проиндексированные в SCOPUS и WoS CC|
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.