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Palladium‐Catalyzed Buchwald–Hartwig Coupling of Deactivated Aminothiophenes with Substituted Halopyridines
Author(s) -
Begouin Agathe,
Hesse Stéphanie,
Queiroz MariaJoão R. P.,
Kirsch Gilbert
Publication year - 2007
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.200600951
Subject(s) - chemistry , xantphos , aryl , pyridine , palladium , borylation , thiophene , medicinal chemistry , suzuki reaction , catalysis , stille reaction , combinatorial chemistry , organic chemistry , alkyl
The palladium‐catalyzed Buchwald–Hartwig coupling of several deactivated aminothiophenecarboxylates with differently substituted halopyridines has been performed for the first time by using Pd(OAc) 2 , Xantphos as the ligand, and Cs 2 CO 3 as the base. When 2,6‐dihalopyridines were used, the proportion of diaminated product increases with the reactivity of the halopyridines (iodo > bromo > chloro). A bromo monoaminated pyridine derivative, obtained by Buchwald–Hartwig coupling, was further used in the Suzuki coupling of aryl boronic acids bearing electron‐withdrawing or electron‐donating groups. These latter compounds are very interesting as they possess diheteroarylamine and heteroaryl–aryl skeletons including pyridine and thiophene moieties.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)