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Synthesis of Trisubstituted Pyridines via Chemoselective Suzuki-Miyaura Coupling of 3,5-and 4,6-Dibromo-2-tosyloxypyridines

Title
Synthesis of Trisubstituted Pyridines via Chemoselective Suzuki-Miyaura Coupling of 3,5-and 4,6-Dibromo-2-tosyloxypyridines
Authors
Park, Cho-HeeKwon, Yong-JuOh, In-YoungKim, Won-Suk
Ewha Authors
김원석
SCOPUS Author ID
김원석scopus
Issue Date
2017
Journal Title
ADVANCED SYNTHESIS & CATALYSIS
ISSN
1615-4150JCR Link1615-4169JCR Link
Citation
vol. 359, no. 1, pp. 107 - 119
Keywords
chemoselective Suzuki-Miyaura reactioncopper-free Sonogashira reactionficuseptinepalladium-catalyzed aminationtrisubstituted pyridines
Publisher
WILEY-V C H VERLAG GMBH
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
Chemoselective Suzuki-Miyaura reactions on 3,5-and 4,6-dibromo-2-tosyloxypyridines have been studied for the preparation of trisubstituted pyridines. The optimized conditions allow for a facile access to 3,5-and 4,6-diaryl-2-tosyloxypyridines in yields of 8 to 99%. Further functionalization such as palladium-catalyzed amination and copper-free Sonogashira reaction of the tosylate group in the diarylpyridine derivatives obtained was accomplished for the synthesis of novel and biologically relevant tri-substituted pyridines. The formal synthesis of ficuseptine, a bioactive alkaloid, has also been achieved via the palladium-catalyzed cross-coupling reaction of 3,5-dibromo-2-tosyloxypyridine in 5 steps from 3,5-dibromo-2-hydroxypyridine with 50% overall yield.
DOI
10.1002/adsc.201600950
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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