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Synthesis of Trisubstituted Pyridines via Chemoselective Suzuki-Miyaura Coupling of 3,5-and 4,6-Dibromo-2-tosyloxypyridines
- Synthesis of Trisubstituted Pyridines via Chemoselective Suzuki-Miyaura Coupling of 3,5-and 4,6-Dibromo-2-tosyloxypyridines
- Park, Cho-Hee; Kwon, Yong-Ju; Oh, In-Young; Kim, Won-Suk
- Ewha Authors
- SCOPUS Author ID
- Issue Date
- Journal Title
- ADVANCED SYNTHESIS & CATALYSIS
- 1615-4150; 1615-4169
- vol. 359, no. 1, pp. 107 - 119
- chemoselective Suzuki-Miyaura reaction; copper-free Sonogashira reaction; ficuseptine; palladium-catalyzed amination; trisubstituted pyridines
- WILEY-V C H VERLAG GMBH
- SCI; SCIE; SCOPUS
- 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.
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