Synthesis of Trisubstituted Pyridines via Chemoselective Suzuki-Miyaura Coupling of 3,5-and 4,6-Dibromo-2-tosyloxypyridines
- 주제(키워드) chemoselective Suzuki-Miyaura reaction , copper-free Sonogashira reaction , ficuseptine , palladium-catalyzed amination , trisubstituted pyridines
- 등재 SCIE, SCOPUS
- 발행기관 WILEY-V C H VERLAG GMBH
- 발행년도 2017
- 총서유형 Journal
- URI http://www.dcollection.net/handler/ewha/000000141973
- 본문언어 영어
- Published As http://dx.doi.org/10.1002/adsc.201600950
초록/요약
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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