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

Cho Hee Park, Yong Ju Kwon, In Young Oh, Won Suk Kim

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

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 trisubstituted 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. (Figure presented.).

Original languageEnglish
Pages (from-to)107-119
Number of pages13
JournalAdvanced Synthesis and Catalysis
Volume359
Issue number1
DOIs
StatePublished - 4 Jan 2017

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) (NRF-2015R1A1A1A05001334) and the New & Renewable Energy of the Korea Institute of Energy Technology Evaluation and Planning (KETEP) (grant No. 20163030013900).

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • chemoselective Suzuki–Miyaura reaction
  • copper-free Sonogashira reaction
  • ficuseptine
  • palladium-catalyzed amination
  • trisubstituted pyridines

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