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Highly Selective Room-Temperature Suzuki-Miyaura Coupling of Bromo-2-sulfonyloxypyridines for Unsymmetrical Diarylpyridines
- Title
- Highly Selective Room-Temperature Suzuki-Miyaura Coupling of Bromo-2-sulfonyloxypyridines for Unsymmetrical Diarylpyridines
- Authors
- Jeon, Young-Kyo; Lee, Jae-Yeon; Kim, Seo-Eun; Kim, Won-Suk
- Ewha Authors
- 김원석
- SCOPUS Author ID
- 김원석
- Issue Date
- 2020
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- ISSN
- 0022-3263
1520-6904
- Citation
- JOURNAL OF ORGANIC CHEMISTRY vol. 85, no. 11, pp. 7399 - 7412
- Publisher
- AMER CHEMICAL SOC
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- Abstract
- A new and mild synthetic approach has been developed for the synthesis of pharmaceutically important unsymmetrical diarylpyridines via chemoselective Suzuki-Miyaura coupling reactions of bromo-2-sulfonyloxypyridines. Most reactions allow for facile access to aryl-2-sulfonyloxypyridines at room temperature in yields of 5-99% with excellent chemoselectivity in the presence of Pd(OAc)(2) (2.0 mol %) and Ad(2)BnP (2.4 mol %). The second arylation of the remaining tosyl or triflyl group in the monoarylpyridine derivatives obtained was successfully accomplished for the synthesis of unsymmetrical 2,3-, 2,4-, 2,5-, and 2,6-diarylpyridine derivatives. Furthermore, a one-pot synthesis of unsymmetrical diarylpyridines starting from bromo-2-sulfonyloxypyridine was accomplished to demonstrate the practical convenience. Finally, with this method, an antibacterial agent, a topoisomerase inhibitor, and etoricoxib, a nonsteroidal anti-inflammatory drug, were successfully synthesized from the corresponding bromo-2-hydroxypyridines in overall yields of 80, 86, and 49%, respectively.
- DOI
- 10.1021/acs.joc.0c00793
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
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