Facile synthesis of aryl-substituted pyridines via Suzuki-Miyaura approach

Date

2015-11-25

Author

KARADENİZ, EDA
Zora, Metin
KILIÇASLAN, Nihan Zulay

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A facile and efficient synthetic route to arylpyridines is reported. When heated with boronic acids in the presence of 5 mol % PdCl2(PPh3)(2) and KHCO3 in 4:1 DMF/H2O solution at 110 degrees C, 5-iodopyridines have undergone Suzuki-Miyaura coupling reactions to afford 5-aryl-substituted pyridines in good to excellent yields. The coupling reaction has been found to be general for a broad range of iodopyridines and boronic acids, and demonstrated good tolerance to a variety of aliphatic, aromatic, heteroaromatic and ferrocenyl groups with electron-withdrawing and electron-donating substituents. This coupling approach could accommodate various functional groups and provide rapid access to a library of functionalized arylpyridines of pharmacological interest. The starting 5-iodopyridines have been prepared from alpha,beta-alkynic ketones, involving conjugate addition of propargylamine to alkynones, followed by metal-catalyzed cross-coupling of the resulting N-propargylic beta-enaminones with aryl iodides and electrophilic cyclization with molecular iodine.

Subject Keywords

Ferrocene, Suzuki-Miyaura reaction, Coupling, Iodopyridine, Arylpyridine, Pyridine, Pyridine

URI

https://hdl.handle.net/11511/43175

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2015.09.063

Collections

Department of Chemistry, Article

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Citation Formats

E. KARADENİZ, M. Zora, and N. Z. KILIÇASLAN, “Facile synthesis of aryl-substituted pyridines via Suzuki-Miyaura approach,” TETRAHEDRON, pp. 8943–8952, 2015, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/43175.