Facile synthesis of heavily-substituted alkynylpyridines via a Sonogashira approach
RSC ADVANCES, cilt.6, ss.4608-4621, 2016 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 6
- Basım Tarihi: 2016
- Doi Numarası: 10.1039/c5ra21701f
- Dergi Adı: RSC ADVANCES
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.4608-4621
- Orta Doğu Teknik Üniversitesi Adresli: Evet
Özet
A facile and efficient synthetic route to densely substituted alkynylpyridines via a Sonogashira approach is reported. When treated with terminal alkynes in the presence of 5 mol% PdCl2(PPh3)(2), 5 mol% CuI and excess Et3N in DMF at 65 degrees C, iodopyridines underwent Sonogashira coupling to afford alkynyl-substituted pyridines in good to excellent yields. The coupling reaction has been found to be general for a wide range of iodopyridines and terminal alkynes, and tolerated the presence of aliphatic, aromatic, heteroaromatic and ferrocenyl groups with electron-withdrawing and electron-donating substituents. This coupling approach could allow for the rapid construction of a library of functionalized alkynylpyridines of pharmacological interest.