Journal
RSC ADVANCES
Volume 6, Issue 6, Pages 4608-4621Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ra21701f
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- Scientific and Technological Research Council of Turkey (TUBITAK) [110T113]
- Middle East Technical University (METU) [BAP-2011-07-02-00-01]
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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.
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