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Issue 6, 2016
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Facile synthesis of heavily-substituted alkynylpyridines via a Sonogashira approach

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Abstract

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 °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.

Graphical abstract: Facile synthesis of heavily-substituted alkynylpyridines via a Sonogashira approach

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Supplementary files

Article information


Submitted
17 Oct 2015
Accepted
22 Dec 2015
First published
23 Dec 2015

RSC Adv., 2016,6, 4608-4621
Article type
Paper

Facile synthesis of heavily-substituted alkynylpyridines via a Sonogashira approach

Y. Kelgokmen and M. Zora, RSC Adv., 2016, 6, 4608
DOI: 10.1039/C5RA21701F

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