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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 7
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Original Articles

Chemical Labeling of 5-Iodo-2′-deoxyuridine with 4-Ethynyl-N-ethyl-1,8-naphthalimide Using Copper-Free Sonogashira Cross-Coupling in Aqueous Medium

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Pages 1007-1011 | Received 01 Jul 2013, Published online: 24 Feb 2014
 

Abstract

The utility of Sonogashira cross-coupling reactions in organic synthesis is indisputable. However, the palladium catalytic Sonogashira reaction in mild condition is still in its infancy. Here, we reported the synthesis of a fluorescent nucleoside analog by using a copper-free Sonogashira cross-coupling reaction in a satisfactory yield. This reaction occurred at 37 °C in the open air and aqueous medium, and avoided the toxicity of Cu(I). The mild Sonogashira reaction provided the possibility of fluorescent labeling of nucleoside mimics in living cells.

[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]

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