A Fluorogenic 1,3-Dipolar Cycloaddition Reaction of 3-Azidocoumarins and Acetylenes

Copper(I)-catalyzed 1,3-dipolar cycloaddition reaction of nonfluorescent 3-azidocoumarins and terminal alkynes afforded intense fluorescent 1,2,3-triazole products. The mild condition of this reaction allowed us to construct a large library of pure fluorescent coumarin dyes. Since both azide and alk...

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Bibliographic Details
Published in:Organic letters 2004-11, Vol.6 (24), p.4603-4606
Main Authors: Sivakumar, Krishnamoorthy, Xie, Fang, Cash, Brandon M, Long, Su, Barnhill, Hannah N, Wang, Qian
Format: Article
Language:English
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Summary:Copper(I)-catalyzed 1,3-dipolar cycloaddition reaction of nonfluorescent 3-azidocoumarins and terminal alkynes afforded intense fluorescent 1,2,3-triazole products. The mild condition of this reaction allowed us to construct a large library of pure fluorescent coumarin dyes. Since both azide and alkyne are quite inert to biological systems, this reaction has potential in bioconjugation and bioimaging applications.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol047955x