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A Fluorogenic 1,3-Dipolar Cycloaddition Reaction of 3-Azidocoumarins and Acetylenes
Organic Letters · 2004 · Vol. 6(24) · pp. 4603–4606
K. Sivakumar✉(University of South Carolina Sumter)Fang Xie(University of South Carolina Sumter)Brandon Cash(University of South Carolina Sumter)Su Long(University of South Carolina Sumter)Hannah N. Barnhill(University of South Carolina Sumter)Qian Wang(University of South Carolina Sumter)
Abstract
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. [reaction: see text]
Click Chemistry and ApplicationsChemical Synthesis and AnalysisSynthesis and Catalytic ReactionsChemistryCycloaddition1,3-Dipolar cycloadditionCombinatorial chemistryOrganic chemistryComputational chemistryPhotochemistryCatalysis
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References
Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides
The Journal of Organic Chemistry · 2002 · 8,416 citations
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Angewandte Chemie International Edition · 2002 · 11,380 citations
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