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

2004686 citationsJournal Article

Authors

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]

Topics & Keywords

Click Chemistry and Applications Chemical Synthesis and Analysis Synthesis and Catalytic Reactions

UN Sustainable Development Goals

Clean water and sanitation

Publication Details

Published in: Organic Letters

Volume 6, Issue 24, pp. 4603-4606

DOI: 10.1021/ol047955x

Field-Weighted Citation Impact: 11.16