Efficient Synthesis of N-2-Aryl-1,2,3-Triazole Fluorophores via Post-Triazole Arylation

Efficient post-triazole regioselective N-2 arylation was developed from C-4, C-5 disubstituted-1,2,3-NH-triazoles. Three different approaches had been investigated, including SNAr, Cu(I) catalyzed aryl amidation and Cu(II) mediated boronic acid coupling. The N-2-aryl triazoles were successfully synt...

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Bibliographic Details
Published in:Organic letters 2008-12, Vol.10 (23), p.5389-5392
Main Authors: Liu, Yuxiu, Yan, Wuming, Chen, Yunfeng, Petersen, Jeffrey L, Shi, Xiaodong
Format: Article
Language:English
Subjects:
Amides - chemistry
Catalysis
Copper - chemistry
Photons
Spectrometry, Fluorescence
Stereoisomerism
Substrate Specificity
Triazoles - chemical synthesis
Triazoles - chemistry
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Summary:Efficient post-triazole regioselective N-2 arylation was developed from C-4, C-5 disubstituted-1,2,3-NH-triazoles. Three different approaches had been investigated, including SNAr, Cu(I) catalyzed aryl amidation and Cu(II) mediated boronic acid coupling. The N-2-aryl triazoles were successfully synthesized with excellent yields. The structures were characterized by X-ray crystallography and some N-2-triazole products gave strong fluorescence with various emission controlled by the C-5 groups.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol802246q