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A versatile catalyst-free perfluoroaryl azide–aldehyde–amine conjugation reaction

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Abstract

In a tri-component reaction, an electrophilically-activated perfluoroaryl azide, an enolizable aldehyde and an amine react readily at room temperature without any catalysts in solvents including aqueous conditions to yield a stable amidine conjugate. The versatility of this reaction is demonstrated in the conjugation of an amino acid without prior protection of the carboxyl group, and in the synthesis of antibiotic–nanoparticle conjugates.

Graphical abstract: A versatile catalyst-free perfluoroaryl azide–aldehyde–amine conjugation reaction

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Publication details

The article was received on 10 Oct 2018, accepted on 30 Nov 2018 and first published on 04 Dec 2018


Article type: Research Article
DOI: 10.1039/C8QM00516H
Citation: Mater. Chem. Front., 2019, Advance Article
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    A versatile catalyst-free perfluoroaryl azide–aldehyde–amine conjugation reaction

    S. Xie, J. Zhou, X. Chen, N. Kong, Y. Fan, Y. Zhang, G. Hammer, D. G. Castner, O. Ramström and M. Yan, Mater. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QM00516H

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