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A Versatile Catalyst-Free Perfluoroaryl Azide-Aldehyde-Amine Conjugation Reaction.


ABSTRACT: A tri-component reaction, involving an electrophilically-activated perfluoroaryl azide, an enolizable aldehyde and an amine, reacts 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 synthesize antibiotic-nanoparticle conjugates.

SUBMITTER: Xie S 

PROVIDER: S-EPMC6754110 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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A Versatile Catalyst-Free Perfluoroaryl Azide-Aldehyde-Amine Conjugation Reaction.

Xie Sheng S   Zhou Juan J   Chen Xuan X   Kong Na N   Fan Yanmiao Y   Zhang Yang Y   Hammer Gerry G   Castner David G DG   Ramström Olof O   Yan Mingdi M  

Materials chemistry frontiers 20181204 2


A tri-component reaction, involving an electrophilically-activated perfluoroaryl azide, an enolizable aldehyde and an amine, reacts 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 synthesize antibiotic-nanoparticle conjugates. ...[more]

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