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Issue 2, 2017
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A one carbon staple for orthogonal copper-catalyzed azide–alkyne cycloadditions

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Abstract

We describe herein the use of α-hydroxy-β-azidotetrazoles, easily prepared in one step from α,β-epoxynitriles, as new scaffolds for orthogonal CuAAC reactions performed on the same carbon atom. After a first ligation involving an alkyne with the β-azido moiety, treatment with EDC smoothly releases an alkyne from the remaining α-hydroxytetrazole, ready for a second CuAAC reaction. This “double click” process can be performed iteratively, leading to triazolamers.

Graphical abstract: A one carbon staple for orthogonal copper-catalyzed azide–alkyne cycloadditions

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Supplementary files

Article information


Submitted
14 Oct 2016
Accepted
01 Dec 2016
First published
01 Dec 2016

Chem. Commun., 2017,53, 321-323
Article type
Communication

A one carbon staple for orthogonal copper-catalyzed azide–alkyne cycloadditions

K. Wright, P. Quinodoz, B. Drouillat and F. Couty, Chem. Commun., 2017, 53, 321
DOI: 10.1039/C6CC08294G

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