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

Chem Commun (Camb)

Institut Lavoisier de Versailles, UMR 8180, Université de Versailles St-Quentin-en-Yvelines, Université Paris-Saclay. 45, av. des Etats-Unis, 78035 Versailles Cedex, France.

Published: December 2016

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.

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http://dx.doi.org/10.1039/c6cc08294gDOI Listing

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