A one carbon staple for orthogonal copper-catalyzed azide–alkyne cycloadditions. Issue 2 (8th December 2016)

• Record Type: Journal Article
• Authors: Wright, Karen; Quinodoz, Pierre; Drouillat, Bruno; Couty, François
• Is Part Of: Chemical communications. Volume 53:Issue 2(2017)
• Page Start: 321
• Page End: 323
• Publication Date: 2016-12-08
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c6cc08294g
• Languages: English
• ISSNs: 1359-7345

Abstract

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. 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.