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Chemoselective sequential click ligations directed by enhanced reactivity of an aromatic ynamine

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Original languageEnglish
Pages (from-to)1694-1697
JournalOrganic letters
Volume18
Issue number7
Early online date22 Mar 2016
DOIs
Publication statusPublished - 1 Apr 2016

Abstract

Aromatic ynamines or N-alkynylheteroarenes are highly reactive alkyne components in Cu-catalyzed Huisgen [3 + 2] cycloaddition (“click”) reactions. This enhanced reactivity enables the chemoselective formation of 1,4-triazoles using the representative aromatic ynamine N-ethynylbenzimidazole in the presence of a competing aliphatic alkyne substrate. The unique chemoselectivity profile of N-ethynylbenzimidazole is further demonstrated by the sequential click ligation of a series of highly functionalized azides using a heterobifunctional diyne, dispelling the need for alkyne protecting groups.

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