Chemoselective Sequential Click Ligations Directed by Enhanced Reactivity of an Aromatic Ynamine

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• 作者：Marine Z. C. Hatit ; Joanna C. Sadler ; Liam A. McLean ; Benjamin C. Whitehurst ; Ciaran P. Seath ; Luke D. Humphreys ; Robert J. Young ; Allan J. B. Watson ; Glenn A. Burley
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：April 1, 2016
• 年：2016
• 卷：18
• 期：7
• 页码：1694-1697
• 全文大小：347K
• ISSN：1523-7052

文摘

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.