Chemoselective Sequential "Click" Ligation Using Unsymmetrical Bisazides

被引：69

作者：

Yuan, Zhao ^{[1
]}

Kuang, Gui-Chao ^{[1
]}

Clark, Ronald J. ^{[1
]}

Zhu, Lei ^{[1
]}

机构：

[1] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 10期

基金：

美国国家科学基金会;

关键词：

ONE-POT; CHEMISTRY; MECHANISM;

D O I：

10.1021/ol300899n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unsymmetrical bisazides containing chelating and nonchelating azido groups undergo chemoselective three-component copper(I)-catalyzed azide-alkyne conjugation reactions with two different alkyne molecules. In conjunction with the reactivity gap between aromatic and aliphatic alkynes, a bistriazole molecule can be generated with excellent regioselectivity by mixing two alkynes and a bisazide in a single reaction container. This method is applicable in aqueous solutions at neutral pH, which may lend utilities in bioconjugation applications.

引用

页码：2590 / 2593

页数：4

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