Chemoselective sequential "click" ligation using unsymmetrical bisazides

Organic Letters
Zhao YuanLei Zhu

Abstract

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.

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Citations

Aug 16, 2015·Current Opinion in Chemical Biology·David M Patterson, Jennifer A Prescher
Oct 5, 2016·Journal of the American Chemical Society·James E M LewisStephen M Goldup
Feb 14, 2017·Chemistry : a European Journal·Haoqing ChenZhiling Zhu
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