Issue 37, 2013

Recent advances in the Cu(i)-catalyzed azide–alkyne cycloaddition: focus on functionally substituted azides and alkynes

Abstract

First described by the groups of Sharpless (Rostovtsev et al., Angew. Chem., Int. Ed., 2002, 41, 2596) and Meldal (Tornøe et al., J. Org. Chem., 2002, 67, 3057) in 2002, Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) became one of the most effective and reliable synthetic tools in diverse areas of modern chemistry, such as organic, medicinal and polymer chemistry, material science and chemical biology. The advantages of this reaction are high selectivity, simple reaction conditions, wide scope and excellent functional group tolerance. This efficient transformation can be used for the synthesis of various 1,2,3-triazoles. On the other hand, CuAAC can be efficiently used for bioconjugation of two units bearing alkyne and azide functions via the triazole moiety. Moreover, the use of azides and alkynes bearing orthogonal functional groups in this reaction opens broad opportunities for the synthesis of valuable polyfunctionalized triazole-containg molecules. Thus, the initial discussion is focused on synthetic applications of functionally substituted azides and terminal alkynes in the CuAAC, combined with other transformations. The prominent part of this review is devoted to an application of these bi (or tri)-functional reagents for the design, synthesis or labeling of biologically active molecules.

Graphical abstract: Recent advances in the Cu(i)-catalyzed azide–alkyne cycloaddition: focus on functionally substituted azides and alkynes

Article information

Article type
Review Article
Submitted
10 رجب 1434
Accepted
15 شعبان 1434
First published
16 شعبان 1434

RSC Adv., 2013,3, 16212-16242

Recent advances in the Cu(I)-catalyzed azide–alkyne cycloaddition: focus on functionally substituted azides and alkynes

N. V. Sokolova and V. G. Nenajdenko, RSC Adv., 2013, 3, 16212 DOI: 10.1039/C3RA42482K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements