Issue 4, 2010

The application of CuAAC ‘click’ chemistry to catenane and rotaxane synthesis

Abstract

The copper(I)-catalysed azidealkyne cycloaddition (the CuAAC ‘click’ reaction) is proving to be a powerful new tool for the construction of mechanically interlocked molecular-level architectures. The reaction is highly selective for the functional groups involved (terminal alkynes and azides) and the experimental conditions are mild and compatible with the weak and reversible intermolecular interactions generally used to template the assembly of interlocked structures. Since the CuAAC reaction was introduced as a means of making rotaxanes by an ‘active template’ mechanism in 2006, it has proven effective for the synthesis of numerous different types of rotaxanes, catenanes and molecular shuttles by passive as well as active template strategies. Mechanistic insights into the CuAAC reaction itself have been provided by unexpected results encountered during the preparation of rotaxanes. In this tutorial review we highlight the rapidly increasing utility and future potential of the CuAAC reaction in mechanically interlocked molecule synthesis.

Graphical abstract: The application of CuAAC ‘click’ chemistry to catenane and rotaxane synthesis

Article information

Article type
Tutorial Review
Submitted
01 Sep 2009
First published
16 Nov 2009

Chem. Soc. Rev., 2010,39, 1240-1251

The application of CuAAC ‘click’ chemistry to catenane and rotaxane synthesis

K. D. Hänni and D. A. Leigh, Chem. Soc. Rev., 2010, 39, 1240 DOI: 10.1039/B901974J

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