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Issue 4, 2010
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The application of CuAAC ‘click’ chemistry to catenane and rotaxane synthesis

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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

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Publication details

The article was received on 01 Sep 2009 and first published on 16 Nov 2009


Article type: Tutorial Review
DOI: 10.1039/B901974J
Citation: Chem. Soc. Rev., 2010,39, 1240-1251
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    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

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