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Efficiency and Fidelity in a Click-Chemistry Route to Triazole Dendrimers by the Copper(I)-Catalyzed Ligation of Azides and Alkynes

Authors

  • Peng Wu,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7562
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  • Alina K. Feldman,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7562
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  • Anne K. Nugent,

    1. IBM Almaden Research Center, 650 Harry Road, San Jose, CA 95120, USA, Fax: (+1) 408-927-3310
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  • Craig J. Hawker Dr.,

    1. IBM Almaden Research Center, 650 Harry Road, San Jose, CA 95120, USA, Fax: (+1) 408-927-3310
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  • Arnulf Scheel,

    1. IBM Almaden Research Center, 650 Harry Road, San Jose, CA 95120, USA, Fax: (+1) 408-927-3310
    2. Institut für Polymerforschung Dresden e.V. Hohe Strasse 6, 01069 Dresden, Germany
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  • Brigitte Voit Prof.,

    1. Institut für Polymerforschung Dresden e.V. Hohe Strasse 6, 01069 Dresden, Germany
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  • Jeffrey Pyun Dr.,

    1. IBM Almaden Research Center, 650 Harry Road, San Jose, CA 95120, USA, Fax: (+1) 408-927-3310
    2. University of California, Department of Chemistry and Materials Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720, USA
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  • Jean M. J. Fréchet,

    1. University of California, Department of Chemistry and Materials Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720, USA
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  • K. Barry Sharpless Prof.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7562
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  • Valery V. Fokin Prof.

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7562
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  • We thank the National Institute of General Medical Sciences, the National Institutes of Health (GM 28284), the National Science Foundation (CHE-9985553), the W. M. Keck Foundation, the Skaggs Institute for Chemical Biology, the MRSEC Program of the National Science Foundation (award no. DMR-0213618 for the Center for Polymeric Interfaces and Macromolecular Assemblies), the NIRT Program of the National Science Foundation (grant no. 0210247), IBM Corporation, DOE-BES, and NSF International/DAAD for financial support. We are also grateful to Prof. M. G. Finn for helpful discussions.

Abstract

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Components that click: A large number of diverse dendrimers (see scheme) was prepared in almost quantitative yield by the click-chemistry transformation described in the title. In some cases filtration or solvent extraction was the only method required for purification in this highly efficient construction of the triazole units of the dendrimers.

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