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Synthesis of Macrocyclic Tetrazoles for Rapid Photoinduced Bioorthogonal 1,3-Dipolar Cycloaddition Reactions

Authors

  • Dr. Zhipeng Yu,

    1. Department of Chemistry, State University of New York at Buffalo, Buffalo, NY 14260 (USA), Fax: (+1) 716-645-6963
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  • Reyna K. V. Lim,

    1. Department of Chemistry, State University of New York at Buffalo, Buffalo, NY 14260 (USA), Fax: (+1) 716-645-6963
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  • Prof. Dr. Qing Lin

    Corresponding author
    1. Department of Chemistry, State University of New York at Buffalo, Buffalo, NY 14260 (USA), Fax: (+1) 716-645-6963
    • Department of Chemistry, State University of New York at Buffalo, Buffalo, NY 14260 (USA), Fax: (+1) 716-645-6963
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Abstract

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Quick as a flash! A series of conformationally constrained, macrocyclic tetrazoles were expediently prepared by double alkylation of a bis(o-phenolyl)tetrazole precursor. Several of them showed excellent reactivity toward norbornene in a photoinduced tetrazole–alkene cycloaddition reaction in organic solvent, as well as toward a norbornene-modified protein in phosphate-buffered saline buffer (see scheme).

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