Copper-Catalyzed Synthesis of N-Sulfonyl-1,2,3-triazoles: Controlling Selectivity

Authors

  • Eun Jeong Yoo,

    1. Center for Molecular Design and Synthesis (CMDS), Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology (KAIST), Daejon 305-701, Korea, Fax: (+82) 42-869-2810
    Search for more papers by this author
  • Mårten Ahlquist,

    1. Department of Chemistry, Building 201, Kemitorvet, Technical University of Denmark, 2888 Lyngby, Denmark
    Search for more papers by this author
  • Seok Hwan Kim,

    1. Center for Molecular Design and Synthesis (CMDS), Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology (KAIST), Daejon 305-701, Korea, Fax: (+82) 42-869-2810
    Search for more papers by this author
  • Imhyuck Bae Dr.,

    1. Center for Molecular Design and Synthesis (CMDS), Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology (KAIST), Daejon 305-701, Korea, Fax: (+82) 42-869-2810
    Search for more papers by this author
  • Valery V. Fokin Prof. Dr.,

    1. Department of Chemistry and The Skaggs Institute of Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7562
    Search for more papers by this author
  • K. Barry Sharpless Prof. Dr.,

    1. Department of Chemistry and The Skaggs Institute of Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7562
    Search for more papers by this author
  • Sukbok Chang Prof. Dr.

    1. Center for Molecular Design and Synthesis (CMDS), Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology (KAIST), Daejon 305-701, Korea, Fax: (+82) 42-869-2810
    Search for more papers by this author

  • This research was supported by LG Yonam Foundation and CMDS at KAIST.

Abstract

original image

4-Substituted 1-(N-sulfonyl)-1,2,3-triazoles are selectively obtained by using the Cu-catalyzed azide–alkyne cycloaddition reaction with sulfonyl azides. Performing the reaction at 0 °C in chloroform in the presence of 2,6-lutidine and CuI as the catalyst effectively prevents the ketenimine pathway and provides convenient access to N-sulfonyltriazoles in good to excellent yields.

Ancillary