A General Strategy for the Perfluoroalkylation of Arenes and Arylbromides by Using Arylboronate Esters and [(phen)CuRF]

Authors

  • Dr. Nichole D. Litvinas,

    1. Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA)
    2. Department of Chemistry, University of Illinois, Urbana-Champaign, Urbana, IL 61801 (USA)
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  • Patrick S. Fier,

    1. Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA)
    2. Department of Chemistry, University of Illinois, Urbana-Champaign, Urbana, IL 61801 (USA)
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  • Prof. Dr. John F. Hartwig

    Corresponding author
    1. Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA)
    2. Department of Chemistry, University of Illinois, Urbana-Champaign, Urbana, IL 61801 (USA)
    • Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA)
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  • We thank the NIH for funding (GM-58108 to J.F.H. and 1F32M093540-01 to N.D.L.). Carl Liskey is acknowledged for helpful discussions. phen=phenanthroline; RF=perfluoroalkylated residue

Abstract

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A versatile method for the synthesis of aryl perfluoroalkanes from arenes and aryl bromides is described. Substituted arenes or aryl bromides are converted in situ to an aryl boronate ester that readily undergoes perfluoroalkylation in air with [(phen)CuRF]. A broad range of aryl bromide substrates were perfluoroalkylated in good yield for the first time. [(phen)CuCF3] is now commercially available and has been prepared on 20 g scale.

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