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Amine-Free Approach toward N-Toluenesulfonyl Amidine Construction: A Phosphite-Mediated Beckmann-Like Coupling of Oximes and p-Toluenesulfonyl Azide

Authors

  • Lauren M. Fleury,

    1. Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556 (USA)
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    • These authors contributed equally to this work.

  • Erin E. Wilson,

    1. Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556 (USA)
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    • These authors contributed equally to this work.

  • Monika Vogt,

    1. Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556 (USA)
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  • Tiffany J. Fan,

    1. Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556 (USA)
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  • Allen G. Oliver,

    1. Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556 (USA)
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  • Prof. Dr. Brandon L. Ashfeld

    Corresponding author
    1. Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556 (USA)
    • Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556 (USA)

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  • We thank the NSF (CHE-1056242) and the University of Notre Dame for financial support, including the purchase of a copper microfocus source used in this research.

Abstract

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Atom hopping: A chlorophosphite-mediated Beckmann ligation of oximes and p-toluenesulfonyl azide gives access to N-sulfonyl phosphoramidines in good to excellent yields. The reaction proceeds under exceptionally mild conditions and constitutes a bioorthogonal approach toward amidines by avoiding the use of amines and transition-metal catalysts. dmp-ol=3,3-dimethylpropanediol.

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