Phosphine-Based Redox Catalysis in the Direct Traceless Staudinger Ligation of Carboxylic Acids and Azides

Authors

  • Andrew D. Kosal,

    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.

  • 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 Prof. Xavier Creary for helpful discussions. Financial support for this work was received from the NSF (CHE-1056242) and the University of Notre Dame.

Abstract

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Redox catalysis: Aryl amides, imides, lactams, and dipeptides are obtained through a direct Staudinger ligation mediated by phosphine-based redox catalysis (see scheme). Mechanistic studies indicate the involvement of a phosphonium carboxylate intermediate that leads to a 1,3-acyl migration and thus results in C[BOND]N bond formation.

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