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Nucleophilic Addition to N-Phosphinylimines by Rare-Earth-Metal Triflate/Trifluoroacetic Anhydride Activation

Authors

  • Winnie W. Ong,

    1. Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847
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  • Aaron B. Beeler Dr.,

    1. Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847
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  • Sarathy Kesavan Dr.,

    1. Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847
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  • James S. Panek Prof. Dr.,

    1. Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847
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  • John A. Porco Jr. Prof. Dr.

    1. Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847
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  • This work was generously supported by the NIGMS CMLD initiative (P50 GM067041). We thank Professors Scott Schaus (Boston University) and Jinquan Yu (Brandeis University) for helpful discussions, Dr. Paul Ralifo (Boston University) for assistance with NMR structure elucidation, CEM Corporation (Matthews, NC) for assistance with microwave instrumentation, and Symyx Technologies, Inc. (Santa Clara, CA) for assistance with chemical reaction planning software.

Abstract

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Hydrated lanthanum triflate has been shown to be an effective and highly active Lewis acid catalyst for nucleophilic addition to N-phosphinylimines in the presence of trifluoroacetic anhydride (TFAA; see scheme). Unexpectedly, trifluoroacetamide products are produced in a novel process which likely involves consecutive acylation/hydration of N-phosphinylimine substrates and subsequent nucleophilic addition.

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