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A Bulky Biaryl Phosphine Ligand Allows for Palladium-Catalyzed Amidation of Five-Membered Heterocycles as Electrophiles

Authors

  • Mingjuan Su,

    1. Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA 02139 (USA)
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  • Prof. Dr. Stephen L. Buchwald

    Corresponding author
    1. Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA 02139 (USA)
    • Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA 02139 (USA)
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  • This work was supported by an educational domain provided by Amgen and by funds from the National Institutes of Health (GM58160). We thank Dr. Thomas J. Maimone and Dr. Satoshi Ueda for helpful discussions and Dr. Meredeth A. McGowan for help with preparation of this manuscript. The Varian 300 MHz NMR spectrometer used for portions of this work was supported by the National Science Foundation (Grants CHE9808061 and DBI9729592). The departmental X-ray diffraction instrumentation was purchased with the help of funding from the National Science Foundation (CHE-0946721).

Abstract

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Reich und anspruchsvoll: Die erste Palladium-katalysierte Amidierung von fünfgliedrigen heterocyclischen Bromiden mit mehreren Heteroatomen wurde mit dem Katalysatorsystem Pd/1 erzielt (siehe Schema). N-arylierte Imidazole, Pyrazole, Thiazole, Pyrrole und Thiophene wurden in mittleren bis sehr guten Ausbeuten synthetisiert. Experimentelle Ergebnisse und DFT-Rechnungen besagen, dass ein elektronenreicher und sterisch anspruchsvoller Biarylphosphanligand nötig ist, um diese schwierigen Reaktionen ablaufen zu lassen.

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