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Pd-Catalyzed Aryl Amination Mediated by Well Defined, N-Heterocyclic Carbene (NHC)–Pd Precatalysts, PEPPSI

Authors

  • Michael G. Organ Prof.,

    1. Chemistry Department, York University, 4700 Keele Street, Toronto, M3J 1P3, Canada, Fax: (+1) 416-736-2100
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  • Mirvat Abdel-Hadi,

    1. Chemistry Department, York University, 4700 Keele Street, Toronto, M3J 1P3, Canada, Fax: (+1) 416-736-2100
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  • Stephanie Avola,

    1. Chemistry Department, York University, 4700 Keele Street, Toronto, M3J 1P3, Canada, Fax: (+1) 416-736-2100
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  • Igor Dubovyk,

    1. Chemistry Department, York University, 4700 Keele Street, Toronto, M3J 1P3, Canada, Fax: (+1) 416-736-2100
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  • Niloufar Hadei,

    1. Chemistry Department, York University, 4700 Keele Street, Toronto, M3J 1P3, Canada, Fax: (+1) 416-736-2100
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  • Eric Assen B. Kantchev Dr.,

    1. Chemistry Department, York University, 4700 Keele Street, Toronto, M3J 1P3, Canada, Fax: (+1) 416-736-2100
    2. Present address: Institute of Bioengineering and Nanotechnology, 31 Biopolis Way #04-01 The Nanos, Singapore 138669
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  • Christopher J. O'Brien Dr.,

    1. Chemistry Department, York University, 4700 Keele Street, Toronto, M3J 1P3, Canada, Fax: (+1) 416-736-2100
    2. Present address: The Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, Texas, 76019, USA
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  • Mahmoud Sayah,

    1. Chemistry Department, York University, 4700 Keele Street, Toronto, M3J 1P3, Canada, Fax: (+1) 416-736-2100
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  • Cory Valente

    1. Chemistry Department, York University, 4700 Keele Street, Toronto, M3J 1P3, Canada, Fax: (+1) 416-736-2100
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  • PEPPSI: pyridine, enhanced, precatalyst, preparation, stabilization, and initiation

Abstract

Pd–N-heterocyclic carbene (NHC)-catalyzed Buchwald–Hartwig amination protocols mediated by Pd–PEPPSI precatalysts is described. These protocols provide access to a range of hindered and functionalized drug-like aryl amines in high yield with both electron-deficient and electron-rich aryl- and heteroaryl chlorides and bromides. Variations in solvent polarity, base and temperature are tolerated, enhancing the scope and utility of this protocol. A mechanistic rationalization for base strength (pKb) requirements is also provided.

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