Use of a Readily Removable Auxiliary Group for the Synthesis of Pyrrolidones by the Palladium-Catalyzed Intramolecular Amination of Unactivated γ C(sp3)[BOND]H Bonds

Authors

  • Dr. Gang He,

    1. Department of Chemistry, The Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802 (USA)
    Search for more papers by this author
  • Dr. Shu-Yu Zhang,

    1. Department of Chemistry, The Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802 (USA)
    Search for more papers by this author
  • William A. Nack,

    1. Department of Chemistry, The Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802 (USA)
    Search for more papers by this author
  • Dr. Qiong Li,

    1. Department of Chemistry, The Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802 (USA)
    Search for more papers by this author
  • Prof. Dr. Gong Chen

    Corresponding author
    1. Department of Chemistry, The Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802 (USA)
    • Department of Chemistry, The Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802 (USA)

    Search for more papers by this author

  • We gratefully acknowledge The Pennsylvania State University, the NSF (CAREER CHE-1055795), and ACS-PRF (51705-DN11) for financial support of this research.

Abstract

original image

Easy on, easy off: Directing groups found to promote the palladium-catalyzed amination of γ C(sp3)[BOND]H and C(sp2)[BOND]H bonds of secondary amides included 5-methoxy-8-aminoquinoline, which can be removed under mild conditions (see scheme; CAN=ceric ammonium nitrate). In conjunction with a β-C[BOND]H methylation or γ-C[BOND]H arylation step, the γ-C(sp3)[BOND]H amination provided access to complex pyrrolidones from readily available precursors.

Ancillary