Iron-Catalyzed Nitrogen-Directed Coupling of Arene and Aryl Bromides Mediated by Metallic Magnesium

Authors

  • Laurean Ilies,

    1. Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81)-3-5800-6889; phone: (+81)-3-5800-6889
    Search for more papers by this author
  • Motoaki Kobayashi,

    1. Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81)-3-5800-6889; phone: (+81)-3-5800-6889
    Search for more papers by this author
  • Arimasa Matsumoto,

    1. Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81)-3-5800-6889; phone: (+81)-3-5800-6889
    Search for more papers by this author
  • Naohiko Yoshikai,

    1. Present Address: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
    Search for more papers by this author
  • Eiichi Nakamura

    Corresponding author
    1. Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81)-3-5800-6889; phone: (+81)-3-5800-6889
    • Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81)-3-5800-6889; phone: (+81)-3-5800-6889
    Search for more papers by this author

Abstract

2-Arylpyridines, 2-alkenylpyridine, and aromatic imines can be coupled with aryl bromides in the presence of an iron catalyst, metallic magnesium, a diamine ligand and an organic dihalide oxidant at 0 °C. The use of a 1:1 mixture of tetrahydrofuran and 1,4-dioxane is essential for this C[BOND]H bond activation reaction. The reaction has wider scope of the substrate compared with the reaction using a separately prepared Grignard reagent, and proceeds with lower catalyst loading (2.5 mol%).

Ancillary