Get access
Advertisement

Copper-Mediated C[BOND]C Cross-Coupling Reaction of Monocarba-closo-dodecaborate Anion for the Synthesis of Functional Molecules

Authors

  • Junichiro Kanazawa,

    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    Search for more papers by this author
  • Prof. Dr. Ryo Takita,

    Corresponding author
    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    • Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    Search for more papers by this author
  • Dr. Aleksandra Jankowiak,

    1. Department of Chemistry, Vanderbilt University, Box 1822 Sta B, Nashville, TN 37235 (USA)
    2. Faculty of Chemistry, University of Łódź, 91403 Łódź (Poland)
    Search for more papers by this author
  • Prof. Dr. Shinya Fujii,

    1. Graduate School of Biomedical Science, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062 (Japan)
    Search for more papers by this author
  • Prof. Dr. Hiroyuki Kagechika,

    1. Graduate School of Biomedical Science, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062 (Japan)
    Search for more papers by this author
  • Prof. Dr. Daisuke Hashizume,

    1. Materials Characterization Support Unit, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198 (Japan)
    Search for more papers by this author
  • Prof. Dr. Koichi Shudo,

    1. Research Foundation ITSUU Laboratory, 2-28-10 Tamagawa, Setagaya-ku, Tokyo 158-0094 (Japan)
    Search for more papers by this author
  • Prof. Dr. Piotr Kaszyński,

    1. Department of Chemistry, Vanderbilt University, Box 1822 Sta B, Nashville, TN 37235 (USA)
    2. Faculty of Chemistry, University of Łódź, 91403 Łódź (Poland)
    Search for more papers by this author
  • Prof. Dr. Masanobu Uchiyama

    Corresponding author
    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    2. Elements Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198 (Japan)
    • Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    Search for more papers by this author

  • We thank Prof. Taniyuki Furuyama at Tohoku University for the valuable discussions, Prof. Motomu Kanai and Dr. Yuta Tanaka at the University of Tokyo for the ESI-MS measurements, and Ryoko Hirata at the University of Tokyo for the elemental analysis. This work was supported by JSPS KAKENHI (S) (No. 24229001) (to M.U.), Grant-in-Aid for Young Scientists (A) (No. 25713001) (to R.T.), National Science Foundation (DMR-1207585) (to P.K.). This research was also supported by Takeda Science Foundation, The Asahi Glass Foundation, Daiichi-Sankyo Foundation of Life Science, Mochida Memorial Foundation, Tokyo Biochemical Research Foundation, Foundation NAGASE Science Technology Development, and Sumitomo Foundation (to M.U.), and Astellas Foundation for Research on Metabolic Disorders (to R.T.).

Abstract

original image

Kreuzkupplungen am Kohlenstoff-Eckzentrum eines Monocarba-closo-dodecaborats ermöglichen die effiziente Einführung verschiedener Arylgruppen und anderer über sp2/sp-hybridisierte Kohlenstoffzentren gebundener Substituenten. Ein Kupfer(I)-Komplex erleichtert die Umsetzung mit zahlreichen Elektrophilen bei Raumtemperatur. Die Reaktion lieferte eine Reihe C-arylierter Carboran-Anionen (siehe Bild; B grün, C blau), darunter auch an Androgen-Rezeptoren bindende Substanzen und solche mit mesogenen Eigenschaften.

Get access to the full text of this article

Ancillary