Unusual ipso Substitution of Diaryliodonium Bromides Initiated by a Single-Electron-Transfer Oxidizing Process

Authors

  • Toshifumi Dohi Dr.,

    1. College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577 (Japan), Fax: (+81) 77-561-5829
    2. Graduate School of Pharmaceutical Sciences, Osaka University, 1–6 Yamada-oka, Suita, Osaka 565-0871 (Japan)
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  • Motoki Ito,

    1. Graduate School of Pharmaceutical Sciences, Osaka University, 1–6 Yamada-oka, Suita, Osaka 565-0871 (Japan)
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  • Nobutaka Yamaoka,

    1. College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577 (Japan), Fax: (+81) 77-561-5829
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  • Koji Morimoto Dr.,

    1. College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577 (Japan), Fax: (+81) 77-561-5829
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  • Hiromichi Fujioka Prof. Dr.,

    1. Graduate School of Pharmaceutical Sciences, Osaka University, 1–6 Yamada-oka, Suita, Osaka 565-0871 (Japan)
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  • Yasuyuki Kita Prof. Dr.

    1. College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577 (Japan), Fax: (+81) 77-561-5829
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  • This work was supported by Grants-in-Aid for Scientific Research (A) from the Japan Society for the Promotion of Science (JSPS), Grants-in-Aid for Young Scientists (B) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), and the Ritsumeikan Global Innovation Research Organization (R-GIRO) project. T.D. acknowledges support from the Industrial Technology Research Grant Program from the New Energy and Industrial Technology Development Organization (NEDO) of Japan. M.I. acknowledges a Research Fellowship for Young Scientists from JSPS.

Abstract

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Iod kuppelt: Die Umsetzung der Diaryliodoniumbromide 1 mit aromatischen Nucleophilen 2 ergab eine Reihe von Heterobiarylen 3 in guten Ausbeuten. Diese ipso-Substitution am Heteroarenring von 1 verläuft über aromatische Radikalkationen, die durch Einelektronentransfer(SET)-Oxidation von 2 erzeugt werden. HFIP=Hexafluor-2-propanol.

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