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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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Aromatic substitution: The treatment of diaryliodonium bromides 1 with aromatic nucleophiles 2, afforded a variety of heteroaryl-containing biaryls 3 in good yields. The ipso-substitution process at the heteroaryl ring in 1 occurs through the formation of aromatic cation radicals, which are initiated by the single-electron-transfer (SET) oxidation of 2. (HFIP= hexafluoroisopropanol)

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