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Substituent Effect of Bis(pyridines)iodonium Complexes as Iodinating Reagents: Control of the Iodocyclization/Oxidation Process

Authors

  • Dr. Takashi Okitsu,

    1. Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, 4-19-1, Motoyamakita-machi, Higashinada-ku, Kobe 658-8558 (Japan), Fax: (+81) 78-441-7562
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  • Saki Yumitate,

    1. Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, 4-19-1, Motoyamakita-machi, Higashinada-ku, Kobe 658-8558 (Japan), Fax: (+81) 78-441-7562
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  • Kana Sato,

    1. Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, 4-19-1, Motoyamakita-machi, Higashinada-ku, Kobe 658-8558 (Japan), Fax: (+81) 78-441-7562
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  • Dr. Yasuko In,

    1. Department of Physical Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1, Nasahara, Takatsuki, Osaka 569-1094 (Japan)
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  • Prof. Dr. Akimori Wada

    Corresponding author
    1. Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, 4-19-1, Motoyamakita-machi, Higashinada-ku, Kobe 658-8558 (Japan), Fax: (+81) 78-441-7562
    • Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, 4-19-1, Motoyamakita-machi, Higashinada-ku, Kobe 658-8558 (Japan), Fax: (+81) 78-441-7562
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Abstract

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Halogen bond: The choice of the iodonium complex of pyridines, either IPy2PF6 or I(coll)2PF6 (Py=pyridine; coll=2,4,6-trimethylpyridine), was crucial for controlling the iodocyclization/oxidation sequence of α-propargylic glycine derivatives. This reagent-controlled system enabled switchable access to 2,3-dihydropyrroles and pyrroles (see scheme).

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