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Amination of meso-Bromoporphyrins and 9-Haloanthracenes with Diarylamines Catalyzed by a Palladium–PEPPSI Complex

Authors

  • Yuko Suzuki,

    1. Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-3970
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  • Norihito Fukui,

    1. Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-3970
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  • Dr. Kei Murakami,

    1. Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-3970
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  • Prof. Dr. Hideki Yorimitsu,

    Corresponding author
    1. Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-3970
    2. ACT-C, Japan Science and Technology Agency
    • Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-3970

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  • Prof. Dr. Atsuhiro Osuka

    Corresponding author
    1. Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-3970
    • Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-3970

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Abstract

Palladium-catalyzed aminations of bulky aryl halides such as meso-bromoporphyrins and 9-haloanthracenes with diarylamines provided efficient syntheses of meso-aminoporphyrins and 9-aminoanthracenes. Commercially available and air-stable Pd-PEPPSI complexes that have N-heterocyclic carbene (NHC) as ligands have the highest catalytic activities. The scope of diarylamines is wide enough to use diphenylamine, phenoxazine, phenothiazine, 9,10-dihydroacrydine, and carbazole.

Abstract

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