Synthesis of planar-chiral bridged bipyridines and terpyridines by metal-mediated coupling reactions of pyridinophanes

Nobuhiro Kanomata, Jun Suzuki, Hironobu Kubota, Kiichiro Nishimura, Terumichi Enomoto

    Research output: Contribution to journalArticle

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    Abstract

    We have accomplished efficient synthesis of planar-chiral bridged 2,2′-bipyridine (S)-6, C2-symmetric bipyridinophane (S,S)-7, bridged 2,2′:6′,2″-terpyridines (S)-11, and C2-symmetric terpyridine (S,S)-12 by metal-mediated biaryl cross-coupling or homo-coupling reactions of the corresponding 6-halo[10](2,5)pyridinophanes. Stille-type and Negishi cross-coupling reactions are particularly useful for the syntheses of 6, 11, and 12. On the other hand, nickel-mediated homo-coupling reaction worked best for achieving the synthesis of structurally unique bipyridinophane 7.

    Original languageEnglish
    Pages (from-to)2740-2743
    Number of pages4
    JournalTetrahedron Letters
    Volume50
    Issue number23
    DOIs
    Publication statusPublished - 2009 Jun 10

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    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

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    Synthesis of planar-chiral bridged bipyridines and terpyridines by metal-mediated coupling reactions of pyridinophanes. / Kanomata, Nobuhiro; Suzuki, Jun; Kubota, Hironobu; Nishimura, Kiichiro; Enomoto, Terumichi.

    In: Tetrahedron Letters, Vol. 50, No. 23, 10.06.2009, p. 2740-2743.

    Research output: Contribution to journalArticle

    Kanomata, Nobuhiro ; Suzuki, Jun ; Kubota, Hironobu ; Nishimura, Kiichiro ; Enomoto, Terumichi. / Synthesis of planar-chiral bridged bipyridines and terpyridines by metal-mediated coupling reactions of pyridinophanes. In: Tetrahedron Letters. 2009 ; Vol. 50, No. 23. pp. 2740-2743.
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    AU - Suzuki, Jun

    AU - Kubota, Hironobu

    AU - Nishimura, Kiichiro

    AU - Enomoto, Terumichi

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