Synthesis of aryl-platinum dinuclear complexes via ortho C-H bond activation of phenol and transmetalation of arylboronic acid

Masahiko Ochiai, Kôichi Fukui, Satoshi Iwatsuki, Koji Ishihara, Kazuko Matsumoto

    Research output: Contribution to journalArticle

    27 Citations (Scopus)

    Abstract

    The reaction of the pivalamidate-bridged platinum(III) dinuclear complex [Pt2(NH3)4(tBuCONH) 2(OH2)2]4+ with phenol in water gave 2-hydroxyphenyl platinum dinuclear complex [Pt2(NH3) 4(tBuCONH)2(C6H4(OH))] 3+ via ortho C-H bond activation in the axial position. The identical compound and the analogous phenyl complex [Pt2(NH3) 4(tBuCONH)2(C6H5)] 3+ could alternatively be synthesized from the reactions of [Pt 2(NH3)4(tBuCONH)2(OH 2)2]4+ with the corresponding arylboronic acids via transmetalation. The reactivities of the novel aryl-Pt2 compounds toward nucleophiles and the effect of UV light irradiation were investigated. The ESR spectra showed that the axial aryl-Pt bond is homolytically cleaved by UV-light irradiation to give the aryl radical and the Pt(III)-Pt(II) paramagnetic complex.

    Original languageEnglish
    Pages (from-to)5528-5536
    Number of pages9
    JournalOrganometallics
    Volume24
    Issue number23
    DOIs
    Publication statusPublished - 2005 Nov 7

    Fingerprint

    Phenol
    Platinum
    Ultraviolet radiation
    phenols
    platinum
    Chemical activation
    Irradiation
    activation
    Nucleophiles
    acids
    irradiation
    Acids
    aromatic compounds
    nucleophiles
    synthesis
    Paramagnetic resonance
    reactivity
    Water
    water

    ASJC Scopus subject areas

    • Inorganic Chemistry
    • Organic Chemistry

    Cite this

    Synthesis of aryl-platinum dinuclear complexes via ortho C-H bond activation of phenol and transmetalation of arylboronic acid. / Ochiai, Masahiko; Fukui, Kôichi; Iwatsuki, Satoshi; Ishihara, Koji; Matsumoto, Kazuko.

    In: Organometallics, Vol. 24, No. 23, 07.11.2005, p. 5528-5536.

    Research output: Contribution to journalArticle

    Ochiai, Masahiko ; Fukui, Kôichi ; Iwatsuki, Satoshi ; Ishihara, Koji ; Matsumoto, Kazuko. / Synthesis of aryl-platinum dinuclear complexes via ortho C-H bond activation of phenol and transmetalation of arylboronic acid. In: Organometallics. 2005 ; Vol. 24, No. 23. pp. 5528-5536.
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    AU - Fukui, Kôichi

    AU - Iwatsuki, Satoshi

    AU - Ishihara, Koji

    AU - Matsumoto, Kazuko

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    AB - The reaction of the pivalamidate-bridged platinum(III) dinuclear complex [Pt2(NH3)4(tBuCONH) 2(OH2)2]4+ with phenol in water gave 2-hydroxyphenyl platinum dinuclear complex [Pt2(NH3) 4(tBuCONH)2(C6H4(OH))] 3+ via ortho C-H bond activation in the axial position. The identical compound and the analogous phenyl complex [Pt2(NH3) 4(tBuCONH)2(C6H5)] 3+ could alternatively be synthesized from the reactions of [Pt 2(NH3)4(tBuCONH)2(OH 2)2]4+ with the corresponding arylboronic acids via transmetalation. The reactivities of the novel aryl-Pt2 compounds toward nucleophiles and the effect of UV light irradiation were investigated. The ESR spectra showed that the axial aryl-Pt bond is homolytically cleaved by UV-light irradiation to give the aryl radical and the Pt(III)-Pt(II) paramagnetic complex.

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