Palladium-Catalyzed Cyclization: Regioselectivity and Structure of Arene-Fused C Derivatives.

The palladium-catalyzed cyclization on the fullerene C cage has been achieved using several aryl halides and C. This reaction was found to be accelerated by the addition of pivalic acid, which can be rationally explained by the computational study based on the concerted metalation-deprotonation mech...

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Publicado en:Journal of the American Chemical Society Vol. 139; no. 45; pp. 16350 - 16359
Autores principales: Yoshifumi Hashikawa, Atsushi Wakamiya, Yasujiro Murata
Formato: Artículo
Publicado: American Chemical Society 11/15/2017
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Acceso en línea:Ver este registro en EBSCOhost
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      dt: 11/15/2017
      vid: 139
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      pub: American Chemical Society
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        10.1021/jacs.7b09459
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        atl: Palladium-Catalyzed Cyclization: Regioselectivity and Structure of Arene-Fused C Derivatives.
      aug:
        au:
          Yoshifumi Hashikawa
          Atsushi Wakamiya
          Yasujiro Murata
        affil: Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan
      su:
        Palladium
        Ring formation (Chemistry)
        Nuclear magnetic resonance
        Density functional theory
        Hydrogen bonding
      sug:
        subj:
          Palladium
          Ring formation (Chemistry)
          Nuclear magnetic resonance
          Density functional theory
          Hydrogen bonding
      ab: The palladium-catalyzed cyclization on the fullerene C cage has been achieved using several aryl halides and C. This reaction was found to be accelerated by the addition of pivalic acid, which can be rationally explained by the computational study based on the concerted metalation-deprotonation mechanism. We also demonstrated the regioselective π-functionalization using prefunctionalized designed molecules possessing the same substructure on the C cage. The single crystal X-ray analysis and electrostatic potential map revealed that the orientation of entrapped HO inside the naphthalene-fused open-cage C derivative is electrostatically demanded due to the naphthalene-fusion and construction of the opening.
      pubtype: Academic Journal
      doctype: Article
      src: R
    language: English
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