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Indium(III)-Catalyzed Cationic Cyclization of 1,1-Difluoroallenes: Regioselective Synthesis of 1-Fluoronaphthalenes

  • Fuchibe Kohei
    Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba
  • Mayumi Yuka
    Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba
  • Yokota Misaki
    Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba
  • Aihara Hiromichi
    Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba
  • Ichikawa Junji
    Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba

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  • BCSJ Award Article : Indium(Ⅲ)-Catalyzed Cationic Cyclization of 1,1-Difluoroallenes : Regioselective Synthesis of 1-Fluoronaphthalenes

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Abstract

1,1-Difluoroallenes underwent InBr3-catalyzed ring construction via in situ-generated allylic CF2 cations to give 1-fluoronaphthalenes in good yield. DFT calculations suggested that a positive charge was localized on the CF2 carbon in the key allylic CF2 cation, which was stabilized by (1) α-cation stabilizing effect of the fluorines and (2) hyperconjugation with the adjuscent C–In σ bond.

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