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

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概要

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• 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.

• 公益社団法人 日本化学会の論文

著者

• FUCHIBE Kohei

  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

• ICHIKAWA Junji

  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

• Mayumi Yuka

  Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba

関連論文

• γ-Selective Addition to 1,1-Difluoroallenes : Three-component Coupling Leading to 2,2-Disubstituted 1,1-Difluoroalkenes
• Indium(III)-Catalyzed Cationic Cyclization of 1,1-Difluoroallenes: Regioselective Synthesis of 1-Fluoronaphthalenes
• Redox Switching of Conjugation Length Using 9,9,10,10-Tetraaryl-9,10-dihydrophenanthrene as an ON/OFF Unit : Preparation, X-ray Structure, and Redox Properties of Perfluorobiphenyl Derivative and Its SNAr Reactions to π-Extended Analogues

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