Indium(III)-Catalyzed Cationic Cyclization of 1,1-Difluoroallenes: Regioselective Synthesis of 1-Fluoronaphthalenes
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- Fuchibe Kohei
- Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba
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- Mayumi Yuka
- Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba
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- Yokota Misaki
- Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba
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- Aihara Hiromichi
- Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba
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- Ichikawa Junji
- Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba
Bibliographic Information
- Other Title
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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.
Journal
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 87 (9), 942-949, 2014
The Chemical Society of Japan
