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

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

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...

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Veröffentlicht in:Bulletin of the Chemical Society of Japan 2014-09, Vol.87 (9), p.942-949
Hauptverfasser: Fuchibe, Kohei, Mayumi, Yuka, Yokota, Misaki, Aihara, Hiromichi, Ichikawa, Junji
Format: Artikel
Sprache:eng
Schlagworte:
Bonding
Carbon
Cationic
Cations
Charge
Construction
Mathematical analysis
Synthesis
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Zusammenfassung: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.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.20140128