Domino C–F Bond Activation of the CF3 Group: Synthesis of Fluorinated Dibenzo[a,c][7]annulenes from 2-(Trifluoromethyl)-1-alkenes and 2,2′-Diceriobiaryls

Authors: Takeshi Fujita, Marina Takazawa, Kazuki Sugiyama, Naoto Suzuki, Junji Ichikawa - Organic Letters 2017 cited by 80

The construction of ring-fluorinated seven-membered carbocycles was readily achieved via the domino S N 2′-type/S N V reaction between 2-(trifluoromethyl)-1-alkenes and 1,4-carbodianions. The S N 2′-type reaction of 2-(trifluoromethyl)-1-alkenes with 2,2′-diceriobiaryls generated the intermediary 1,1-difluoro-1-alkenes bearing a monoceriobiaryl moiety, which in turn underwent intramolecular S N V reaction to afford fluorinated 5 H -dibenzo[ a, c ][7]annulenes.