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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.

Takeshi FujitaMarina TakazawaKazuki SugiyamaNaoto SuzukiJunji Ichikawa
Published in: Organic letters (2017)
The construction of ring-fluorinated seven-membered carbocycles was readily achieved via the domino SN2'-type/SNV reaction between 2-(trifluoromethyl)-1-alkenes and 1,4-carbodianions. The SN2'-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 SNV reaction to afford fluorinated 5H-dibenzo[a,c][7]annulenes.
Keyphrases
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