Synthesis of Pinpoint-Fluorinated Polycyclic Aromatic Hydrocarbons: Benzene Ring Extension Cycle Involving Microwave-Assisted SNAr Reaction

Fluoroarenes bearingnoelectron-withdrawing groups (non-activated fluoroarenes) readily underwent nu-cleophilic aromatic substitution with a-cyanocarbanions under microwave irradiation. The sequence (i)formylalkyla-tion involving the cyanoalkylation of fluoroarenes, (ii)di-fluorovinylidenati on, and (iii)Friedel–Crafts-typecycliza-tion, afforded extended fluoroarenes by one benzene ring per cycle. Furthermore, the performance of multiple cyclessuccessfully providedhigher-order pinpoint-fluorinated polycyclic aromatic hydrocarbons (F-PAHs)