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Synthesis of Pinpoint-Fluorinated Polycyclic Aromatic Hydrocarbons: Benzene Ring Extension Cycle Involving Microwave-Assisted S N Ar Reaction.
Chemistry, An Asian Journal 2017 September 20
Fluoroarenes bearing no electron-withdrawing groups (non-activated fluoroarenes) readily underwent nucleophilic aromatic substitution with α-cyanocarbanions under microwave irradiation. The sequence (i) formylalkylation involving the cyanoalkylation of fluoroarenes, (ii) difluorovinylidenation, and (iii) Friedel-Crafts-type cyclization, afforded extended fluoroarenes by one benzene ring per cycle. Furthermore, the performance of multiple cycles successfully provided higher-order pinpoint-fluorinated polycyclic aromatic hydrocarbons (F-PAHs).
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