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

Fuchibe, Kohei  ,  Imaoka, Hisanori  ,  Ichikawa, Junji

12 ( 18 )  , pp.2359 - 2363 , 2017-09 , Wiley-VCH
ISSN:18614728
NCID:AA12151701
Description
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).
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