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Synthesis of Pinpoint‐Fluorinated Polycyclic Aromatic Hydrocarbons: Benzene Ring Extension Cycle Involving Microwave‐Assisted S N Ar Reaction
Author(s) -
Fuchibe Kohei,
Imaoka Hisanori,
Ichikawa Junji
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201700870
Subject(s) - benzene , ring (chemistry) , microwave , polycyclic aromatic hydrocarbon , chemistry , photochemistry , environmental chemistry , organic chemistry , computer science , telecommunications
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).