Synthesis of Pinpoint-Fluorinated Polycyclic Aromatic Hydrocarbons: Benzene Ring Extension Cycle Involving Microwave-Assisted SNAr Reaction
Synthesis of Pinpoint-Fluorinated Polycyclic Aromatic Hydrocarbons: Benzene Ring Extension Cycle Involving Microwave-Assisted SNAr Reaction
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DOI：
10.1002/asia.201700870
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发表时间：
2017-09-19
影响因子：
4.1
通讯作者：
Ichikawa, Junji
中科院分区：
文献类型：
--
作者：
Fuchibe, Kohei;Imaoka, Hisanori;Ichikawa, Junji
不含吸电子基团的氟代芳烃（非活化氟代芳烃）在微波辐射下容易发生亲核芳族取代与氰基碳负离子。顺序（i）涉及氟代芳烃的氰基烷基化的甲酰基烷基化，（ii）二氟乙烯基化，和（iii）Friedel-Crafts型环化，通过每个循环一个苯环提供扩展的氟代芳烃。此外，多次循环的性能成功地提供了更高阶的针尖氟化多环芳烃（F-PAH）。
Fluoroarenes bearing no electron-withdrawing groups (non-activated fluoroarenes) readily underwent nucleophilic aromatic substitution with -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).