Facile synthesis and functionalization of fluoranthenes via intramolecular[4+2]annulations between thiophenes and alkynes  

作　　者：Shoudong Xie Weinan Chen Si Liu Hao Zong Binbin Ming Gang Zhou 

机构地区：[1]Lab of Advanced Materials,State Key Laboratory of Molecular Engineering of Polymers,Fudan University,Shanghai 200438,China

出　　处：《Chinese Chemical Letters》2023年第6期476-479,共4页中国化学快报（英文版）

基　　金：financially supported by National Key Research and Development Program of China(No.2018YFA0209401);National Natural Science Foundation of China(Nos.22171053,21733003);Natural Science Foundation of Shanghai(No.21ZR1409600)。

摘　　要：Fluoranthenes have attracted tremendous attention due to their unique optoelectronic properties and extensive applications.Although several synthetic methodologies have been developed for the preparation of fluoranthene derivatives,it is still unfavorable to functionalize the fluoranthene framework at different positions due to the relatively low selectivity and reactivity.Herein,a catalyst-free intramolecular[4+2]annulation between thiophenes and alkynes is developed towards the synthesis of fluoranthenes.Altogether 20 examples have been demonstrated using this method.Various functional groups can be precisely introduced into the fluoranthene skeleton at different positions by simply tuning the substituents on the thiophenes and alkynes.The conjugation of the fluoranthene can be facilely extended through different directions.Furthermore,the feasibility of this[4+2]annulation reaction is also investigated by density functional theory calculations.Therefore,this protocol provides not only a synthetic methodology towards fluoranthenes with substituents functionalized at different positions,but also an effective pathway to construct large polycyclic aromatic hydrocarbons containing fluoranthene moieties.

关 键 词：FLUORANTHENE ANNULATION Polycyclic aromatic hydrocarbon CATALYST-FREE S-extrusion 

分 类 号：O621.25[理学—有机化学]