Citation: Shoudong Xie, Weinan Chen, Si Liu, Hao Zong, Binbin Ming, Gang Zhou. Facile synthesis and functionalization of fluoranthenes via intramolecular [4 + 2] annulations between thiophenes and alkynes[J]. Chinese Chemical Letters, ;2023, 34(6): 107642. doi: 10.1016/j.cclet.2022.06.065 shu

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

Lab of Advanced Materials, State Key Laboratory of Molecular Engineering of Polymers, Fudan University, Shanghai 200438, China

zhougang@fudan.edu.cn

Received Date: 22 March 2022
Revised Date: 5 May 2022
Accepted Date: 23 June 2022
Available Online: 30 June 2022

Figures(3)

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.
- Fluoranthene,
- Annulation,
- Polycyclic aromatic hydrocarbon,
- Catalyst-free,
- S-extrusion
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