Visible-Light-Promoted Transition-Metal-Free Construction of 3-Perfluoroalkylated Thioflavones

Chunhua Ma; Hui Meng; Xing He; Yuqin Jiang; Bing Yu

doi:10.3389/fchem.2022.953978

Visible-Light-Promoted Transition-Metal-Free Construction of 3-Perfluoroalkylated Thioflavones

Front Chem. 2022 Jul 13:10:953978. doi: 10.3389/fchem.2022.953978. eCollection 2022.

Authors

Chunhua Ma¹, Hui Meng¹, Xing He¹, Yuqin Jiang¹, Bing Yu²

Affiliations

¹ Collaborative Innovation Centre of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Engineering Research Centre of Chiral Hydroxyl Pharmaceutical, Henan Engineering Laboratory of Chemical Pharmaceutical and Biomedical Materials, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, China.
² Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou, China.

Abstract

A visible-light-promoted transition-metal-free perfluoroalkylation/cyclization reaction was developed with 9-mesityl-10-methylacridinium perchlorate (Acr⁺-Mes·ClO₄ ^-) as the photocatalyst, by which various perfluoroalkyl-substituted heterocycles including thioflavones, oxindoles, and quinoline-2,4(1H,3H)-diones were prepared at room temperature. Moreover, the potential of this sustainable method is demonstrated by the excellent in vitro anti-lymphoma and cervical carcinoma activity of the novel 3-perfluoroalkylated thioflavone 3m.

Keywords: antitumor; cyclization; perfluoroalkylation; photocatalysis; thioflavone.