Citation: Lu Wang, Huaiyu Wang, Weidong Meng, Xiu-Hua Xu, Yangen Huang. Facile syntheses of 3-trifluoromethylthio substituted thioflavones and benzothiophenes via the radical cyclization[J]. Chinese Chemical Letters, ;2021, 32(1): 389-392. doi: 10.1016/j.cclet.2020.02.040 shu

Facile syntheses of 3-trifluoromethylthio substituted thioflavones and benzothiophenes via the radical cyclization

Lu Wang ^a ,
Huaiyu Wang ^a ,
Weidong Meng ^a ,
Xiu-Hua Xu ^b ,
Yangen Huang ^{a, *,}

a.
Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China
b.
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

hyg@dhu.edu.cn

Received Date: 19 January 2020
Revised Date: 6 February 2020
Accepted Date: 20 February 2020
Available Online: 20 February 2020

Figures(5)

3-CF₃S substituted thioflavones and benzothiophenes were achieved via the reactions of AgSCF₃ with methylthiolated alkynones and alkynylthioanisoles, respectively, promoted by persulfate. This protocol possesses good functional group tolerance and high yields. Mechanistic studies suggested that a classic two-step radical process was involved, which includes addition of CF₃S radical to triple bond and cyclization with SMe moiety.
- Trifluoromethylthiolation,
- Radical cyclization,
- Thioflavone,
- Benzothiophene,
- Methylthiolated alkynone,
- Alkynylthioanisole
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