Citation: Gou Baoquan, Yang Chao, Zhang Lei, Xia Wujiong. Visible-Light Induced Trifluoromethylation of Internal Olefinic C-H Bonds through Photoredox Catalysis[J]. Acta Chimica Sinica, ;2017, 75(1): 66-69. doi: 10.6023/A16070341 shu

Visible-Light Induced Trifluoromethylation of Internal Olefinic C-H Bonds through Photoredox Catalysis

School of Chemistry and Chemical Engineering, State Key Lab of Urban Water Resource and Environment, Harbin Institute of Technology, Harbin 150080

Corresponding author: Yang Chao, xyyang@hit.edu.cn Xia Wujiong, xiawj@hit.edu.cn
Received Date: 15 July 2016

Fund Project: State Key Laboratory of Urban Water Resource and Environment 2015DX01National Natural Science Foundation of China 21472030National Natural Science Foundation of China 21372055National Natural Science Foundation of China 21272047and the Fundamental Research Funds for the Central Universities HIT.BRETIV.201310

Figures(4)

An approach for direct trifluoromethylation of internal olefins of α-oxoketene dithioacetals has been achieved by using Ru (bpy)₃Cl₂ as photocatalyst and Togni's reagent as trifluoromethylating agent under irradiation with visible light. Under a nitrogen atmosphere, a mixture of α-oxoketene dithioacetal (0.1 mmol), Togni's reagent (0.15 mmol), Ru (bpy)₃Cl₂ (0.005 mmol), and Na₂CO₃ (0.3 mmol) in DMSO (1 mL) was stirred at room temperature for 72 h under 5 W Blue LEDS, which led to the trifluoromethylated products in 40%~90% yield. This protocol provides an efficient and easy access to prepare trifluoromethylated dithioalkyl α-oxoketene acetals under mild conditions, and is highlighted by its operational simplicity and avoiding using toxic reagent. Furthermore, the gram-scale reaction of 1a suggested the potential application of this protocol in organic synthesis.
- visible light,
- olefin,
- trifluoromethylation,
- photocatalyst,
- operational simplicity
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