Visible-Light Induced Trifluoromethylation of Internal Olefinic C-H Bonds through Photoredox Catalysis
Received date: 2016-07-15
Revised date: 2016-08-17
Online published: 2016-08-24
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21272047, 21372055 and 21472030), State Key Laboratory of Urban Water Resource and Environment (No. 2015DX01) and the Fundamental Research Funds for the Central Universities (No. HIT.BRETIV.201310).
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.
Key words： visible light; olefin; trifluoromethylation; photocatalyst; operational simplicity
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
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