Citation: Xu Zheng, Zhou Bingwei, Jin Hongwei, Liu Yunkui. K₂S₂O₈/H₂O/NaOTf System-Promoted Schmidt Rearrangement Reaction of Vinyl Azides[J]. Chinese Journal of Organic Chemistry, ;2018, 38(7): 1823-1828. doi: 10.6023/cjoc201801025 shu

K₂S₂O₈/H₂O/NaOTf System-Promoted Schmidt Rearrangement Reaction of Vinyl Azides

State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Corresponding author: Liu Yunkui, ykuiliu@zjut.edu.cn
Received Date: 18 January 2018
Revised Date: 19 March 2018
Available Online: 4 July 2018
Fund Project: the National Natural Science Foundation of China 21772176the National Natural Science Foundation of China 21372201Project supported by the National Natural Science Foundation of China (Nos. 21772176, 21372201), the Opening Foundation of Zhejiang Key Course of Chemical Engineering and Technology, Zhejiang University of Technology

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Under neutral reaction conditions, sodium triflate promotes the radical reaction of potassium persulfate with water to yield a proton which induces Schmidt rearrangement of alkenyl azides. A variety of substituted acetanilide compounds were synthesized in one step. To obtain the optimal reaction conditions, an arrange of reaction parameters such as radical initiator, solvent, temperature, and reaction time have been screened. This reaction features an easy accessibility of starting materials, simple operation, broad substrate scope and so on. We finally proposed the plausible mechanism based on the mechanistic studies and previous literature.
- vinyl azides,
- acetanilides,
- radical reaction,
- Schmidt rearrangement
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K₂S₂O₈/H₂O/NaOTf System-Promoted Schmidt Rearrangement Reaction of Vinyl Azides