Electrochemical Tandem Fluoroalkylation-Cyclization of Vinyl Azides: Access to Trifluoroethylated and Difluoroethylated N-Heterocycles. 2020

Long Lin, and Qi Liang, and Xianqiang Kong, and Qianjin Chen, and Bo Xu
Key Lab of Science and Technology of Eco-Textile, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China.

A transition-metal- and oxidant-free electrochemical strategy for radical fluoroalkylation of vinyl azides was developed. The reaction was carried out under mild conditions by using inexpensive and bench-stable RfSO2Na (Rf = CF3, CF2H) as fluorination reagents. Depending on the starting material, both the electrochemical radical cyclization and dearomatization products could be obtained. This method provides a green and safe approach to synthesize fluorinated nitrogen heterocycles.

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