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

Long Lin; Qi Liang; Xianqiang Kong; Qianjin Chen; Bo Xu

doi:10.1021/acs.joc.0c02213

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

J Org Chem. 2020 Dec 4;85(23):15708-15716. doi: 10.1021/acs.joc.0c02213. Epub 2020 Nov 23.

Authors

Long Lin¹, Qi Liang¹, Xianqiang Kong^{1

2}, Qianjin Chen¹, Bo Xu¹

Affiliations

¹ Key Lab of Science and Technology of Eco-Textile, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China.
² School of Chemical Engineering and Materials, Changzhou Institute of Technology, No. 666 Liaohe Road, Changzhou 213032, China.

PMID: 33226809
DOI: 10.1021/acs.joc.0c02213

Abstract

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 R_fSO₂Na (R_f = 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.

Publication types

Research Support, Non-U.S. Gov't