Citation: Shi-Jing Zhai, Dominique Cahard, Fa-Guang Zhang, Jun-An Ma. Metal-free regioselective construction of 2-aryl-2H-tetrazol-5-yl difluoromethylene phosphonates[J]. Chinese Chemical Letters, ;2022, 33(2): 863-866. doi: 10.1016/j.cclet.2021.08.007 shu

Metal-free regioselective construction of 2-aryl-2H-tetrazol-5-yl difluoromethylene phosphonates

Shi-Jing Zhai ^{a, b} ,
Dominique Cahard ^c ,
Fa-Guang Zhang ^{a, b, *,} ,
Jun-An Ma ^{a, b, *,}

a.
Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Frontiers Science Center for Synthetic Biology (Ministry of Education), and Tianjin Collaborative Innovation Centre of Chemical Science & Engineering, Tianjin University, Tianjin 300072, China
b.
Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Fuzhou 350207, China
c.
CNRS UMR 6014 COBRA, Normandie Université, Mont Saint Aignan 76821, France

zhangfg1987@tju.edu.cn

majun_an68@tju.edu.cn

Received Date: 31 May 2021
Revised Date: 1 August 2021
Accepted Date: 2 August 2021
Available Online: 8 August 2021

Figures(6)

Three bench-stable difluoromethylene phosphonate hydrazones were prepared from simple diethyl(difluoromethyl)phosphonate within two steps in good yields. The [3 + 2] cycloaddition reaction of these diazo precursors with aryl diazonium salts has been accomplished under metal-free conditions with exclusive regioselectivity. This transformation provides practical access to a broad panel of 2-aryl-2H-tetrazol-5-yl difluoromethylene phosphonates, including the corresponding derivatives of amino acid (phenylalanine) and drug cores (Pomalidomide and Lapatinib fragment).
- Tetrazole,
- Cycloaddition,
- Difluoromethylene phosphonate,
- Regioselectivity,
- Diazonium salt
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