Citation: Xuejiao Tang, Kun Liu, Zeming Qu, Junyan Zhan, Rukui Zhu, Fan Teng, Lili Meng, Yanmin Huang, Chusheng Huang, Yimiao He, Qiang Zhu. Convenient and efficient access to tri- and tetra-substituted 4-fluoropyridines via a [3 + 2]/[2 + 1] cyclization reaction[J]. Chinese Chemical Letters, ;2022, 33(6): 2982-2986. doi: 10.1016/j.cclet.2022.02.031 shu

Convenient and efficient access to tri- and tetra-substituted 4-fluoropyridines via a [3 + 2]/[2 + 1] cyclization reaction

Xuejiao Tang ^{a, 1} ,
Kun Liu ^{a, 1} ,
Zeming Qu ^a ,
Junyan Zhan ^a ,
Rukui Zhu ^a ,
Fan Teng ^c ,
Lili Meng ^a ,
Yanmin Huang ^a ,
Chusheng Huang ^a ,
Yimiao He ^{a, *,} ,
Qiang Zhu ^{a, b}

a.
Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, College of Chemistry and Materials, Nanning Normal University, Nanning 530001, China
b.
Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510530, China
c.
Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China

heyimiao@gxtc.edu.cn

Received Date: 13 December 2021
Revised Date: 10 February 2022
Accepted Date: 14 February 2022
Available Online: 18 February 2022

Figures(6)

A [3 + 2]/[2 + 1] cycloaddition reaction of gem-difluorocyclopropenes is presented, offering a mild and efficient approach to accessing tri- and tetra-substituted 4-fluoropyridines in moderate to good yields with excellent regioselectivity. Multiple synthetic applications, including process-scale reactions, modification of bioactive molecules, derivatization reactions and synthesis of the analogue of the PKM2 modulator, are subsequently described.
- 4-Fluoropyridine,
- gem-Difluorocyclopropene,
- [3 + 2]/[2 + 1] cyclization reaction,
- DMSO as an oxidant,
- Regioselectivity,
- PKM2 modulator
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