Citation: Wanqiu Zhao, Aijia Zhang, Qingyun Huang, Pingping Tang. Selective meta-C-H trifluoromethylation of pyridines via 1,4-dihydropyridinephosphonate[J]. Chinese Chemical Letters, ;2026, 37(9): 112133. doi: 10.1016/j.cclet.2025.112133 shu

Selective meta-C-H trifluoromethylation of pyridines via 1,4-dihydropyridinephosphonate

State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China

huangqy@nankai.edu.cn

ptang@nankai.edu.cn

Received Date: 18 September 2025
Revised Date: 5 November 2025
Accepted Date: 17 November 2025
Available Online: 19 November 2025

Figures(3)

The meta-selective trifluoromethylation of pyridines has remained a significant challenge due to the inherent electronic constraints of the aromatic system. This study developed a novel dearomatization-rearomatization strategy based on 1,4-dihydropyridinephosphonate intermediates, which underwent copper-catalyzed regioselective C–CF₃ bond formation with Togni Ⅱ reagent followed by DABCO-promoted rearomatization, achieving highly regioselective meta-C-H trifluoromethylation of pyridine derivatives. This approach accommodated mostly meta-substituted pyridine substrates and enabled late-stage meta-C-H trifluoromethylation of pharmaceutical molecules containing pyridine motifs.
- meta-C-H trifluoromethylation,
- Dearomatization-rearomatization strategy,
- 1,4-Dihydropyridinephosphonate,
- Copper catalyst,
- Togni Ⅱ reagent
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