Citation: Fang Yuan, Hongbao Sun, Cheng Yang, Haojie Yang, Lili Pan, Xiaoyang Zhang, Rong Tian, Lingjun Li, Wei Chen, Xiaoai Wu, Haoxing Wu. Difluorocarbene-derived rapid late-stage trifluoromethylation of 5-iodotriazoles for the synthesis of ¹⁸F-labeled radiotracers[J]. Chinese Chemical Letters, ;2023, 34(6): 107960. doi: 10.1016/j.cclet.2022.107960 shu

Difluorocarbene-derived rapid late-stage trifluoromethylation of 5-iodotriazoles for the synthesis of ¹⁸F-labeled radiotracers

Fang Yuan ^{a, 1} ,
Hongbao Sun ^{a, 1} ,
Cheng Yang ^a ,
Haojie Yang ^a ,
Lili Pan ^b ,
Xiaoyang Zhang ^a ,
Rong Tian ^b ,
Lingjun Li ^c ,
Wei Chen ^b ,
Xiaoai Wu ^{b, *,} ,
Haoxing Wu ^{a, *,}

a.
Huaxi MR Research Center, Department of Radiology, Functional and Molecular Imaging Key Laboratory of Sichuan Province, Frontiers Science Center for Disease-Related Molecular Network, West China Hospital, Sichuan University, Chengdu 610041, China
b.
Department of Nuclear Medicine, Laboratory of Clinical Nuclear Medicine, West China Hospital, Sichuan University, Chengdu 610041, China
c.
School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, State Key Laboratory of Cell Differentiation Regulation and Target Drug, Henan Normal University, Xinxiang 453007, China

xiaoai.wu@scu.edu.cn

haoxingwu@scu.edu.cn

Received Date: 7 September 2022
Revised Date: 22 October 2022
Accepted Date: 26 October 2022
Available Online: 29 October 2022

Figures(4)

Difluorocarbene has emerged as a valuable intermediate to synthesize fluorides. However, difluorocarbene-derived synthesis of ¹⁹F/¹⁸F-trifluoromethyl triazoles has not been explored. Herein, we reported the Cu(I)-promoted difluorocarbene-derived ¹⁹F/¹⁸F-trifluoromethylation of iodotriazoles using KF/K¹⁸F as the fluorine source. This approach rapidly generated a wide range of 5-trifluoromethyl-1, 2, 3-triazoles in good yields showing high functional group compatibility. The reaction was effective for late-stage functionalization of bioactive molecules and ¹⁸F-trifluoromethylation of iodotriazoles. This work provides a practical synthetic methodology for the development of triazole drugs and ¹⁸F-radiotracers for positron emission tomography.
- Difluorocarbene,
- Trifluoromethylation,
- Triazole,
- Late-stage functionalization,
- ¹⁸F-Labeled radiotracer
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Difluorocarbene-derived rapid late-stage trifluoromethylation of 5-iodotriazoles for the synthesis of 18F-labeled radiotracers

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Difluorocarbene-derived rapid late-stage trifluoromethylation of 5-iodotriazoles for the synthesis of ¹⁸F-labeled radiotracers