Difluorocarbene-derived rapid late-stage trifluoromethylation of 5-iodotriazoles for the synthesis of 18F-labeled radiotracers
Difluorocarbene-derived rapid late-stage trifluoromethylation of 5-iodotriazoles for the synthesis of 18F-labeled radiotracers
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二氟卡宾衍生的 5-碘三唑的快速后期三氟甲基化用于合成 18F 标记的放射性示踪剂
DOI：
10.1016/j.cclet.2022.107960
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发表时间：
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影响因子：
9.1
通讯作者：
Haoxing Wu
中科院分区：
文献类型：
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作者：
Fang Yuan;Hongbao Sun;Cheng Yang;Haojie Yang;Lili Pan;Xiaoyang Zhang;Rong Tian;Lingjun Li;Wei Chen;Xiaoai Wu;Haoxing Wu
二氟卡宾是合成氟化物的重要中间体。然而，二氟卡宾衍生的19 F/18F-三氟甲基三唑的合成尚未被探索。本文报道了以KF/K18 F为氟源，Cu（I）促进的碘代三唑衍生的19 F/18F-三氟甲基化反应。该方法以良好的产率快速生成宽范围的5-三氟甲基-1，2，3-三唑，显示出高的官能团相容性。该反应对于生物活性分子的后期功能化和碘三唑的18F-三氟甲基化是有效的。本工作为三唑类药物和正电子发射断层显像用18F-放射性示踪剂的开发提供了一种实用的合成方法。
Difluorocarbene has emerged as a valuable intermediate to synthesize fluorides. However, difluorocarbene-derived synthesis of19F/18F-trifluoromethyl triazoles has not been explored. Herein, we reported the Cu(I)-promoted difluorocarbene-derived19F/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 and18F-trifluoromethylation of iodotriazoles. This work provides a practical synthetic methodology for the development of triazole drugs and18F-radiotracers for positron emission tomography.