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

作     者：Fang Yuan Hongbao Sun Cheng Yang Haojie Yang Lili Pan Xiaoyang Zhang Rong Tian Lingjun Li Wei Chen Xiaoai Wu Haoxing Wu Fang Yuan;Hongbao Sun;Cheng Yang;Haojie Yang;Lili Pan;Xiaoyang Zhang;Rong Tian;Lingjun Li;Wei Chen;Xiaoai Wu;Haoxing Wu

作者机构：Huaxi MR Research CenterDepartment of RadiologyFunctional and Molecular Imaging Key Laboratory of Sichuan ProvinceFrontiers Science Center for Disease-Related Molecular NetworkWest China HospitalSichuan UniversityChengdu 610041China Department of Nuclear MedicineLaboratory of Clinical Nuclear MedicineWest China HospitalSichuan UniversityChengdu 610041China School of Chemistry and Chemical EngineeringCollaborative Innovation Center of Henan Province for Green Manufacturing of Fine ChemicalsState Key Laboratory of Cell Differentiation Regulation and Target DrugHenan Normal UniversityXinxiang 453007China 

出 版 物：《Chinese Chemical Letters》 (中国化学快报（英文版）)

年 卷 期：2023年第34卷第6期

页      面：336-340页

核心收录：

学科分类：1007[医学-药学(可授医学、理学学位)] 0703[理学-化学] 10[医学] 

基　　金：financially supported by the National Natural Science Foundation of China(Nos.21977075,22271200,21801178,21907070,81971653) 1.3.5 Project for Disciplines of Excellence,West China Hospital,Sichuan University,Central Plains Science and Technology Innovation Leader Project(No.214200510008 to L.Li) Scientific and Technological Innovation Team of Colleges and Universities in Henan Province(No.21IRTSTHN001)。 

主　　题：Difluorocarbene Trifluoromethylation Triazole Late-stage functionalization ^(18)F-Labeled radiotracer 

摘      要：Difluorocarbene has emerged as a valuable intermediate to synthesize fluorides.However,difluorocarbene-derived synthesis of^(19)F/^(18)F-trifluoromethyl triazoles has not been explored.Herein,we reported the Cu(I)-promoted difluorocarbene-derived^(19)F/^(18)F-trifluoromethylation of iodotriazoles using KF/K^(18)F 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^(18)F-trifluoromethylation of iodotriazoles.This work provides a practical synthetic methodology for the development of triazole drugs and^(18)F-radiotracers for positron emission tomography.