Electrochemical Mono-Deuterodefluorination of Trifluoromethyl Aromatic Compounds with Deuterium Oxide  

作　　者：Jie Sheng Xu Cheng 

机构地区：[1]Institute of Chemistry and Biomedical Sciences,Jiangsu Key Laboratory of Advanced Organic Materials,School of Chemistry and Chemical Engineering,Nanjing University,Nanjing 210023 [2]State Key Laboratory of Elemento-Organic Chemistry,Nankai University,Tianjin 30071

出　　处：《CCS Chemistry》2024年第1期230-240,共11页中国化学会会刊（英文）

基　　金：supported by the National Science Foundation of China(grant nos.22071105 and 22031008);the QingLan Project of Jiangsu Education Department.

摘　　要：The deuterodifluoromethyl group CF_(2)D combines the structural features of CF_(3) and CD_(3) groups,finding wide applications in diverse pharmaceutical entities.In this work,the electrochemical monodeuterodefluorination of Ar-CF_(3) to Ar-CF_(2)D is achieved with an unreported deuterium atom transfer-coupled electron transfer pathway using D_(2)O as the only D source for the first time.A series of Ar-CF_(3) substances,including commercial pharmaceuticals,were converted to corresponding CF_(2)D products in up to 91% yield and 97% D-incorporation.A variety of functional groups,including pyridine,pyrrole,furan,thiophene,borate,thio ether,amine,amide,sulfonamide,and halide,are well tolerated in this protocol.t-BuOLi was an essential reagent to achieve chemoselective mono-defluorination.

关 键 词：ELECTROCHEMISTRY C-F activation fluorinecontaining drugs deuterated drugs deuterium oxide 

分 类 号：O62[理学—有机化学]