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 monodeuterodefluorinat...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.展开更多
基金supported by the National Science Foundation of China(grant nos.22071105 and 22031008)the QingLan Project of Jiangsu Education Department.
文摘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.
