Regioselectively Electrochemical Synthesis of N 2-Selective C-H Amination of Ethers with N-Tosyl 1,2,3-Triazole via Triazole Radical Cation

Authors：Guan, Cong; Yin, Jiabin; Ji, Jian; Liu, Jinhua; Wu, Xiang; Zhu, Tong^*; Liu, Shunying^*

Source：Organic Letters, 2023, 25(28): 5383-5388.

DOI：10.1021/acs.orglett.3c01896

• CLICK CHEMISTRY
• CYCLOADDITION
• ALKYNES
• AZIDE

A regioselective electrochemical C-H aminationmethod tosynthesize N (2)-substituted 1,2,3-triazoleusing easily accessible ethers has been developed. Various substituents,including heterocycles, have a good tolerance, and 24 examples wereobtained in moderate to good yields. Control experiments and DFT calculationinvestigations demonstrate that the electrochemical synthesis undergoesa N-tosyl 1,2,3-triazole radical cation process promotedby the single-electron transfer of the lone pair electrons of thearomatic N-heterocycle, and the desulfonation isresponsible for the high N (2)-regioselectivity.