Regioselectively Electrochemical Synthesis of N2-Selective C-H Amination of Ethers with N-Tosyl 1,2,3-Triazole via Triazole Radical Cation

Cong Guan; Jiabin Yin; Jian Ji; Jinhua Liu; Xiang Wu; Tong Zhu; Shunying Liu

doi:10.1021/acs.orglett.3c01896

Regioselectively Electrochemical Synthesis of N²-Selective C-H Amination of Ethers with N-Tosyl 1,2,3-Triazole via Triazole Radical Cation

Org Lett. 2023 Jul 21;25(28):5383-5388. doi: 10.1021/acs.orglett.3c01896. Epub 2023 Jul 7.

Authors

Cong Guan¹, Jiabin Yin¹, Jian Ji¹, Jinhua Liu¹, Xiang Wu¹, Tong Zhu¹, Shunying Liu¹

Affiliation

¹ Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.

PMID: 37418313
DOI: 10.1021/acs.orglett.3c01896

Abstract

A regioselective electrochemical C-H amination method to synthesize N²-substituted 1,2,3-triazole using easily accessible ethers has been developed. Various substituents, including heterocycles, have a good tolerance, and 24 examples were obtained in moderate to good yields. Control experiments and DFT calculation investigations demonstrate that the electrochemical synthesis undergoes a N-tosyl 1,2,3-triazole radical cation process promoted by the single-electron transfer of the lone pair electrons of the aromatic N-heterocycle, and the desulfonation is responsible for the high N²-regioselectivity.