Regioselectively Electrochemical Synthesis of <i>N</i><sup>2</sup>-Selective C–H Amination of Ethers with <i>N</i>-Tosyl 1,2,3-Triazole via Triazole Radical Cation
Cong Guan, Jiabin Yin, Jian Ji, Jinhua Liu, Xiang Wu, Tong Zhu, Shunying Liu
Abstract
A regioselective electrochemical C–H amination method to synthesize N 2 -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 N 2 -regioselectivity.
Topics & Concepts
ChemistryRegioselectivityAminationTosylElectrochemistryLone pairTriazole1,2,4-TriazoleMedicinal chemistryCombinatorial chemistryElectron transferOrganic chemistryMoleculeCatalysisPhysical chemistryElectrodeCO2 Reduction Techniques and CatalystsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques