Electrochemically Driven Ugi-Azide Reaction via C(sp<sup>3</sup>)–H Bond Activation of Tertiary Amines
Bin Song, Feng Zhao, Pengxiang Gao, Ruizong Wang, Xue‐Hai Ju, Bingcheng Hu, Chong Zhang
Abstract
)-H bond activation of tertiary amines to prepare α-aminomethyl tetrazoles within 2.5 h under mild conditions with remarkable tolerance of various functional groups. Besides, this electrochemical strategy not only obviated the needs of iodine, metal, and exogenous oxidant but possessed potential applicability of convenient large-scale synthesis. Mechanistic studies indicated both the alkyl carbon-centered radical generated at the anode and intramolecular [3 + 2] cycloaddition are key factors for this strategy.
Topics & Concepts
ChemistryCycloadditionIntramolecular forceAzideElectrochemistryAlkylMedicinal chemistryCombinatorial chemistryPhotochemistryOrganic chemistryCatalysisElectrodePhysical chemistryMulticomponent Synthesis of HeterocyclesSynthesis of Tetrazole DerivativesClick Chemistry and Applications