Chemistry - A European Journal · 2023 · 24 citations · 103 references
Natural SciencesChemistryMedicinal ChemistryCatalysisElectrochemistryOrganic ChemistryAmino Acid ChemistryCatalytic MechanismsCross-coupling ReactionsElectrochemical SynthesisHeterocycle SynthesisHeterocyclic ChemistryAmino Acid-derived HeterocyclesAmino AcidsChemo-selectivityCross-electrophile CouplingHeterocyclic Ring OpeningMild Reaction ConditionsSubstrate ScopeSubstrate Scope Expansion
Abstract Herein, a nickela‐electrocatalyzed cross‐electrophile coupling of readily available aryl aziridines and aryl bromides under mild and sustainable electrochemical conditions to access synthetic useful β ‐arylethylamines is developed. This protocol is characterized by its exquisite chemo‐ and regioselectivity, broad substrate scope and good functional group compatibility. Mechanistic studies confirmed that the regioselectivity and reactivity observed are a result of electro‐induced ring‐opening of aziridines under electroreductive conditions to generate a benzyl radical intermediate as the active species. Furthermore, this strategy also enables cross‐coupling with CO 2 to access β ‐amino acids under mild conditions.
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Scalable and sustainable electrochemical allylic C–H oxidation
Evan J. Horn, Brandon R. Rosen, Yong Chen et al. · Nature · 2016 · 738 citations · Full text
Metal-catalyzed electrochemical diazidation of alkenes
Niankai Fu, Gregory S. Sauer, Ambarneil Saha et al. · Science · 2017 · 684 citations