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Enantioselective Nickel‐Catalyzed Electrochemical Radical Allylation

Qinglin Zhang, Kang Liang, Chang Guo

2022Angewandte Chemie International Edition56 citationsDOI

Abstract

A simplified and appealing strategy via a chiral catalyst to facilitate the electrochemical process and provide asymmetric induction of radical reactions is particularly desirable and would have potential applications in electrosynthesis, organic chemistry, and drug discovery. Here, we introduced a novel electrolytic system that diverts the standard ionic reactivity to new catalytic functions, enabling mechanistically distinct single-electron transfer-based enantioselective routes to exhibit a brand-new pattern of reactivity-electricity-driven asymmetric catalysis as a privileged chiral platform for enantioselective radical allylation. The nickel-catalyzed activation of nucleophiles triggered a single-electron transfer process to provide a chiral catalyst-bound radical cation intermediate, which could be applied as an alternative strategy for the development of stereocontrolled radical reactions.

Topics & Concepts

Enantioselective synthesisCatalysisElectrosynthesisCombinatorial chemistryChemistryReactivity (psychology)Ionic liquidNucleophileElectrochemistryNickelElectron transferRadical ionOrganic chemistryIonElectrodePhysical chemistryMedicinePathologyAlternative medicineRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsCO2 Reduction Techniques and Catalysts
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