Asymmetric Lewis Acid Catalyzed Electrochemical Alkylation

Lewis‐acid catalysis and electrochemistry represent two powerful fields that have found widespread application in organic chemistry. Reported herein is an asymmetric electrosynthesis in combination with a chiral Ni catalyst leading to an intermolecular alkylation reaction in good yields with excelle...

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Veröffentlicht in:Angewandte Chemie International Edition 2019-05, Vol.58 (21), p.6999-7003
Hauptverfasser: Zhang, Qinglin, Chang, Xihao, Peng, Lingzi, Guo, Chang
Format: Artikel
Sprache:eng
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Zusammenfassung:Lewis‐acid catalysis and electrochemistry represent two powerful fields that have found widespread application in organic chemistry. Reported herein is an asymmetric electrosynthesis in combination with a chiral Ni catalyst leading to an intermolecular alkylation reaction in good yields with excellent enantioselectivities (up to 97 % ee). Mechanistic studies suggest that the Lewis‐acid‐bound radical intermediate from a single‐electron anodic oxidation selectively reacts with the benzylic radical species to generate the desired adducts. Electrifying: An efficient asymmetric electrosynthesis was developed with high yields and excellent enantioselectivities by using a chiral Ni catalyst. Mechanistic studies suggest that the Lewis‐acid‐bound radical intermediate, from a single‐electron anodic oxidation, selectively reacts with a benzylic radical species to generate the desired adducts.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201901801