Asymmetric Lewis Acid Catalyzed Electrochemical Alkylation. Issue 21 (10th April 2019)

• Record Type: Journal Article
• Authors: Zhang, Qinglin; Chang, Xihao; Peng, Lingzi; Guo, Chang
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 21(2019)
• Page Start: 6999
• Page End: 7003
• Publication Date: 2019-04-10
• Subjects: asymmetric catalysis -- electrochemistry -- Lewis acids -- nickel -- radicals; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201901801
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : 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.