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...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie 2019-05, Vol.131 (21), p.7073-7077
Main Authors: Zhang, Qinglin, Chang, Xihao, Peng, Lingzi, Guo, Chang
Format: Article
Language:English
Subjects:
Adducts
Alkylation
Anodizing
Asymmetrische Katalyse
Catalysis
Chemistry
Electrochemistry
Elektrochemie
Lewis acid
Lewis-Säuren
Nickel
Organic chemistry
Oxidation
Radikale
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. Elektrifizierend: Mit einem chiralen Ni‐Katalysator wurde eine effiziente asymmetrische Elektrosynthese mit hohen Ausbeuten und hervorragenden Enantioselektivitäten entwickelt. Mechanistische Studien deuten darauf hin, dass das Lewis‐Säure‐gebundene radikalische Zwischenprodukt, das aus einer anodischen Ein‐Elektronen‐Oxidation stammt, selektiv mit einer benzylischen Radikalspezies reagiert, um die gewünschten Addukte zu bilden.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201901801