Electrochemical α‐Functionalization of N‐Aryl‐Activated Tertiary Amines

Numerous appropriately substituted pyridyl or phenyl groups serve as a particularly advantageous activation motif for the electrochemical oxidation of amines. Such groups enable a general, mild method for the electrochemical α‐functionalization of tertiary amines across numerous activating groups an...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-09, Vol.366 (17), p.3653-3663
Main Authors: Wang, Feijun, Frankowski, Kevin J.
Format: Article
Language:English
Subjects:
Amines
C−H activation
Electrochemical oxidation
Functional groups
Natural products
Nitrogen heterocycles
Nucleophiles
Nucleophilic addition
Synthetic methods
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Summary:Numerous appropriately substituted pyridyl or phenyl groups serve as a particularly advantageous activation motif for the electrochemical oxidation of amines. Such groups enable a general, mild method for the electrochemical α‐functionalization of tertiary amines across numerous activating groups and amine scaffolds. Notably, the method accommodates an unprecedented range of nucleophile classes, allowing for the introduction of diverse functional groups to the readily prepared amine substrates. The utility of this method is then demonstrated through applications to unsymmetrical bisfunctionalization, site‐selective functionalization of N‐pyridyl amines vs. other activated amines, a formal synthesis of ivosidenib and the diversification of FDA‐approved drugs or natural product substrates.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202400720