Electrochemical-Oxidation-Induced Site-Selective Intramolecular C(sp3)–H Amination

The cross-coupling of C­(sp3)–H and N–H represents one of the most straightforward approaches to construct saturated nitrogen-containing compounds. The additional oxidants or halogenated reagents are generally required in such processes. Herein, we developed an electrochemical oxidative intramolecul...

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Bibliographic Details
Published in:ACS catalysis 2018-10, Vol.8 (10), p.9370-9375
Main Authors: Hu, Xia, Zhang, Guoting, Bu, Faxiang, Nie, Lei, Lei, Aiwen
Format: Article
Language:English
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Summary:The cross-coupling of C­(sp3)–H and N–H represents one of the most straightforward approaches to construct saturated nitrogen-containing compounds. The additional oxidants or halogenated reagents are generally required in such processes. Herein, we developed an electrochemical oxidative intramolecular C­(sp3)–H amination of amides by employing a carbon rod anode and a platinum plate cathode in an undivided cell under constant-current electrolysis conditions. Tetrabutylammonium acetate was not only employed as an electrolyte, but also can form the intermolecular hydrogen bond with amide and promote cleavage of the N–H bond. The additional oxidants and N-halogenation step can be obviated in this methodology. A variety of benzylic and nonactivated tertiary, secondary, primary C­(sp3)–H amination can be achieved with good yields.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.8b02847