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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Published in:ACS catalysis 2018-10, Vol.8 (10), p.9370-9375
Main Authors: Hu, Xia, Zhang, Guoting, Bu, Faxiang, Nie, Lei, Lei, Aiwen
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Language:English
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cited_by cdi_FETCH-LOGICAL-a346t-d13f6c722123360deb457404a5ca52965473b9e4e7e82aa795bf0b8ed80c4db3
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creator Hu, Xia
Zhang, Guoting
Bu, Faxiang
Nie, Lei
Lei, Aiwen
description 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.
doi_str_mv 10.1021/acscatal.8b02847
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