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Highly selective sp3 C–N bond activation of tertiary anilines modulated by steric and thermodynamic factors

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Abstract

A highly selective sp3 C–N cleavage of tertiary anilines was achieved using the TBN/TEMPO catalyst system. When N,N-diaklylanilines (alkyl, benzyl) were employed, the N–CH3 bond was selectively cleaved via radical C–H activation. Moreover, when the allyl group was installed, totally reverse selectivity was observed. It is worth noting that the solvent effect is also crucial to obtain high reaction efficiency and selectivity.

Graphical abstract: Highly selective sp3 C–N bond activation of tertiary anilines modulated by steric and thermodynamic factors

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Publication details

The article was received on 12 Sep 2017, accepted on 01 Nov 2017 and first published on 01 Nov 2017


Article type: Communication
DOI: 10.1039/C7GC02775C
Citation: Green Chem., 2017, Advance Article
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    Highly selective sp3 C–N bond activation of tertiary anilines modulated by steric and thermodynamic factors

    X. Jia, P. Li, Y. Shao, Y. Yuan, H. Ji, W. Hou, X. Liu and X. Zhang, Green Chem., 2017, Advance Article , DOI: 10.1039/C7GC02775C

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