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Computational and experimental studies on copper-mediated selective cascade C–H/N–H annulation of electron-deficient acrylamide with arynes

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Abstract

An efficient and convenient copper-mediated method has been developed to achieve direct cascade C–H/N–H annulation to synthesize 2-quinolinones from electron-deficient acrylamides and arynes. This method highlights an emerging but simple strategy to transform inert C–H bonds into versatile functional groups in organic synthesis to provide a new method of synthesizing 2-quinolinones efficiently. Mechanistic investigations by experimental and density functional theory (DFT) studies suggest that an organometallic C–H activation via a Cu(III) intermediate is likely to be involved in the reaction.

Graphical abstract: Computational and experimental studies on copper-mediated selective cascade C–H/N–H annulation of electron-deficient acrylamide with arynes

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Publication details

The article was received on 31 Oct 2018, accepted on 26 Nov 2018 and first published on 26 Nov 2018


Article type: Communication
DOI: 10.1039/C8CC08708C
Citation: Chem. Commun., 2019, Advance Article
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    Computational and experimental studies on copper-mediated selective cascade C–H/N–H annulation of electron-deficient acrylamide with arynes

    C. Chen, Y. Hao, T. Zhang, J. Pan, J. Ding, H. Xiang, M. Wang, T. Ding, A. Duan and S. Zhang, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C8CC08708C

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