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Theoretical studies on the mechanism of Pd2+-catalyzed regioselective C–H acylation of azoxybenzenes with α-oxocarboxylic acids

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Abstract

The reaction mechanism of the Pd2+-catalyzed regioselective C(sp2)–H acylation of azoxybenzenes with α-oxocarboxylic acids has been studied by density functional theory (DFT) calculations. This reaction mechanism involves five major steps: C–H activation, deprotonation, decarboxylation, reductive elimination and oxidation. Our calculation results indicate that the N-coordinated pathway is better than the O-coordinated pathway, which can be interpreted by distortion-interaction analysis of the C–H bond activation transition states. Furthermore, we also suggest that the C–H bond acylation of aryl 1 is more favorable than that of aryl 2, which can be attributed to the fact that five-membered ring transition states are more favorable than four-membered ring transition states and the ON-group has positive charge.

Graphical abstract: Theoretical studies on the mechanism of Pd2+-catalyzed regioselective C–H acylation of azoxybenzenes with α-oxocarboxylic acids

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Publication details

The article was received on 02 Aug 2018, accepted on 10 Sep 2018 and first published on 11 Sep 2018


Article type: Paper
DOI: 10.1039/C8DT03154A
Citation: Dalton Trans., 2018, Advance Article
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    Theoretical studies on the mechanism of Pd2+-catalyzed regioselective C–H acylation of azoxybenzenes with α-oxocarboxylic acids

    P. Hu, S. Wang, Y. Wang, C. Deng and W. Zhang, Dalton Trans., 2018, Advance Article , DOI: 10.1039/C8DT03154A

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