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Issue 14, 2017
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Selective hydration of asymmetric internal aryl alkynes without directing groups to α-aryl ketones over Cu-based catalyst

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Abstract

Hydration of internal aryl alkynes to provide aryl carbonyl compounds is a class of important reactions and has been widely investigated. However, the hydration of asymmetric internal aryl alkynes without directing groups usually gives an aryl ketone or a mixture of aryl ketone and α-aryl ketone. High regioselectivity to α-aryl ketone is a great challenge and has not been reported. Herein, we found that CuBr and p-fluoroaniline had an excellent synergistic effect in catalyzing the hydration of internal aryl alkynes without directing groups to α-aryl ketones with regioselectivity up to more than 90%, which is much greater than those reported. The reaction mechanism was proposed, and the reason for the high selectivity was clarified by a combination of density functional theory (DFT) calculation, condensed dual descriptor (CDD) study, and experimental results. It was demonstrated that the formations of α-aryl ketone and aryl ketone were promoted by different catalytic active species, CuBr and CuBr[p-fluoroaniline], respectively. CuBr enlarged the difference of electron population on the two triple-bond carbon atoms, resulting in α-aryl ketones as the main products.

Graphical abstract: Selective hydration of asymmetric internal aryl alkynes without directing groups to α-aryl ketones over Cu-based catalyst

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Publication details

The article was received on 10 Feb 2017, accepted on 27 May 2017 and first published on 29 May 2017


Article type: Paper
DOI: 10.1039/C7NJ00486A
Citation: New J. Chem., 2017,41, 6290-6295
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    Selective hydration of asymmetric internal aryl alkynes without directing groups to α-aryl ketones over Cu-based catalyst

    Q. Mei, H. Liu, M. Hou, H. Liu and B. Han, New J. Chem., 2017, 41, 6290
    DOI: 10.1039/C7NJ00486A

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