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Issue 2, 2018
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Copper-catalyzed synthesis of benzanilides from lignin model substrates 2-phenoxyacetophenones under an air atmosphere

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Abstract

The synthesis of chemicals from biomass-derived compounds is an interesting and challenging topic. In this work, using the lignin-derived 2-phenoxyacetophenones as the feedstock we present a novel approach for the synthesis of benzanilides via the reaction of 2-phenoxyacetophenones with anilines catalyzed by CuCl2 in DMSO at 120 °C under an air atmosphere. This approach has wide scope for 2-phenoxyacetophenones and anilines, and various benzanilides accompanied by the corresponding phenols could be obtained in high yields via changing the 2-phenoxyacetophenones and anilines. The reaction mechanism study indicated that the oxidative cleavage of the C–C bond in 2-phenoxyacetophenones and the formation of a C–N bond occurred simultaneously in the reaction process, resulting in the formation of benzanilides together with phenols.

Graphical abstract: Copper-catalyzed synthesis of benzanilides from lignin model substrates 2-phenoxyacetophenones under an air atmosphere

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Publication details

The article was received on 16 Jul 2017, accepted on 05 Dec 2017 and first published on 06 Dec 2017


Article type: Paper
DOI: 10.1039/C7NJ02589K
Citation: New J. Chem., 2018,42, 1223-1227
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    Copper-catalyzed synthesis of benzanilides from lignin model substrates 2-phenoxyacetophenones under an air atmosphere

    X. Liu, H. Zhang, C. Wu, Z. Liu, Y. Chen, B. Yu and Z. Liu, New J. Chem., 2018, 42, 1223
    DOI: 10.1039/C7NJ02589K

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