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Issue 14, 2018
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Transformation of lignin model compounds to N-substituted aromatics via Beckmann rearrangement

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Abstract

Here we present the highly effective cleavage of C–C bonds in lignin model compounds for the production of N-substituted aromatics in up to 96% total yield, including benzonitriles and amides, via oxime formation followed by Beckmann rearrangement (BR). The amides could be further hydrolyzed to anilines (>92% yield) and carboxylic acids (>90% yield), respectively. In addition, the employment of a substrate with a γ-OH group will lead to the formation of C-2 monosubstituted oxazole. A one-pot process involving the BR reaction and hydrolysis has also been developed to directly afford an up to 96% total yield of benzonitriles, benzamides, and anilines. This strategy enabled us to successfully apply the BR reaction to the degradation of lignin model compounds to N-functionalized aromatic products under mild conditions.

Graphical abstract: Transformation of lignin model compounds to N-substituted aromatics via Beckmann rearrangement

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Publication details

The article was received on 22 Mar 2018, accepted on 12 Jun 2018 and first published on 14 Jun 2018


Article type: Paper
DOI: 10.1039/C8GC00920A
Citation: Green Chem., 2018,20, 3318-3326
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    Transformation of lignin model compounds to N-substituted aromatics via Beckmann rearrangement

    Y. Wang, Y. Du, J. He and Y. Zhang, Green Chem., 2018, 20, 3318
    DOI: 10.1039/C8GC00920A

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