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Issue 13, 2017
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Highly effective C–C bond cleavage of lignin model compounds

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Abstract

A highly effective method is developed for the C–C bond cleavage of lignin model compounds. The inert Cα–Cβ or Cα–Cphenyl bond of oxidized lignin model compounds was successfully converted to an active ester bond through the classic organic name reaction, Baeyer–Villiger (BV) oxidation, and thus acetal esters and aryl esters were produced in high yields (up to 99%) at room temperature. Next, K2CO3 catalyzed the alcoholysis of the resulting ester products at 45 °C, affording various useful chemical platforms in excellent yields (up to 99%), such as phenols and multifunctional esters. This method uses commercially available reagents, is transition-metal free and simple, but highly effective, and involves mild reaction conditions.

Graphical abstract: Highly effective C–C bond cleavage of lignin model compounds

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Publication details

The article was received on 19 Mar 2017, accepted on 19 May 2017 and first published on 22 May 2017


Article type: Paper
DOI: 10.1039/C7GC00844A
Citation: Green Chem., 2017,19, 3135-3141
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    Highly effective C–C bond cleavage of lignin model compounds

    Y. Wang, Q. Wang, J. He and Y. Zhang, Green Chem., 2017, 19, 3135
    DOI: 10.1039/C7GC00844A

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