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C[BOND]C or C[BOND]O Bond Cleavage in a Phenolic Lignin Model Compound: Selectivity Depends on Vanadium Catalyst

Authors

  • Dr. Susan K. Hanson,

    Corresponding author
    1. Chemistry and Bioscience Divisions, Los Alamos National Laboratory, MS J582, Los Alamos 87545 (USA)
    • Chemistry and Bioscience Divisions, Los Alamos National Laboratory, MS J582, Los Alamos 87545 (USA)
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  • Dr. Ruilian Wu,

    1. Chemistry and Bioscience Divisions, Los Alamos National Laboratory, MS J582, Los Alamos 87545 (USA)
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  • Dr. Louis A. “Pete” Silks

    Corresponding author
    1. Chemistry and Bioscience Divisions, Los Alamos National Laboratory, MS J582, Los Alamos 87545 (USA)
    • Chemistry and Bioscience Divisions, Los Alamos National Laboratory, MS J582, Los Alamos 87545 (USA)
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  • This work was supported by Los Alamos National Laboratory LDRD (20100160ER). We would also like to thank the NSF Center for Enabling New Technologies through Catalysis.

Abstract

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The aerobic oxidation of a phenolic lignin model compound with a vanadium catalyst results in the oxidative cleavage of the C[BOND]C bond between the aryl ring and the adjacent hydroxy-substituted carbon atom (see scheme). Labeling experiments indicate key mechanistic differences to a previously reported related C[BOND]O bond cleavage reaction. The selectivity in C[BOND]C versus C[BOND]O bond cleavage depends on the choice of the vanadium catalyst.

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