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Lignol Cleavage by Pd/C Under Mild Conditions and Without Hydrogen: A Role for Benzylic C[BOND]H Activation?

Authors

  • Dr. Xiaoyuan Zhou,

    1. Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL 61801 (USA), Fax: (+1) 217-244-3186
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  • Dr. Joyee Mitra,

    1. Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL 61801 (USA), Fax: (+1) 217-244-3186
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  • Prof. Thomas B. Rauchfuss

    Corresponding author
    1. Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL 61801 (USA), Fax: (+1) 217-244-3186
    • Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL 61801 (USA), Fax: (+1) 217-244-3186===

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Abstract

The cleavage of C[BOND]O bonds in lignin model compounds without hydrogen was developed using the commercially available Pd/C. Hydrogen donor solvents are helpful for this reaction through transfer hydrogenation, but not necessary. A redox neutral process that utilizes the internal hydrogen source for the cleavage is also possible. An initial mechanistic study indicates that the β-benzylic-H atom in the substrate plays a critical role and that the present system undergoes a process different from previous reports.

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