Organocatalytic chemoselective primary alcohol oxidation and subsequent cleavage of lignin model compounds and lignin

Saumya Dabral, José G. Hernández, Paul C. J. Kamer, Carsten Bolm

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Abstract

A one-pot two-step degradation of lignin β-O-4 model compounds initiated by preferred oxidation of the primary over the secondary hydroxyl groups with a TEMPO/DAIB system has been developed [TEMPO=2,2,6,6-tetramethylpiperidine-N-oxyl, DAIB=(diacetoxy)iodobenzene]. The oxidised products are then cleaved by proline-catalysed retro-aldol reactions. This degradation methodology produces simple aromatics in good yields from lignin model compounds at room temperature with an extension to organosolv beech-wood lignin (L1) resulting in known cleavage products.
Original languageEnglish
Pages (from-to)2707–2713
JournalCHEMSUSCHEM
Volume10
Issue number13
Early online date14 Jun 2017
DOIs
Publication statusPublished - 10 Jul 2017

Keywords

  • Alcohol oxidation
  • Bond cleavage
  • Lignin
  • One-pot
  • Organocatalysis
  • Retro-aldol

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  • SUBICAT: SUBICAT

    Kamer, P. C. J.

    Marie Curie Fellowships

    1/10/1330/09/17

    Project: Standard

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