Organocatalytic chemoselective primary alcohol oxidation and subsequent cleavage of lignin model compounds and lignin
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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.
Dabral , S , Hernández , J G , Kamer , P C J & Bolm , C 2017 , ' Organocatalytic chemoselective primary alcohol oxidation and subsequent cleavage of lignin model compounds and lignin ' CHEMSUSCHEM , vol. 10 , no. 13 , pp. 2707–2713 . DOI: 10.1002/cssc.201700703
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/10.1002/cssc.201700703
DescriptionThis research was supported by the European Union (Marie Curie ITN “SuBiCat” PITN-GA-2013-607044, S.D.) and by the Distinguished Professorship Program at RWTH Aachen University funded by the Excellence Initiative of the German federal and state governments.
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