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

doi:10.1002/cssc.201700703

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

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	2707–2713
Journal	CHEMSUSCHEM
Volume	10
Issue number	13
Early online date	14 Jun 2017
DOIs	https://doi.org/10.1002/cssc.201700703
Publication status	Published - 10 Jul 2017

Keywords

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

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Kamer_2017_CHEMSUSCHEM_PrimaryAlcohol_AAM
© 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
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Cite this

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title = "Organocatalytic chemoselective primary alcohol oxidation and subsequent cleavage of lignin model compounds and lignin",

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.",

keywords = "Alcohol oxidation, Bond cleavage, Lignin, One-pot, Organocatalysis, Retro-aldol",

author = "Saumya Dabral and Hern{\'a}ndez, {Jos{\'e} G.} and Kamer, {Paul C. J.} and Carsten Bolm",

note = "This 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. ",

year = "2017",

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doi = "10.1002/cssc.201700703",

language = "English",

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TY - JOUR

T1 - Organocatalytic chemoselective primary alcohol oxidation and subsequent cleavage of lignin model compounds and lignin

AU - Dabral, Saumya

AU - Hernández, José G.

AU - Kamer, Paul C. J.

AU - Bolm, Carsten

N1 - This 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.

PY - 2017/7/10

Y1 - 2017/7/10

N2 - 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.

AB - 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.

KW - Alcohol oxidation

KW - Bond cleavage

KW - Lignin

KW - One-pot

KW - Organocatalysis

KW - Retro-aldol

UR - http://onlinelibrary.wiley.com/doi/10.1002/cssc.201700703/full#footer-support-info

U2 - 10.1002/cssc.201700703

DO - 10.1002/cssc.201700703

M3 - Article

SN - 1864-564X

VL - 10

SP - 2707

EP - 2713

JO - CHEMSUSCHEM

JF - CHEMSUSCHEM

IS - 13

ER -

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

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

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