Amine-mediated Bond Cleavage in Oxidized Lignin Models

ChemSusChem
Hongji LiFeng Wang

Abstract

Introducing amines/ammonia into lignin cracking will allow novel bond cleavage pathways. Herein, a method of amines/ammonia-mediated bonds cleavage in oxidized lignin β-O-4 models was studied using copper catalyst under room temperature, demonstrating the effect of amine source on selectivity of products. For primary and secondary aliphatic amines, lignin ketone models underwent oxidative C α -C β bond cleavage and C α -N bond formation to generate aromatic amides. For ammonia, the competition between oxygen and ammonia determined the selectivity between C α -N and C β -N bond formation, generating amides and α-keto amides, respectively. For tertiary amines, the lignin models underwent oxidative C α -C β bond cleavage to benzoic acids. Control experiments indicate that amines act as nucleophiles attacking at C α or C β position of the oxidized β-O-4 linkage to be cleaved. This study represents a novel example that the breakage of oxidized lignin model can be regulated by amines with copper catalyst.

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Citations

Jul 24, 2021·Angewandte Chemie·Bo ZhangTao Zhang

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