Issue 45, 2021

Organic amine mediated cleavage of Caromatic–Cα bonds in lignin and its platform molecules

Abstract

The activation and cleavage of C–C bonds remains a critical scientific issue in many organic reactions and is an unmet challenge due to their intrinsic inertness and ubiquity. Meanwhile, it is crucial for the valorization of lignin into high-value chemicals. Here, we proposed a novel strategy to enhance the Caromatic–Cα bond cleavage by pre-functionalization with amine sources, in which an active amine intermediate is first formed through Markovnikov hydroamination to reduce the dissociation energy of the Caromatic–Cα bond which is then cleaved to form target chemicals. More importantly, this strategy provides a method to achieve the maximum utilization of the aromatic nucleus and side chains in lignin or its platform molecules. Phenols and N,N-dimethylethylamine compounds with high yields were produced from herbaceous lignin or the p-coumaric acid monomer in the presence of industrially available dimethylamine (DMA).

Graphical abstract: Organic amine mediated cleavage of Caromatic–Cα bonds in lignin and its platform molecules

Supplementary files

Article information

Article type
Edge Article
Submitted
22 Sep 2021
Accepted
29 Oct 2021
First published
03 Nov 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 15110-15115

Organic amine mediated cleavage of Caromatic–Cα bonds in lignin and its platform molecules

Y. Xin, X. Shen, M. Dong, X. Cheng, S. Liu, J. Yang, Z. Wang, H. Liu and B. Han, Chem. Sci., 2021, 12, 15110 DOI: 10.1039/D1SC05231D

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