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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).

SUBMITTER: Xin Y 

PROVIDER: S-EPMC8612377 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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Organic amine mediated cleavage of C<sub>aromatic</sub>-C<sub>α</sub> bonds in lignin and its platform molecules.

Xin Yu Y   Shen Xiaojun X   Dong Minghua M   Cheng Xiaomeng X   Liu Shulin S   Yang Junjuan J   Wang Zhenpeng Z   Liu Huizhen H   Han Buxing B  

Chemical science 20211103 45

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 C<sub>aromatic</sub>-C<sub>α</sub> bond cleavage by pre-functionalization with amine sources, in which an active amine intermediate is first formed through Markovnikov hydroamination to reduc  ...[more]

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