Production of alkoxyl-functionalized cyclohexylamines from lignin-derived guaiacols
2021
Zheng, Bingxiao | Wu, Haihong | Song, Jinliang | Wu, Wei | Mei, Xuelei | Zhang, Kaili | Xu, Caiyun | Xu, Jiao | He, Mingyuan | Han, Buxing
The transformation of renewable lignin-based platform chemicals into value-added nitrogen-containing compounds is an emerging strategy for lignin utilization. However, multi-reactive sites on these platform chemicals make it challenging to control the product selectivity, thereby resulting in limited success. In this work, we developed the reductive-coupling of guaiacol, a typical lignin-based platform chemical, with amines and H₂ to synthesize methoxy-functionalized cyclohexylamines. It was demonstrated that Pd/C was a very efficient catalyst for this kind of reaction, and high yields of the target products can be obtained. Notably, this methodology can be applied for the reductive-coupling of various guaiacol analogues with amines to synthesize alkoxyl-functionalized cyclohexylamines with high yields. A mechanism study revealed that the reaction occurred through the generation of 2-methoxycyclohexanone and its subsequent reductive amination.
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