Production of alkoxyl-functionalized cyclohexylamines from lignin-derived guaiacols

Bingxiao Zheng; Haihong Wu; Jinliang Song; Wei Wu; Xuelei Mei; Kaili Zhang; Caiyun Xu; Jiao Xu; Mingyuan He; Buxing Han

doi:10.1039/D1GC02790E

Production of alkoxyl-functionalized cyclohexylamines from lignin-derived guaiacols†

Bingxiao Zheng,^a Haihong Wu,

*^a Jinliang Song,

*^b Wei Wu,^a Xuelei Mei,^a Kaili Zhang,^a Caiyun Xu,^a Jiao Xu,^a Mingyuan He^a and Buxing Han

*^ab

Author affiliations

* Corresponding authors

^a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China
E-mail: hhwu@chem.ecnu.edu.cn, hanbx@iccas.ac.cn

^b Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid and Interface and Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
E-mail: songjl@iccas.ac.cn

Abstract

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.

Green Chemistry

Production of alkoxyl-functionalized cyclohexylamines from lignin-derived guaiacols†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Production of alkoxyl-functionalized cyclohexylamines from lignin-derived guaiacols

Social activity

Search articles by author

Spotlight

Advertisements