Palladium-catalyzed synthesis of 4-cyclohexylmorpholines from reductive coupling of aryl ethers and lignin model compounds with morpholines

Bingxiao Zheng; Jinliang Song; Haihong Wu; Shitao Han; Jianxin Zhai; Kaili Zhang; Wei Wu; Caiyun Xu; Mingyuan He; Buxing Han

doi:10.1039/D0GC03188G

Palladium-catalyzed synthesis of 4-cyclohexylmorpholines from reductive coupling of aryl ethers and lignin model compounds with morpholines†

Bingxiao Zheng,^a Jinliang Song,

^b Haihong Wu,

*^a Shitao Han,^a Jianxin Zhai,^a Kaili Zhang,^a Wei Wu,^a Caiyun Xu,^a Mingyuan He^a and Buxing Han

*^ab

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* 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

Abstract

This work describes the highly efficient Pd-catalyzed direct coupling of aryl ethers (including the typical lignin model compounds) and morpholines to produce 4-cyclohexylmorpholines, a useful class of fine chemicals. Without employing any acidic additives, various 4-cyclohexylmorpholines could be synthesized with good yields from a variety of aryl ethers using H₂ as a hydrogen resource. A mechanism study revealed that the desired product was formed via the cleavage of the C(Ar)–O bonds to generate the corresponding cyclohexanones and subsequent reductive amination.

This article is part of the themed collection: 2021 Green Chemistry Hot Articles

Green Chemistry

Palladium-catalyzed synthesis of 4-cyclohexylmorpholines from reductive coupling of aryl ethers and lignin model compounds with morpholines†

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Palladium-catalyzed synthesis of 4-cyclohexylmorpholines from reductive coupling of aryl ethers and lignin model compounds with morpholines

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