An efficient approach to biomass-based tertiary amines by direct and consecutive reductive amination of furfural
2022
Lin, Chuncheng | Zhou, Jiamin | Zheng, Zhangfan | Chen, Jinzhu
Tertiary amines, currently obtained from fossil resources by a multi-step synthetic method, are important compounds in both chemical industry and organic transformations. Herein, we demonstrated highly efficient and convenient strategy to various biomass-based tertiary amines in excellent yields (85–95%) by a direct and consecutive reductive amination of furfural with various amines in one-pot using rhodium phosphide (Rh₂P) catalyst. Typically, biomass-based tris(2-furanylmethyl)amine in 92% yield was directly obtained from furfural and HCOONH₄ in one-step. Time-dependent reaction profiles suggested a consecutive amination/hydrogenation pathway with furfurylamine-derived Schiff base and secondary amine as successively detected intermediates. The superiority of Rh₂P was ascribed to its excellent low-temperature hydrogenation activity, which is structurally attributed to an efficient electron-transfer from P atoms (on the P-terminated Rh₂P) to their bonded and dissociated H atoms. This research thus highlights a powerful, elegant, and attractive approach to biomass-based tertiary amines for a sustainable extension of amine chemistry.
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