An efficient approach to biomass-based tertiary amines by direct and consecutive reductive amination of furfural

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 effi-cient 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 consec-utive 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 high-lights a powerful, elegant, and attractive approach to biomass-based tertiary amines for a sustainable extension of amine chemistry. (c) 2022 Elsevier Inc.All rights reserved.

Automated summary

This research demonstrates a highly efficient and convenient strategy for the synthesis of various biomass-based tertiary amines using a rhodium phosphide catalyst. The one-pot reaction achieves excellent yields and offers a sustainable approach to extend amine chemistry.