Synthesis of piperidines and pyridine from furfural over a surface single-atom alloy Ru1CoNP catalyst

Haifeng Qi, Yurou Li, Zhitong Zhou, Yueqiang Cao, Fei Liu, Weixiang Guan, Leilei Zhang, Xiaoyan Liu, Lin Li, Yang Su, Kathrin Junge, Xuezhi Duan (), Matthias Beller (), Aiqin Wang () and Tao Zhang
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Haifeng Qi: Chinese Academy of Sciences
Yurou Li: East China University of Science and Technology
Zhitong Zhou: Chinese Academy of Sciences
Yueqiang Cao: East China University of Science and Technology
Fei Liu: Chinese Academy of Sciences
Weixiang Guan: Chinese Academy of Sciences
Leilei Zhang: Chinese Academy of Sciences
Xiaoyan Liu: Chinese Academy of Sciences
Lin Li: Chinese Academy of Sciences
Yang Su: Chinese Academy of Sciences
Kathrin Junge: Albert-Einstein-Straße 29a
Xuezhi Duan: East China University of Science and Technology
Matthias Beller: Albert-Einstein-Straße 29a
Aiqin Wang: Chinese Academy of Sciences
Tao Zhang: Chinese Academy of Sciences

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract The sustainable production of value-added N-heterocycles from available biomass allows to reduce the reliance on fossil resources and creates possibilities for economically and ecologically improved synthesis of fine and bulk chemicals. Herein, we present a unique Ru1CoNP/HAP surface single-atom alloy (SSAA) catalyst, which enables a new type of transformation from the bio-based platform chemical furfural to give N-heterocyclic piperidine. In the presence of NH3 and H2, the desired product is formed under mild conditions with a yield up to 93%. Kinetic studies show that the formation of piperidine proceeds via a series of reaction steps. Initially, in this cascade process, furfural amination to furfurylamine takes place, followed by hydrogenation to tetrahydrofurfurylamine (THFAM) and then ring rearrangement to piperidine. DFT calculations suggest that the Ru1CoNP SSAA structure facilitates the direct ring opening of THFAM resulting in 5-amino-1-pentanol which is quickly converted to piperidine. The value of the presented catalytic strategy is highlighted by the synthesis of an actual drug, alkylated piperidines, and pyridine.

Date: 2023
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DOI: 10.1038/s41467-023-42043-6

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