Efficient Synthesis of 2-Pentylamine via Hydrogenolysis-Reductive Amination of 2-Methylfuran

Nitrogen-containing chemicals have a wide range of applications. The development of high-value-added nitrogen-containing compounds using biobased raw materials is fully aligned with the principles of green chemistry. In this paper, the catalytic system, reaction mechanism, and process optimization of 2-pentylamine synthesis by hydrogenolysis-reductive amination of 2-methylfuran as a template compound were systematically studied. Under the optimized conditions, the conversion of 2-methylfuran is 85.5%, the selectivity of 2-pentamine is 69.8%, and the selectivity of 1-pentamine is 8.70%. Mechanistic studies indicate that this reaction proceeds via the hydrogenolysis of the furan ring to form a C═O-containing intermediate, which is followed by reductive amination to yield 2-pentanamine. Furthermore, this strategy is extended to hydrogenolysis-reductive amination of furfuryl alcohol. This study confirmed that hydrogenolysis-reductive amination can efficiently convert biobased furan compounds into high-value nitrogen-containing compounds, aligning with the principles of green chemistry and providing a new approach for the sustainable synthesis of nitrogen-containing functional chemicals.