Precise control of selective hydrogenation of α,β-unsaturated aldehydes in water mediated by ammonia borane

Zhou, Yangyang, Chen, Chen, Li, Qiling, Wei, Ting, Liu, Yanbo, Zeng, Zebing, Bradshaw, Darren, Zhang, Bing and Huo, Jia (2022) Precise control of selective hydrogenation of α,β-unsaturated aldehydes in water mediated by ammonia borane. Applied Catalysis B: Environmental, 311, [121348]. (doi:10.1016/j.apcatb.2022.121348).

Abstract

Hydrogenation of unsaturated biomass in a control manner is highly desirable but challenging, especially under mild conditions. We here report selective hydrogenation of α,β-unsaturated aldehydes (UALs), featuring a precise control of all potential products by adjustment of the role of ammonia borane (AB) in transfer and/or catalytic hydrogenation. The hydrogenation can be readily operated in neat water without using any external H2-source, because AB as the H2-source is favorable in aqueous solution. Impressively, unsaturated alcohols are prepared in 100% conversion by the room-temperature transfer hydrogenation of UALs with AB, while saturated aldehydes are obtained in 100% conversion and > 90% selectivity with high activity (i.e., turnover frequency = 0.98 s−1 for cinnamaldehyde), by the catalytic hydrogenation with H2 released from AB and Pd immobilized on two-dimensional metal organic layer. On the other hand, UALs can be completely converted into the saturated alcohols through a combination of transfer and catalytic hydrogenation in one pot. This strategy can be extended to more than 8 types of UALs, and provides a facile way to fine-control the selective hydrogenation of unsaturated compounds with competing bonds.

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Contributors

Author: Darren Bradshaw

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