Synthesis of amine derivatives from furoin and furil over Ru/Al2O3 catalyst

Gao, Li, Delle Piane, Massimo, Corno, Marta, Jiang, Fan, Raja, Robert and Pera Titus, Marc 2024. Synthesis of amine derivatives from furoin and furil over Ru/Al2O3 catalyst. Catalysis Science & Technology 14 (9) , pp. 2593-2599. 10.1039/D3CY01605F

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Abstract

The direct/reductive amination of carbohydrate-based furoin and furil with NH3/H2 was investigated to access amine derivatives. In the sole presence of NH3, cyclic amines, i.e. 2,3,5,6-tetra(furan-2-yl)pyrazine and 2,2’-bipyridine-3,3’-diol, were generated as main products from furoin and furil, respectively. Over Ru/Al2O3 under NH3/H2, 2-amino-1,2-di(furan-2-yl)ethan-1-ol (i.e. alcohol-amine) was generated as main product with 47% yield at 140 °C for 2 h starting from furoin. The catalyst could be recycled for at least three consecutive runs. An alcohol-imine was the main intermediate that undewent tautomerization to alcohol-enamine/keto-amine leading to cyclic by-products by self-condensation. Supported by DFT calculations, the reactivity of the alcohol-imine intermediate was rationalized by its preferential adsorption on Ru centers via the NH group with the OH group pointing away from the surface, resulting in the formation of alcohol-amine as main product. By combining Ru/Al2O3 and a silica-anchored N-heterocyclic carbene (NHC) catalyst, 2-amino-1,2-di(furan-2-yl)ethan-1-ol could be accessed with 42% overall yield in a single reactor.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry Cardiff Catalysis Institute (CCI)
Publisher:	Royal Society of Chemistry
ISSN:	2044-4753
Funders:	European Union's Horizon 2020 research and innovation program under grant agreement N. 720783-MULTI2HYCAT
Date of First Compliant Deposit:	20 March 2024
Date of Acceptance:	13 February 2024
Last Modified:	04 Jun 2024 13:36
URI:	https://orca.cardiff.ac.uk/id/eprint/167402

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