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Issue 11, 2016
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Chemoselective transfer hydrogenation of α,β-unsaturated carbonyl compounds using potassium formate over amine-grafted Ru/AlO(OH) catalysts

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Abstract

Grafting of 3-(2-aminoethylamino)propyltrimethoxysilane onto Ru/AlO(OH) resulted in an active and highly chemoselective heterogeneous catalyst for the transfer hydrogenation of α,β-unsaturated carbonyl compounds to the corresponding allylic alcohols. Potassium formate was used as a sustainable hydrogen donor. A range of substrates including cinnamaldehyde, α-amylcinnamaldehyde, citral, 3-methyl-2-butenal, trans-2-pentenal, and trans-hexenal were selectively hydrogenated at the C[double bond, length as m-dash]O moiety with >96% selectivity. In comparison, the unmodified 1 wt% Ru/AlO(OH) catalyzed hydrogenation of cinnamaldehyde at the C[double bond, length as m-dash]C bond, yielding 3-phenylpropanal as the product. Higher loaded samples with 2–10 wt% Ru exhibited 20–25% selectivity to cinnamyl alcohol. The results show that low coordination sites were more selective to hydrogenation of the internal C[double bond, length as m-dash]C than the terminal C[double bond, length as m-dash]O bond. Immobilization of the amine via chemical bonding with hydroxyl groups of the AlO(OH) support blocks adjacent exposed metal sites, increasing the chemoselective reduction of C[double bond, length as m-dash]O. Optimum results were achieved at an amine/Ru ratio of 6. The catalyst maintained high activity and chemoselectivity even after five cycles.

Graphical abstract: Chemoselective transfer hydrogenation of α,β-unsaturated carbonyl compounds using potassium formate over amine-grafted Ru/AlO(OH) catalysts

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Supplementary files

Article information


Submitted
04 Sep 2015
Accepted
17 Dec 2015
First published
21 Dec 2015

Catal. Sci. Technol., 2016,6, 3806-3813
Article type
Paper
Author version available

Chemoselective transfer hydrogenation of α,β-unsaturated carbonyl compounds using potassium formate over amine-grafted Ru/AlO(OH) catalysts

Y. Gao, J. Wang, A. Han, S. Jaenicke and G. K. Chuah, Catal. Sci. Technol., 2016, 6, 3806
DOI: 10.1039/C5CY01475A

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