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Issue 21, 2018
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Ruthenium p-cymene complexes with α-diimine ligands as catalytic precursors for the transfer hydrogenation of ethyl levulinate to γ-valerolactone

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Abstract

The ruthenium compounds [(η6-p-cymene)RuCl{κ2N-(HCNR)2}]NO3 (R = 4-C6H4Me, [1]NO3; 4-C6H4OH, [2]NO3; C6H11[double bond, length as m-dash]Cy, [3]NO3; 4-C6H10OH, [4]NO3; tBu, [5]NO3) were prepared in high yields from [(p-cymene)RuCl2]2, AgNO3 and the appropriate α-diimine. Compounds [2]PF6 and [4]PF6 were obtained by a straightforward reaction of [(η6-p-cymene)RuCl(MeCN)0.66]PF6, [6]PF6, with α-diimine, whereas [4]BPh4 was obtained by metathesis between [4]NO3 and NaBPh4. All the ruthenium products were characterized by analytical methods, IR, NMR and UV-Vis spectroscopy; in addition, the structure of [1]NO3 was ascertained by an X-ray diffraction study. Compounds [1–4]NO3, [4]PF6 and [4]BPh4 were investigated as catalytic precursors in the transfer hydrogenation reaction of ethyl levulinate to γ-valerolactone in isopropanol solution under microwave irradiation. [4]BPh4 was revealed to be the best catalytic precursor, affording γ-valerolactone in 62% yield under optimized experimental conditions.

Graphical abstract: Ruthenium p-cymene complexes with α-diimine ligands as catalytic precursors for the transfer hydrogenation of ethyl levulinate to γ-valerolactone

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Article information


Submitted
17 Jul 2018
Accepted
18 Sep 2018
First published
19 Sep 2018

New J. Chem., 2018,42, 17574-17586
Article type
Paper

Ruthenium p-cymene complexes with α-diimine ligands as catalytic precursors for the transfer hydrogenation of ethyl levulinate to γ-valerolactone

L. Biancalana, S. Fulignati, C. Antonetti, S. Zacchini, G. Provinciali, G. Pampaloni, A. M. Raspolli Galletti and F. Marchetti, New J. Chem., 2018, 42, 17574
DOI: 10.1039/C8NJ03569E

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