Issue 2, 2011
From the journal:

Green Chemistry

Cyclopentadienyl and pentamethylcyclopentadienyl ruthenium complexes as catalysts for the total deoxygenation of 1,2-hexanediol and glycerol†

Michelle E. Thibault,a   Domenico V. DiMondo,a   Michael Jennings,b   Patrícia Verardi Abdelnur,c   Marcos N. Eberlinc  and  Marcel Schlaf*a  

* Corresponding authors

a The Guelph-Waterloo Centre for Graduate Work in Chemistry (GWC)2 Department of Chemistry, University of Guelph, Guelph, Canada
E-mail: mschlaf@uoguelph.ca

b 185 Chelsea Avenue, London, ON
E-mail: mjennings@teksavvy.com

c ThoMSon Mass Spectrometry Laboratory Institute of Chemistry University of Campinas ñ UNICAMP, Campinas, SP Brazil
E-mail: eberlin@iqm.unicamp.br

Abstract

The ruthenium aqua complexes [cp*Ru(OH2)(N–N)](OTf) (cp* = η5-pentamethylcyclopentadienyl, N–N = 2,2′-bipyridine, phen = 1,10-phenanthroline, OTf− = trifluoromethanesulfonate) and the acetonitrile complex [cpRu(CH3CN)(bipy)](OTf) (cp = η5-cyclopentadienyl) are water-, acid-, and thermally stable (>200 °C) catalysts for the hydrogenation of aldehydes and ketones in sulfolane solution. In the presence of HOTf as a co-catalyst, they effect the deoxygenation of 1,2-hexanediol to 1-hexanol and hexane. Glycerol is deoxygenated to 1-propanol in up to 18% yield and under more forcing conditions completely deoxygenated to propene. The structure of the acetonitrile pro-catalyst [cpRu(CH3CN)(bipy)](OTf) has been determined by X-ray crystallography (space groupP[1 with combining macron] (a = 9.3778(10) Å; b = 10.7852(10) Å; c = 11.1818(13) Å; α = 101.718(5)°; β = 114.717(4)°; γ = 102.712(5)°; R = 3.95%).

Graphical abstract: Cyclopentadienyl and pentamethylcyclopentadienyl ruthenium complexes as catalysts for the total deoxygenation of 1,2-hexanediol and glycerol

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Article information

DOI
https://doi.org/10.1039/C0GC00255K
Article type
Paper
Submitted
23 Jun 2010
Accepted
02 Dec 2010
First published
24 Dec 2010

Green Chem., 2011,13, 357-366

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Cyclopentadienyl and pentamethylcyclopentadienyl ruthenium complexes as catalysts for the total deoxygenation of 1,2-hexanediol and glycerol

M. E. Thibault, D. V. DiMondo, M. Jennings, P. V. Abdelnur, M. N. Eberlin and M. Schlaf, Green Chem., 2011, 13, 357 DOI: 10.1039/C0GC00255K

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