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ChemSusChem

Title:		Catalytic deoxydehydration of diols to olefins by using a bulky cyclopentadiene-based trioxorhenium catalyst
Author(s):		Raju S; Jastrzebski JT; Lutz M; Klein Gebbink RJ;
Address:		"Organic Chemistry & Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, Universiteitsweg 99, 3584 CG Utrecht (The Netherlands)"
Journal Title:		ChemSusChem
Year:		2013
Volume:		20130710
Issue:		9
Page Number:		1673 - 1680
DOI:		10.1002/cssc.201300364
ISSN/ISBN:		1864-564X (Electronic) 1864-5631 (Linking)
Abstract:		"A bulky cyclopentadienyl (Cp)-based trioxorhenium compound was developed for the catalytic deoxydehydration of vicinal diols to olefins. The 1,2,4-tri(tert-butyl)cyclopentadienyl trioxorhenium (2) catalyst was synthesised in a two-step synthesis procedure. Dirhenium decacarbonyl was converted into 1,2,4-tri(tert-butyl)cyclopentadienyl tricarbonyl rhenium, followed by a biphasic oxidation with H2 O2 . These two new three-legged compounds with a 'piano-stool' configuration were fully characterised, including their single crystal X-ray structures. Deoxydehydration reaction conditions were optimised by using 2 mol % loading of 2 for the conversion of 1,2-octanediol into 1-octene. Different phosphine-based and other, more conventional, reductants were tested in combination with 2. Under optimised conditions, a variety of vicinal diols (aromatic and aliphatic, internal and terminal) were converted into olefins in good to excellent yields, and with minimal olefin isomerisation. A high turnover number of 1400 per Re was achieved for the deoxydehydration of 1,2-octanediol. Furthermore, the biomass-derived polyols (glycerol and erythritol) were converted into their corresponding olefinic products by 2 as the catalyst"
Keywords:		Alkenes/*chemistry Catalysis Cyclopentanes/*chemistry Glycols/*chemistry Oxygen/*chemistry Rhenium/*chemistry Volatilization biomass cyclopentadienyl ligands deoxydehydration homogeneous catalysis rhenium;
Notes:		"MedlineRaju, Suresh Jastrzebski, Johann T B H Lutz, Martin Klein Gebbink, Robertus J M eng Research Support, Non-U.S. Gov't Germany 2013/07/12 ChemSusChem. 2013 Sep; 6(9):1673-80. doi: 10.1002/cssc.201300364. Epub 2013 Jul 10"