The use of tetraalkylammonium salts or imidazolium ionic liquids in catalytic oxidations of alcohols with tetra-N-propylammonium perruthenate allows recovery and reuse of the oxidant; this concept may find application in the recovery of other homogenous catalysts.
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Elucidating the mechanism of the Ley-Griffith (TPAP) alcohol oxidation.
Chem Sci
December 2017
School of Chemistry and Molecular Biosciences , University of Queensland, Brisbane 4072 , Queensland , Australia . Email: ; Email:
The Ley-Griffith reaction is utilized extensively in the selective oxidation of alcohols to aldehydes or ketones. The central catalyst is commercially available tetra--propylammonium perruthenate (TPAP, -PrN[RuO]) which is used in combination with the co-oxidant -methylmorpholine -oxide (NMO). Although this reaction has been employed for more than 30 years, the mechanism remains unknown.
View Article and Find Full Text PDFATP3 and MTP3: Easily Prepared Stable Perruthenate Salts for Oxidation Applications in Synthesis.
Chemistry
March 2018
School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072, Australia.
The Ley-Griffith tetra-n-propylammonium perruthenate (TPAP) catalyst has been widely deployed by the synthesis community, mainly for the oxidation of alcohols to aldehydes and ketones, but also for a variety of other synthetic transformations (e.g. diol cleavage, isomerizations, imine formation and heterocyclic synthesis).
View Article and Find Full Text PDFRole of Mediator and Effects of Temperature on ortho-C-N Bond Fusion Reactions of Aniline Using Ruthenium Templates: Isolation and Characterization of New Ruthenium Complexes of the in-Situ-Generated Ligands.
Inorg Chem
May 2017
Department of Inorganic Chemistry, Indian Association for the Cultivation of Science , Kolkata 700 032, India.
In this work, ortho-C-N bond fusion reactions of aniline are followed by the use of two different ruthenium mediators. Reaction of aniline with [Ru(terpy)Cl] (terpy = 2,2':6',2″-terpyridine) resulted in a trans bis-aniline ruthenium(II) complex [1] which upon oxidation with HO produced compound [2] of a bidentate ligand, N-phenyl-1,2-benzoquinonediimine, due to an oxidative ortho-C-N bond fusion reaction. Complex [1] and aniline (neat) at 185 °C produced a bis-chelated ruthenium complex (3).
View Article and Find Full Text PDFNMO⋅TPB: a selectivity variation on the Ley-Griffith TPAP oxidation.
Chemistry
February 2015
School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072 (Australia).
A non-hygroscopic tetraphenylborate salt of N-methylmorpholine-N-oxide (NMO) is reported (NMO⋅TPB), which modulates the standard Ley-Griffith oxidation such that benzylic and allylic alcohols are oxidised selectively. An attractive feature of this new protocol is that anhydrous conditions are not required for this selective tetra-n-propylammonium perruthenate (TPAP) oxidation, superseding the requirement of molecular sieves.
View Article and Find Full Text PDFThe grounds for the activity of TPAP in oxidation catalysis in supercritical carbon dioxide when confined in hybrid fluorinated silica matrices.
Phys Chem Chem Phys
April 2008
Centro de Química-Física Molecular, Instituto Superior Técnico, Complexo I, Av. Rovisco Pais 1, 1049-001, Lisboa, Portugal.
Fluorinated organo-silica gels doped with tetra-n-propylammonium perruthenate (TPAP) are excellent catalysts for the aerobic oxidative dehydrogenation of alcohols in supercritical CO2 (scCO2). Their activity and stability are subtly dictated by structure, depending on the degree of fluorination and on the length of the fluoroalkyl chain linked to the silica network. Such dependence reflects the hydrophilic-hydrophobic balance (HHB) of the matrix, as evaluated by diffuse reflectance infrared Fourier transform (DRIFT) spectroscopy.
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