50727-94-1Relevant articles and documents
Oxidovanadium(IV) complexes of 3-hydroxy-4-pyrone and 3-hydroxy-4- pyridinone ligands: A new generation of homogeneous catalysts for the epoxidation of geraniol
Pereira, Clara,Leite, Andreia,Nunes, Ana,Rebelo, Susana L. H.,Rangel, Maria,Freire, Cristina
, p. 98 - 104 (2010)
A novel generation of homogeneous catalysts for the epoxidation of geraniol, in the presence of tert-butyl hydroperoxide oxidant is reported. Oxidovanadium(IV) complexes of 3-hydroxy-4-pyrone and 3-hydroxy-4-pyridinone ligands exhibit excellent activity and selectivity towards the 2,3-epoxygeraniol product, only differing in the reaction times and turnover frequencies. The pyrone based complexes are the most efficient catalysts showing performances similar to that of the well known oxidovanadium(IV) acetylacetonate catalyst. Graphical abstract: [Figure not available: see fulltext.]
Photo-Oxidation of 2-(2-Furyl)-1,3-Dicarbonyl Compounds
Antonioletti, R.,Bonadies, F.,Pesci, S.,Scettri, A.
, p. 3947 - 3948 (1992)
A very efficient photo-sensitized oxidation of 2-(2-furyl)-1,3-dicarbonyl compounds 1 afford directly hydroperoxides 2 in stereoselective way.Compounds 2, easily isolated, can be conveniently employed in a selective epoxidation of trisubstituted allylic alcohols by a Sharpless-type procedure.
Klein,E. et al.
, p. 2025 - 2035 (1964)
Opposite Regioselectivity in the Epoxidation of Geraniol and Linalool with Molybdenum and Tungsten Peroxo Complexes
Arcoria, Antonino,Ballistreri, Francesco Paolo,Tomaselli, Gaetano Andrea,Furia, Fulvio Di,Modene, Giorgio
, p. 2374 - 2376 (1986)
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Total Synthesis of Kadcoccinic Acid A Trimethyl Ester
Gholami, Hadi,Trost, Barry M.,Zell, Daniel,Zhang, Guoting
supporting information, p. 12286 - 12293 (2021/08/20)
The first total synthesis of the trimethyl ester of kadcoccinic acid A is described. The central structural element of our synthesis is a cyclopentenone motif that allows the assembly of the natural product skeleton. A gold(I)-catalyzed cyclization of an enynyl acetate led to efficient construction of the cyclopentenone scaffold. In this step, optimization studies revealed that the stereochemistry of the enynyl acetate dictates regioisomeric cyclopentenone formation. The synthesis further highlights an efficient copper-mediated conjugate addition, merged with a gold(I)-catalyzed Conia-ene reaction to connect the two fragments, thereby forging the D-ring of the natural product. The synthetic strategy reported herein can provide a general platform to access the skeleton of other members of this family of natural products.
Transition Metal-Substituted Potassium Silicotungstate Salts as Catalysts for Oxidation of Terpene Alcohols with Hydrogen Peroxide
da Silva, Marcio Jose,da Silva Andrade, Pedro Henrique,Sampaio, Vinicius Fernando Coelho
, p. 2094 - 2106 (2020/11/13)
Abstract: In this work, the catalytic activity of the transition metal-substituted potassium silicotungstate salts (i.e. K8-nSiMn+W11O39 (Mn+ = Cu2+, Co2+, Ni2+, Zn2+ and Fe3+) was investigated on the oxidation reactions of the terpene alcohols with H2O2 aqueous solution. The metal-substituted silicotungstate salts were easily synthesized in one-pot reactions of the precursor metal solutions (i.e. Na2WO4, Na2SiO3 and MCln) with KCl added in stoichiometric amount; after this precipitation step, the solid heteropoly salts were filtered and dried in an oven. This procedure of synthesis avoids multi-step processes that starts from the pristine heteropolyacid. The substituted metal heteropoly salts were characterized by infrared spectroscopy, measurements of the specific surface area (BET) and porosimetry by isotherms of adsorption/desorption of N2, X-rays diffraction, thermal analyses, dispersive X-rays spectroscopy, scanning electronic microscopy. The acidity strength was estimated by potentiometric titration with n-butylamine. All the salts were evaluated as catalysts in terpenic alcohols oxidation reactions with H2O2. The K5SiFeW11O39 was the most active and selective catalyst toward oxidation products. The impacts of the main reaction variables such as catalyst concentration, temperature, oxidant load, and nature of the terpene substrate were assessed. The highest activity of the K5SiFeW11O39 catalyst was assigned to the highest Lewis acidity. Graphic Abstract: [Figure not available: see fulltext.].
Vanadium-doped sodium phosphomolybdate salts as catalysts in the terpene alcohols oxidation with hydrogen peroxide
Ferreira, Sukarno Olavo,Rodrigues, Alana Alves,Vilanculo, Castelo Bandane,da Silva, Márcio José,da Silva, Rene Chagas
, p. 24072 - 24085 (2021/07/29)
In this work, we have explored the catalytic activity of Keggin-type heteropolyanions PMo12?nVnO40(3+n)?(n= 0, 1, 2, or 3) in the form of sodium salts in green oxidation routes of terpene alcohols with hydrogen peroxide. Nerol was the model molecule selected to assess the impacts of the main reaction parameters, such as temperature, catalyst load, and stoichiometry of reactants. The impacts of the presence of vanadium at different proportions (i.e., V1, V2, and V3loads/per anion) in the structure of phosphomolybdate catalysts were assessed. All the catalysts were characterized by various techniques such as powder X-ray diffraction, attenuated diffuse reflectance infrared spectroscopy, ultraviolet-visible spectroscopy, thermogravimetric analysis, isotherms of adsorption-desorption of N2measurements of surface area, scanning electronic microscopy, energy-dispersive X-ray spectroscopy, andn-butylamine potentiometric titration. Among the catalysts assessed, Na4PMo11VO40was the most active and selective toward epoxides. The efficiency of this catalyst in the epoxidation of different terpene alcohols was investigated. Special attention was dedicated to correlating the composition and properties of the vanadium-doped phosphomolybdic catalysts with their catalytic activity.
