Green Catalytic Baeyer–Villiger Oxidation with Hydrogen Peroxide in Water Mediated by PtII Catalysts

  title={Green Catalytic Baeyer–Villiger Oxidation with Hydrogen Peroxide in Water Mediated by PtII Catalysts},
  author={Alessandra Cavarzan and Alessandro Scarso and Paolo Sgarbossa and Rino A. Michelin and Giorgio Strukul},
Baeyer–Villiger oxidation of cyclic ketones with 35 % hydrogen peroxide as a green oxidant mediated by monomeric PtII complexes bearing alkyl diphosphines greatly benefits from the employment of water with anionic surfactants as reaction medium. Under such conditions, the reaction shows enhanced catalytic activity compared to that with organic solvents. For more acid sensitive substrates, hydrolysis of the lactone product to the corresponding hydroxy acid occurs. Mild experimental conditions… Expand
16 Citations
Baeyer–Villiger Oxidation of Cyclic Ketones Using Aqueous Hydrogen Peroxide Catalyzed by Potassium Salts of Tungstophosphoric Acid
The salts of 12-tungstophosphoric acid catalysts are prepared with varying potassium content. The resulting catalysts are active for the Baeyer–Villiger oxidation of cyclic ketones with 30 wt % H2O...
Room temperature Baeyer–Villiger oxidation using molecular oxygen over mesoporous zirconium phosphate
Lactones have found wide applications as key molecules for the synthesis of important bioactive compounds, natural products and polymers; and represent a valuable family of synthons for variousExpand
Baeyer–Villiger oxidation of ketones catalysed by rhenium complexes bearing N- or oxo-ligands
Abstract Rhenium (I, III–V or VII) complexes bearing N -donor or oxo-ligands catalyse the Baeyer–Villiger oxidation of cyclic and linear ketones ( e.g. 2-methylcyclohexanone, 2-methylcyclopentanone,Expand
Nano silica boron sulfuric acid as a dual Brønsted/Lewis acid and a heterogeneous catalyst in Baeyer–Villiger oxidation of ketones with hydrogen peroxide
In this work, new applications of one solid acid, nano silica boron sulfuric acid (NSBSA) as a dual Brønsted/Lewis acid in Baeyer–Villiger (B–V) oxidation of ketones with hydrogen peroxide has beenExpand
Platinum(II) Diphosphinamine Complexes for the Efficient Hydration of Alkynes in Micellar Media
Highly active monomeric bis-cationic platinum(II) catalysts bearing small bite angle diphosphinamine [N,N-bis(diarylphosphino)amine] ‘PNP’ ligands efficiently catalyze Markovnikov hydration ofExpand
Hydroamination of Unactivated Alkenes Catalyzed by Novel Platinum(II) N-Heterocyclic Carbene Complexes
Cationic platinum(II) complexes with bi- or tridentate (pincer) functionalized NHC ligands were found to be catalytically active in the hydroamination of unactivated alkenes. In some cases, theExpand
Micelle catalysed conversion of ‘on water’ reactions into ‘in water’ one
Abstract Micellar mediated organic reactions are of immense importance for the conversion of ‘on water’ reaction into ‘in water’ type. To avoid the use of toxic, volatile organic solvents as reactionExpand
Aqueous microdroplets containing only ketones or aldehydes undergo Dakin and Baeyer–Villiger reactions† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c9sc05112k
The Dakin and Baeyer–Villiger oxidation reactions require addition of peroxides as oxidants and an acid or a base as a catalyst to complete the reaction. Expand
Fabrication of Fe3O4‐l‐dopa‐CuII/SnIV@Micro‐Mesoporous‐SiO2 Catalyst Applied to Baeyer–Villiger Oxidation Reaction
A Magnetic mFe3O4‐l‐dopa‐CuII/SnIV@micro‐mesoporous‐SiO2 catalyst was successfully prepared. The catalyst exhibits high and stable catalytic activity for the Baeyer–Villiger oxidation reaction withExpand
Recent advances in catalysis in micellar media
The present review paper deals with the development of catalytic systems in water in the presence of micelles obtained by addition of surfactants, focusing on the effects of these simple, economic,Expand


Transition Metal Catalysis in the Baeyer-Villiger Oxidation of Ketones.
  • G. Strukul
  • Chemistry, Medicine
  • Angewandte Chemie
  • 1998
Environmentally friendly oxidizing agents such as hydrogen peroxide or dioxygen can be used today in catalytic versions of the almost one century old Baeyer-Villiger oxidation with transition metalExpand
Asymmetric Sulfoxidation of Thioethers with Hydrogen Peroxide in Water Mediated by Platinum Chiral Catalyst
Easy stereoselective oxidation of prochiral aryl alkyl sulfides 2 to the corresponding sulfoxides can be achieved in water-surfactant medium with inexpensive hydrogen peroxide mediated by the chiralExpand
Catalytic asymmetric Baeyer-Villiger oxidation in water by using Pt(II) catalysts and hydrogen peroxide: supramolecular control of enantioselectivity.
The asymmetric Baeyer-Villiger oxidation in water catalyzed by 1 a-h in the presence of micelles is a viable reaction that often benefits from the hydrophobic effect, leading to substantial increases in enantioselectivity. Expand
Mild catalytic oxidation of secondary and tertiary amines to nitrones and N-oxides with H2O2 mediated by Pt(II) catalysts
Bridging hydroxo complexes of Pt(II) can be used as catalysts for the oxidation of tertiary and secondary amines under mild conditions using the environmentally benign hydrogen peroxide as theExpand
Baeyer-Villiger oxidation of ketones by peroxomolybdenum complexes: A revisit
Abstract The Baeyer-Villiger oxidation of cyclopentanone to δ-valerolactone by a peroxomolybdenum complex, MoO(O) 2 (dipic), under catalytic (hydrogen peroxide) conditions was reported in theExpand
New (old) hydroxo complexes of platinum(II) as catalysts for the Baeyer-Villiger oxidation of ketones with hydrogen peroxide
Enantioselective Baeyer-Villiger oxidation of cyclic ketones with hydrogen peroxide can be obtained using (P-P * )Pt(2-van) complexes (P-P * , chiral diphosphine; 2-van, bis-anion of 2-vanillin) asExpand
Cationic Co(III)(salen)-catalyzed enantioselective Baeyer-Villiger oxidation of 3-arylcyclobutanones using hydrogen peroxide as a terminal oxidant
A cationic Co(III)(salen) complex of cis-β-structure was found to serve as an efficient catalyst for asymmetric Baeyer–Villiger reaction of 3-substituted cyclobutanone using hydrogen peroxide as aExpand
Toward green catalytic synthesis—Transition metal-catalyzed reactions in non-conventional media
Abstract Solvents play a critical role in “greening” synthetic chemistry, and this is also true in catalytic organic synthesis. This review attempts to summarize the progress made in the past a fewExpand
Oxidation of cyclic ketones by hydrogen peroxide catalysed by Group 6 metal peroxo complexes
Molybdenum peroxo complexes stabilized by picolinato and pyridine 2,6-dicarboxylato ligands catalyse oxidation of cyclic ketones by H2O2 to lactones and their derivatives; this represents a catalyticExpand
Baeyer-Villiger oxidation of cyclic ketones with hydrogen peroxide catalyzed by cationic complexes of platinum(II): selectivity properties and mechanistic studies
The catalytic oxidation of simple cyclic ketones with hydrogen peroxide to give the corresponding lactones is reported. The reaction is catalyzed by complexes of Pt(II) of the type [(P-P)Pt(CF[subExpand