Chromium(VI) or ruthenium(II) complex catalysis in oxidation of alcohols to aldehydes and ketones by means of bis(trimethylsilyl) peroxide.

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概要

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• Bis(trimethylsilyl) peroxide (BTSP) serves as an effective oxidant of alcohols in the presence of chromium(VI) or ruthenium(II) complexes as catalysts in dichloromethane. Selective oxidation of primary alcohols in preference to secondary ones using RuCl<SUB>2</SUB>(PPh<SUB>3</SUB>)<SUB>3</SUB> as a catalyst is also described.

• 公益社団法人 日本化学会の論文

著者

• Takai Kazuhiko

  Department Of Applied Chemistry Faculty Of Engineering Okayama University

• Utimoto Kiitiro

  Department Of Industrial Chemistry Faculty Of Engineering Kyoto University

• Nozaki Hitosi

  Department of Industrial Chemistry, Faculty of Engineering Kyoto University

• Matsubara Seijiro

  Department of Industrial Chemistry, Faculty of Engineering Kyoto University

• Oshima Koichiro

  Department of Chemistry, Massachusetts Institute of Technology

• Kanemoto Shigekazu

  Department of Industrial Chemistry, Faculty of Engineering, Kyoto University

関連論文

• Fullerene and Sulfur Compounds
• Improved Synthesis and Crystal Structure of TiCl_3 (tmeda) (thf): A Highly Stereoselective Pinacol Coupling Reagent for Aromatic Aldehydes
• Preparation of Deuterium Labelled Organophosphonium Salts (Wittig Salts) under Hydrothermal Condition Catalyzed by Molecular Sieves
• Ruthenium-catalyzed Isomerization of Alkenol into Alkanone in Water under Irradiation of Microwaves
• Allylation of Carbonyl Compounds with Allylic Gallium Reagents
• Carbazole Synthesis by Platinum-catalyzed C-H Functionalizing Reaction Using Water as Reoxidizing Reagent
• Preparation of Organoytterbium Reagent from Ytterbium Trichloride and Organomagnesium
• Stereoselective Allylation of 3-Oxo Amides
• Preparation of Ester-group Substituted Allylic Zinc by Palladium-catalyzed Umpolung of γ-Acyloxy-α,β-unsaturated Ester by Bis(iodozincio)methane
• Nickel-catalyzed [4+2] Cycloaddition of Alkynes to Carbonylsalicylamides via Elimination of Isocyanates
• Ruthenium Catalyzed Deuterium Labelling of α-Carbon in Primary Alcohol and Primary/Secondary Amine in D_2O
• Palladium-Catalyzed H-D Exchange Reaction under Hydrothermal Condition
• S_N2 Type Hydrolysis of Secondary Alkyl Halides and Sulfonates in Hydrothermal Water
• Preparation and Reaction of Phenylsulfonyl-substituted Dizinciomethane
• Facile Preparation of Vicinal Allylsiloxy-and Vinylsiloxyhaloalkanes and Their Radical Cyclization Reaction
• Selective Cyclotrimerization of Acetylenes via Tantalum-Alkyne Complexes
• Alkylidenation of Ketones by gem-Dibromoalkane, SmI_2, and Sm in the Presence of Catalytic Amount of CrCl_3
• Ytterbium Catalyzed Oxidation of Alcohols to Aldehydes and Ketones by Means of Iodosylbenzene
• Tris(trimethylsilyl)silyl Radical Induced Bicyclization of 1,6-Dienes and 1,6-Enynes Providing 3,3-Bis(trimethylsilyl)-3-silabicyclo[3.3.0]octanes and 3-Silabicyclo[3.3.0]oct-1-enes
• Stereocontrolled Reduction of 2-Acyl-1,3-oxathiane Derivatives by Zn(BH_4)_2 and YCl_3-NaBH_4
• 2-Lithio-2-trimethylsilyl-1-silacyclopentane as a Synthetic Equivalent of 1-Lithio-1,4-butanediol
• Sequential Introduction of Carbon Nucleophiles onto Silicon Atoms Using Methyl as a Leaving Group
• Samarium Diiodide-Mediated Reaction of Organic Halides with Carbonyl Compounds
• A Preparation of β-Oxoester Enolate Equivalents from SmI_2 and α-Bromoalkanoates
• Preparation of Dialkoxyborylbis(bromozincio)methane and Its Reaction with Electrophiles
• Wittig Type Methylenation of Ketones with Bis(iodozincio)methane and Ionic Liquid
• The Rate Enhancement Effect of Protodesilylation of Arylsilane Derivatives
• Iron(II) Chloride-mediated Addition of Dialkylmagnesium to Carbonyl Compounds
• Fabrication of Nano-structure by Diels-Alder Reaction
• Stereoselective Reduction of α,β-Epoxy Ketones into erythro-α,β-Epoxy Alcohols with Sodium Borohydride in the Presence of Calcium Chloride
• Nickel-catalyzed Decarbonylative Cycloaddition of Phthalic Anhydrides with 1,3-Dienes
• Wittig Like Methylenation of Aldehydes in a Microflow System: Selective Methylenation by Differential of Plural Reactions
• Reaction of Tantalum-Alkyne Complexes with Hydrazones. Stereoselective Synthesis of (E)-Allylic Hydrazines.
• Methylenation of Esters with Bis(iodozincio)methane-TiCl_2-TMEDA System
• Catalytic Performance of Tantalum-η^2-Alkyne Complexes [TaCl_3(R^1C≡CR^2)L_2] for Alkyne Cyclotrimerization
• Successive Carbon-Carbon Bond Formation by Sequential Generation of Radical and Anionic Species with Manganese and Catalytic Amounts of PbCl_2 and Me_3 SiCl
• Nucleophilic addition of organochromium reagents to carbonyl compounds
• Transformation of Aldehydes into (E)-1-Alkenylsilanes and (E)-1-Alkenylboronic Esters with a Catalytic Amount of a Chromium Salt
• Nickel-catalyzed Cycloaddition of Aromatic (O-Benzyl)ketoximes with Alkynes to Produce Isoquinoline and Isoquinoline N-Oxide Derivatives
• Nickel-catalyzed Heteroannulation of o-Haloanilines with Alkynes
• Teritary Amine-Accelerated Allylgallation of Terminal Alkynes
• Activation of Manganese Metal with a Catalytic Amount of Lead and Me_3SiCl and Its Application to Organic Synthesis
• Nickel-catalyzed Decarboxylative Polymerization of 6-Alkynylisatoic Anhydride
• Structure of a cumulene bearing bulky substituents. X-ray study of 1,1,4,4-terakis(trimethylsilyl)butatriene.
• Triethylborane-induced hydrodehalogenation of organic halides by tin hydrides.
• Palladium Catalyzed Reaction of Silacyclobutanes with Acetylenes.
• Et3B induced stereoselective radical addition of Ph3GeH to carbon-carbon multiple bonds and its application to isomerization of olefins.
• Thiocarbonyl Ylides. Attempted Preparation and Related Reactions
• Preparative and Structural Studies of Kostanecki's Compound
• The Reduction of gem-Dibromocyclopropanes by Means of Chromium(II) Acetate or Potassium Pentacyanocobaltate
• Regiocontrolled formation of 4,5-dihydro-3(2H)-furanones from 2-butyne-1,4-diol derivatives. Synthesis of bullatenone and geiparvarin.
• Highly selective carbon-carbon bond forming reactions mediated by chromium(II) reagents.
• Cross-coupling reaction between enol phosphates and organoaluminium compounds in the presence of palladium(0) catalyst.
• The Reaction of Styryl Sulfoxides or Sulfones with Boranes
• Reaction of organoaluminium reagents with cyclopropylmethyl acetates and 2-vinylcyclopropane-1,1-dicarboxylate esters.
• 1-Bromo-2-ethoxycyclopropyllithium: A synthetic equivalent of 2-lithio- or 3-lithiopropenal. Application to the synthesis of juvenile hormone (JH-II), .BETA.-sinensal, and jasmonoids.
• A novel synthesis of .ALPHA.-methylene-.GAMMA.-butyrolactones.
• Isomerization of allylic alcohols catalyzed by vanadium or molybdenum complexes.
• Reformatsky type reaction with new aluminium reagents containing Al-Sn or Al-Pb linkage.
• New methods for the synthesis of 3(2H)-furanones and 2(5H)-furanones.
• Alkylation of bromocyclopropanes and bromoarenes by means of dibutylcopperlithium and alkyl halides.
• A facile ring enlargement reaction via .BETA.-oxido carbenoid.
• The Reaction of Ethyl Azidoformate with Electron Deficient Olefins and the Thermal Ring Opening of the Resulting Aziridines.
• The Photolysis and Thermolysis of Ethyl Azidoformate in the Presence of Ketones
• A practical synthesis of polyhalomethyllithium-carbonyl adducts.
• Abnormal nazarov reaction. A new synthetic approach to 2,3-disubstituted 2-cyclopentenones.
• Tungsten hexachloride-catalyzed decomposition of diazo compounds. A novel oxazole synthesis.
• Palladium catalyzed hydrostannylation and hydrogermylation of acetylenes.
• Hydrostannation and hydrogermylation of allenes.
• Condensation Reactions of Sulfonylcarbanion
• Synthesis and Reactions of Sulfonium Diacylmethylide Having Active Hydrogen
• Intramolecular cyclization of nerol and the related attack of (Z)-allylic alcohol moiety on the terminal olefin linkage as induced by TiCl4-PhNHMe complex. Synthesis of nezukone.
• The Nucleophilic Cyclopropylation of the Condensed Aromatic Ring with Sulf onylcarbanion
• Stereochemical studies on the nucleophilic substitution in the reaction of allylic phosphates with organoaluminum reagents.
• Synthesis of [9]Heterophanes from 2-Cyclododecenone
• Carbocyclic ring formation by the intramolecular reaction between enol silyl ether and allylic acetate moieties.
• One-pot synthesis of tetrahydrofuran derivatives from allylic alcohols and vinyl ethers by means of palladium(II) acetate.
• Synthesis of homoallylic alcohols from allylic phosphates and aldehydes with organoaluminum reagent containing Al-Sn linkage.
• The 1-Methylene Derivatives of [7](2,6)Pyridinophane. Preparative and Conformational Studies
• The Absolute Configurations of 2-Phenylaziridine and Its Derivatives
• Thermolysis and Photolysis of Benzopinacol Dicarboxylates
• The Reaction of O,O′-Diethyl α-Lithiomethylphosphonate with Organic Dihalides
• The Oxidation of Alkylbenzenes and Acylcarbinols by Means of Benzopinacol Diesters
• Cyclopentenone synthesis from 1,1-dichloroallyllithium-ketone adducts as well as from dichlorocarbene-allyl alcohol adducts.
• The Dehalogenation of Organic Halides by Means of Iron(II) Chloride in Dimethyl Sulfoxide
• Triethylborane Induced Perfluoroalkylation of Silyl Enol Ethers and Ketene Silyl Acetals with Perfluoroalkyl Iodides.
• Rearrangement of vic-diol monoacetates promoted by organoaluminium compounds.
• Stereoselective epoxidation of allylic alcohols and dehydrogenative oxidation of secondary alcohols by means of t-butyl hydroperoxide and aluminium reagents.
• Baeyer-Villiger oxidation with Me3SiOOSiMe3 under assistance of SnCl4 or BF3OEt2.
• Chromium(VI) or ruthenium(II) complex catalysis in oxidation of alcohols to aldehydes and ketones by means of bis(trimethylsilyl) peroxide.
• Aliphatic Claisen rearrangement promoted by organoaluminium reagents.
• The Syntheses and Reactions of Sulfenyl-substituted Sulfonium Ylides
• The Acid-Catalyzed Ring-Opening of Cyclooctenimine Derivatives
• Cr(III) or Ce(IV) impregnated perfluorinated resin-sulfonic acid catalyst for the oxidation of alcohols.
• A New Synthesis of Thiophenes
• Photoinduced Transannular Reaction of 4,5-Octamethylene-1,3-dioxolen-2-one
• The Reaction of Acyl-substituted Sulfonium and Pyridinium Ylides with Diphenylthiirene Dioxide
• Palladium-catalyzed ketone synthesis from acyl chloride and organoaluminum reagents.
• Preparation of 2-alkenylsilanes and 2-alkenylstannanes by the reaction of 2-alkenyl-1,1-cyclopropanedicarboxylate esters with PhMe2SiAlEt2 and (Ph3Sn)2Zn. Generation of 2-alkenyl-3-cyclopentene-1,1-decarboxylates via alkenyl-substituted .PI.-allylpalladiu
• Photochemistry of Non-enolizable β-Diketones Containing Cyclopropane Ring in Conjugation

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