Triethylborane Induced Perfluoroalkylation of Silyl Enol Ethers and Ketene Silyl Acetals with Perfluoroalkyl Iodides.
スポンサーリンク
概要
- 論文の詳細を見る
Reaction of perfluoroalkyl iodides with silyl enol ethers mediated by Et<SUB>3</SUB>B in the presence of base such as 2,6-dimethylpyridine provides mixtures of perfluoroalkylated trialkylsilyl enol ethers and α-perfluoroalkylated ketones. The yield and distribution of the products heavily depend on the nature of base employed. Treatment of a reaction mixture consisting of perfluoroalkylated silyl enol ether and α-perfluoroalkylated ketone with coned HCl in THF gives α-perfluoroalkylated ketone as a single product. Reaction of ketene silyl acetals with perfluoroalkyl iodides in the absence of base affords α-perfluoroalkylated esters in excellent yields.
- 公益社団法人 日本化学会の論文
著者
-
Miura Katsukiyo
Department Of Applied Chemistry Graduate School Of Science And Engineering Saitama University
-
Utimoto Kiitiro
Department Of Industrial Chemistry Faculty Of Engineering Kyoto University
-
Takeyama Yoshihiro
Department of Industrial Chemistry, Faculty of Engineering, Kyoto University
-
Oshima Koichiro
Department of Chemistry, Massachusetts Institute of Technology
関連論文
- Asynchronous (heterochronic) bilateral renal infarction associated with primary antiphospholipid syndrome
- Renal arteriovenous malformation with thrombus in the inferior vena cava
- Copper-Catalyzed Arylation of Chlorosilanes with Grignard Reagents
- Palladium-catalyzed Mizoroki-Heck Reactions of 2-Methylene-1,3-dithiane 1-Oxide with Aryl Iodides
- Synthesis of β,γ-Unsaturated Ketones from Acid Chlorides through Carbon-Pentamethylcyclopentadienyl Bond Formation and Cleavage
- Synthesis of Prenylarenes and Related (Multisubstituted Allyl)arenes from Aryl Halides and Homoallyl Alcohols via Palladium-Catalyzed Retro-Allylation
- Manganese-catalyzed Phenylation of Acetylenic Compounds with a Phenyl Grignard Reagent
- Preparation of Deuterium Labelled Organophosphonium Salts (Wittig Salts) under Hydrothermal Condition Catalyzed by Molecular Sieves
- Trialkylmanganate Mediated Radical Addition of Triphenylgermane to Carbon-Carbon Multiple Bonds
- Ruthenium-catalyzed Isomerization of Alkenol into Alkanone in Water under Irradiation of Microwaves
- Radical Addition of α-Halo Ester to Homoallylic Gallium or Indium Species : Formation of Cyclopropane Derivatives
- Allylation of Carbonyl Compounds with Allylic Gallium Reagents
- Preparation of Organoytterbium Reagent from Ytterbium Trichloride and Organomagnesium
- Intramolecular Carbostannylation of Allyl- and Vinylstannanes via a Radical Chain Process
- Hydroxy Group-Directed Homolytic Hydrostannylation of Alkenols with Dibutylchlorostannane
- Stereoselective Allylation of 3-Oxo Amides
- 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
- Indium(III)-catalyzed Coupling between Alkynes and Aldehydes to α,β-Unsaturated Ketones
- Particle Content of the ($k$, 3)-Configurations
- Fermionic Formulas for ($k$, 3)-admissible Configurations
- Platinum(II)-catalyzed Annulation of 5-Methyl-5-hexen-1-ols with Aldehydes
- S_N2 Type Hydrolysis of Secondary Alkyl Halides and Sulfonates in Hydrothermal Water
- Platinum(II)-catalyzed Acetal-Ene Reaction : Easy Access to Homoallylic Ethers
- Efficient Alkenation of Aldehydes and Ketones to α,β-Unsaturated Esters Using α,α-Bis(dimethylsilyl)-substituted Esters
- Synthesis of Coordinatively Unsaturated Cobalt(II)-Alkyl Complexes Bearing Phosphorus-bridged [1.1]Ferrocenophanes
- Facile Preparation of Vicinal Allylsiloxy-and Vinylsiloxyhaloalkanes and Their Radical Cyclization Reaction
- 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
- Radical Addition of Polyhaloalkanes to 2-Ethynyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
- Radical Addition of Alkyl Halides to 2-Methylene-1,3-dithiane Monoxide as a Ketene Equivalent
- Extended Pummerer Reaction of Arylketene Dithioacetal Monoxides with Aromatic Compounds by Means Trifluoromethanesulfonic Anhydride
- Triethylborane-Induced Radical Reaction of Alkynylgallium with α-Halo Carbonyl Compounds
- Triethylborane Induced Radical Reaction of Gallium Enolates with α-Halo Esters
- 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
- Fabrication of Nano-structure by Diels-Alder Reaction
- Synthesis of Pyrimidines via Base-induced Condensation of α-Chloro Oxime Derivatives
- Cobalt-catalyzed Cross-coupling Reactions of Aryl Bromides with Alkyl Grignard Reagents
- Regio- and Stereoselective Additions of Diphenyldithiophosphinic Acid to N-(1-Alkynyl)amides and 1-Alkynyl Sulfides
- Silylcupration and Copper-Catalyzed Carbomagnesiation of Ynamides : Application to Aza-Claisen Rearrangement
- Regio- and Stereoselective Hydrothiolation Reactions of Ynamides with Diphenyldithiophosphinic Acid : Straightforward Synthesis of Ketene N,S-Acetal Derivatives
- Transformations of N-Allyl-N-(phenylethynyl)arenesulfonamides into 2,2-Disubstituted 4-Pentenenitriles through Aza-Claisen Rearrangement that Follows Carbomagnesiation
- Cobalt-Catalyzed Allylzincations of Internal Alkynes
- Acid-Catalyzed Cyclization of Vinylsilanes Bearing a Hemiacetal Group^1
- New Access to Cross-Coupling Reaction between Arylsilanes or Heteroarylsilanes and Aryl Halides Mediated by a Copper(I)Salt^1
- Introduction of Electrophiles to the α-Position of α,β-Unsaturated Aldehydes and Ketones by Sequential Conjugate Aminosilylation-Alkylation-Deamination
- Development of New Reagents Containing Silicon and Related Metals and Application to Practical Organic Syntheses
- Rhodium-Catalyzed Reaction of 1-Alkynylphosphines with Water Yielding (E)-1-Alkenylphosphine Oxides
- Atom-transfer Radical Addition of α-Iodo Esters to 1-Alkynyl Sulfides
- Palladium-Catalyzed 1-Methylene-2-propenylation Reactions of Aryl Bromides with 3,4-Alkadien-1-ols via Carbon-Carbon Bond Cleavage for the Synthesis of 2-Aryl-1,3-butadiene Derivatives
- Efficient Aerobic Oxidation of Phosphines, Phosphites, and Sulfides by Using Trialkylborane
- Nickel-catalyzed Carbometalation Reactions of [2-(1-Propynyl)phenyl]methanol with 1-Alkenylmagnesium Reagents
- Cobalt-catalyzed Cross-coupling Reaction of Chloropyridines with Grignard Reagents
- Radical Addition of 2-Iodoalkanamide or 2-Iodoalkanoic Acid to Alkenes with a Water-Soluble Radical Initiator Initiator in Aqueous Media: Facile Synthesis of γ-Lactones
- Reduction of Organic Halides with Tri-2-furylgermane: Stoichiometric and Catalytic Reduction
- Radical Cyclization of N-Allyl-2-halo Amide in Water
- Three-step α-Acylation of (E)-Cinnamate Esters with Inversion of Stereochemistry through Formation and Cleavage of Carbon-Pentamethylcyclopentadienyl Bonds
- Stereoselective Reduction of α,β-Epoxy Ketones into erythro-α,β-Epoxy Alcohols with Sodium Borohydride in the Presence of Calcium Chloride
- Tandem Aldol-Reduction Reaction of Dimethylsilyl Enolates:A New Method for Stereoselective Preparation of 1, 3-Diols
- Reaction of Tantalum-Alkyne Complexes with Hydrazones. Stereoselective Synthesis of (E)-Allylic Hydrazines.
- Methylenation of Esters with Bis(iodozincio)methane-TiCl_2-TMEDA System
- A Facile Synthesis of 1,1-Disilylethenes via Me_3MgLi-Induced Monomethylation of Dibromodisilylmethanes
- Bis(cyclopentadienyldicarbonyliron) as a Convenient Carbon Monoxide Source in Palladium-catalyzed Carbonylative Coupling of Aryl Iodides with Amines, Alcohols, and Thiols
- Pivotal role of epithelial cell adhesion molecule in the survival of lung cancer cells
- 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.
- 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
- 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.
- Palladium catalyzed hydrostannylation and hydrogermylation of acetylenes.
- Hydrostannation and hydrogermylation of allenes.
- Measurements of double differential neutron emission cross sections for fusion reactor candidate elements.
- Stereochemical studies on the nucleophilic substitution in the reaction of allylic phosphates with organoaluminum reagents.
- An efficient route to both enantiomers of N-(p-tolylsulfonyl)benzenesulfonimidamide and their use for asymmetric allylic amination of olefins.
- 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 Reaction of O,O′-Diethyl α-Lithiomethylphosphonate with Organic Dihalides
- 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.
- 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.
- Cr(III) or Ce(IV) impregnated perfluorinated resin-sulfonic acid catalyst for the oxidation of alcohols.
- 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