- Synthetic method of difluoromethyl compound
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The invention discloses a synthetic method of a difluoromethyl compound. The synthetic method of the difluoromethyl compound comprises the following steps: selecting styrene derivatives as raw materials, selecting dichloromethane as a solvent and triethylamine trihydrofluoride as a fluorinating agent and carrying out sufficient reaction at the temperature of 70 to 90 DEG C in the presence of a hypervalent iodine reagent iodobenzene diacetate; after the reaction is ended, separating and purifying reaction liquid to obtain the difluoromethyl compound. The synthetic method disclosed by the invention has the advantages of reasonable process conditions, simple operation, short reaction time, stable conversion rate and yield and wide substrate range. By adopting the triethylamine trihydrofluoride as the fluorinating agent, convenience in treatment is realized and no metal catalyst is needed, so the synthetic method is a high-efficiency synthetic method for synthesizing the difluoromethyl.
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Paragraph 0041; 0042; 0043; 0044
(2017/09/29)
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- Geminal difluorination of α,α’- disubstituted styrenes using fluoro-benziodoxole reagent. Migration aptitude of the α-substituents
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α,α’-Disubstituted styrenes undergo a difluorination-rearrangement reaction with fluoro-benzoiodoxole reagent 1. The reaction is catalyzed by Pd(MeCN)4(BF4)2 and Cu(MeCN)4PF6. We have studied the rear
- Ilchenko, Nadia O.,Szabó, Kálmán J.
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p. 104 - 109
(2017/09/06)
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- Nickel-Catalyzed Difluoroalkylation of (Hetero)Arylborons with Unactivated 1-Bromo-1,1-difluoroalkanes
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A nickel-catalyzed cross-coupling between (hetero)arylborons and unactivated 1-bromo-1,1-difluoroalkanes has been developed. The use of two ligands (a bidentate bipyridine-based ligand, 4,4′-ditBu-bpy, and a monodentate pyridine-based ligand, DMAP) offers a highly efficient nickel-based catalytic system to prepare difluoroalkylated arenes which have important applications in medicinal chemistry. Ligand combo: The title reaction requires the use of a combined (2+1) ligand system, that is, a combination of a bi- and monodentate ligand (4,4′-ditBu-bpy + DMAP). This system allows employment of a wide range of unactivated 1-bromo-1,1-difluoroalkanes as coupling partners, thus providing a highly efficient method for applications in drug discovery and development. bpy=bipyridine, DMAP=4-(N,N-dimethylamino)pyridine.
- Xiao, Yu-Lan,Min, Qiao-Qiao,Xu, Chang,Wang, Ruo-Wen,Zhang, Xingang
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supporting information
p. 5837 - 5841
(2016/05/09)
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- Difluoroalkyl-substituted aryl or hetetoaryl compounds, and preparation method and application thereof
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The invention discloses difluoroalkyl-substituted aryl or hetetoaryl compounds, and a preparation method and application thereof. The preparation method comprises the following step: in a solvent, carrying out Suzuki coupling reaction disclosed in the spe
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Paragraph 0221-0223
(2016/10/10)
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- Hypervalent Iodine-Mediated Fluorination of Styrene Derivatives: Stoichiometric and Catalytic Transformation to 2,2-Difluoroethylarenes
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Fluorination of styrene derivatives with a reagent system composed of μ-oxo-bis[trifluoroacetato(phenyl)iodine] and a pyridine·HF complex gave the corresponding (2,2-difluoroethyl)arenes in good yields. Similarly, the reagent of PhI(OCOCF3)2 and the pyridine·HF complex acted as a fluorinating agent for styrene derivatives. The fluorination of styrene derivatives with the pyridine·HF complex underwent under catalytic conditions using 4-iodotoluene as a catalyst and m-CPBA as a terminal oxidant.
- Kitamura, Tsugio,Muta, Kensuke,Oyamada, Juzo
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p. 10431 - 10436
(2015/11/18)
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- Designer HF-Based fluorination reagent: Highly regioselective synthesis of fluoroalkenes and gem -difluoromethylene compounds from alkynes
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Hydrogen fluoride (HF) and selected nonbasic and weakly coordinating (toward cationic metal) hydrogen-bond acceptors (e.g., DMPU) can form stable complexes through hydrogen bonding. The DMPU/HF complex is a new nucleophilic fluorination reagent that has high acidity and is compatible with cationic metal catalysts. The gold-catalyzed mono- and dihydrofluorination of alkynes using the DMPU/HF complex yields synthetically important fluoroalkenes and gem-difluoromethlylene compounds regioselectively.
- Okoromoba, Otome E.,Han, Junbin,Hammond, Gerald B.,Xu, Bo
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supporting information
p. 14381 - 14384
(2015/01/09)
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- Straightforward syntheses of hypervalent iodine(III) reagents mediated by selectfluor
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(Chemical Equation Presented) Use of Selectfluor allows hypervalent iodine(III) species such as aryl iodine(III) difluoride, diacetate, and di(trifluoroacetate) and Koser's salt to be easily prepared. Aryl iodine(III) difluoride and diacetate can be synthesized from the corresponding arene and elemental iodine in one-pot procedures.
- Ye, Chengfeng,Twamley, Brendan,Shreeve, Jean'ne M.
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p. 3961 - 3964
(2007/10/03)
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- Rearrangement of phenylethenes on reaction with iodine-xenon difluoride
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(matrix presented) Phenyl-substituted ethenes react with iodine and xenon difluoride to provide difluorinated products. Iodofluoro intermediates react with xenon difluoride to produce transient iodine difluoride species that lose IF and F- and produce carbocations.
- Patrick, Timothy B.,Qian, Suntian
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p. 3359 - 3360
(2007/10/03)
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- Hexafluoropropene oxide - a fluorinating reagent for the formation of element-fluorine bonds
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Hexafluoropropene oxide (HFPO) is shown to be a good reagent for the nucleophilic formation of the element-fluorine bond in organoelement compounds. Fluorides of Bi, Sb, Se, Te and I were prepared from appropriate oxygen compounds.
- Lermontov,Rakov,Zefirov,Stang
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p. 103 - 105
(2007/10/03)
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- gem-Difluorination of 1,3-dithiolanes with the hexafluoropropene-diethylamine reagent and N-iodosuccinimide or 1,3-dibromo-5,5-dimethylhydantoin
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gem-Difluoro compounds are readily prepared from 1,3-dithiolanes in good yield on treatment with hexafluoropropene-diethylamine/1,3-dibromo-5,5-dimethylhydantoin or /N-iodosuccinimide/water. - Keywords: gem-Difluorination; 1,3-Dithiolanes; NMR spectroscop
- Shimizu, Makoto,Maeda, Takashi,Fujisawa, Tamotsu
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- Conversion of the Carbonyl Group to CF2 Using IF
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A novel method for the transformation of CO -> CF2 is described.The easily made hydrazone derivatives of the carbonyl moiety are reacted under mild conditions with IF prepared directly from the corresponding elements.Various hydrazones have been examined and compared with each other.Unsubstituted ones are usually the most suitable although they are not always easy to purify and store.N-Methyl- and N,N-dimethylhydrazones also give quite satisfactory results.The more easily made dinitrophenyl hydrazones (DNPs), semicarbazones, and tosylhydrazones also react, but the yields of the desired CF2 compounds are usually lower.Oximes could also be successfully reacted.The two main byproducts of the reaction are the parent carbonyl compounds, which can be recycled, and the α-iododifluoro derivatives.The latter upon treatment with LiAlH4 or Bu3SnH were reduced to the desired product, thus increasing the overall yields.
- Rozen, Shlomo,Zamir, Dov
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p. 4695 - 4700
(2007/10/02)
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- ROLE OF THE POLYMER BACKBONE ON THE REACTIVITY OF POLYMER-SUPPORTED (DICHLOROIODO)BENZENE
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Chlorination of iodinated crosslinked polystyrene with Cl2 gave polyaryliododichloride containing 1.1 mmol of active chlorine per gram of resin, while fluorination of the same iodinated resin with XeF2 gave polyaryliododifluoride, co
- Sket, Boris,Zupan, Marko,Zupet, Pavle
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p. 1603 - 1606
(2007/10/02)
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