10541-59-0

Upstream product

• 100-42-5 styrene 
• 96-09-3 styrene oxide 
• 29443-54-7 1,1-diiodo-2-phenylethane 
• 345-62-0 (1-chloro-2,2-difluoro-ethyl)-benzene 
• 616-75-1 2-benzylmalonic acid 
• 100-39-0 benzyl bromide 
• 82255-42-3 2,2-difluoro-1-phenyl-ethanol 
• 122-78-1 phenylacetaldehyde 
• 62673-31-8 benzyl(bromo)zinc 
• 1422039-14-2 C₈H₇BrF₂Zn 
• 66310-10-9 N-benzyl-2,4,6-triphenylpyridinium tetrafluoroborate 
• 100-46-9 benzylamine 
• 28925-45-3 S-methyl O-benzyl dithiocarbonate 
• 100-51-6 benzyl alcohol 

Downstream Products

• 351-78-0 β-fluorostyrene 
• 345-62-0 (1-chloro-2,2-difluoro-ethyl)-benzene 

Relevant academic research and scientific papers

Preparation of 1,1-difluoroalkanes from aldehydes via 1,1-bistriflates: Advantageous use of HF-Lewis base reagents

Alkane-1,1-bistriflates, prepared in excellent yields by reaction of aldehydes with triflic anhydride, are converted to their respective 1,1-difluoroalkanes in good to excellent yield through reaction with fluorinating agent, triethylaminetrishydrofluorid

Hexafluoropropene oxide - a fluorinating reagent for the formation of element-fluorine bonds

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.

Copper-Catalyzed Deaminative Difluoromethylation

The difluoromethyl group (CF2H) is considered to be a lipophilic and metabolically stable bioisostere of an amino (NH2) group. Therefore, methods that can rapidly convert an NH2 group into a CF2H group would be of great value to medicinal chemistry. We report herein an efficient Cu-catalyzed approach for the conversion of alkyl pyridinium salts, which can be readily synthesized from the corresponding alkyl amines, to their alkyl difluoromethane analogues. This method tolerates a broad range of functional groups and can be applied to the late-stage modification of complex amino-containing pharmaceuticals.

Hypervalent Iodine-Mediated Fluorination of Styrene Derivatives: Stoichiometric and Catalytic Transformation to 2,2-Difluoroethylarenes

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.

Synthesis of 1,1-difluoroalkanes via phase transfer catalysed reaction of 1,1-bis-Triflates with KF in the presence of cocatalyst - Ph3SnF

1,1-bis-Triflates treated with KF in the presence of triphenyltin fluoride and tetrabutylammonium hydrogen sulfate give 1,1-difluoroalkanes.

Mild silver-mediated geminal difluorination of styrenes using an air- and moisture-stable fluoroiodane reagent

An air- and moisture-stable fluoroiodane in the presence of AgBF4 is suitable for selective geminal difluorination of styrenes under mild reaction conditions. One of the C-F bonds is formed by transfer of electrophilic fluorine from the hypervalent iodine reagent, while the other one arises from the tetrafluoroborate counterion of silver. Deuterium-isotope-labelling experiments and rearrangement of methyl styrene substrates suggest that the reaction proceeds through a phenonium ion intermediate. Phenomenal phenonium: A formal F2 addition to styrenes was carried out by using stable and safe fluorinating reagents under mild reaction conditions. The reaction proceeds via a phenonium intermediate.

Fluorodecarboxylation with Xenon Difluoride

The reaction between xenon difluoride and aliphatic carboxylic acids causes decarboxylation with replacement of the carboxyl group by fluorine.

Aryl Radical Activation of C-O Bonds: Copper-Catalyzed Deoxygenative Difluoromethylation of Alcohols

Given their ubiquity in natural products and pharmaceuticals, alcohols represent one of the most attractive starting materials for the construction of C-C bonds. We report herein the first catalytic strategy to harness the reactivity of aryl radicals for the activation of C-O bonds in alcohol-derived xanthate esters, allowing for the discovery of the first catalytic deoxygenative difluoromethylation reaction. Under copper-catalyzed conditions, a wide variety of alkyl xanthate esters, readily synthesized from alcohol feedstocks, were activated by catalytically generated aryl radicals and were converted to the alkyl-difluoromethane products via alkyl radical intermediates. This scalable protocol exhibits a broad substrate scope and functional group tolerance, enabling late-stage modification of complex pharmaceutical agents. A one-pot protocol has been developed that allows for the direct use of free alcohols without purification of the xanthate esters. Mechanistic studies are consistent with the hypothesis of aryl radicals being formed and initiating the cleavage of the C-O bonds of xanthate esters, to generate alkyl radicals as the key intermediates. This aryl radical activation approach represents a new strategy for the activation of alcohols as cross-coupling partners.

Synthetic method of difluoromethyl compound

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.

Reactions of organozinc reagents with potassium bromodifluoroacetate

A practical method for the synthesis of gem-difluorinated compounds from organozinc reagents is described. Potassium bromodifluoroacetate serves as a source of CF2-fragment, which is inserted into carbonzinc bond of organozinc reagents. The intermediate difluorinated organozinc species can be protonated, brominated or coupled with allylic electrophiles.