337-72-4

Upstream product

• 60-29-7 diethyl ether 
• 453-18-9 methyl fluoroacetate 
• 459-72-3 ethyl 2-fluoroacetate 
• 450-95-3 2-fluoroacetophenone 
• 530-48-3 1,1-Diphenylethylene 
• 599-67-7 1,1-diphenylethanol 
• 73037-93-1 2-Fluoro-1-(trifluoromethoxy)-1,1-diphenylethane 
• 118268-22-7 C₂₁H₂₀FNO₂S 
• 379-83-9 1,2-Difluoro-1,1-diphenylethane 
• 119-61-9 benzophenone 
• 67-56-1 methanol 
• 98-80-6 phenylboronic acid 
• 70-11-1 α-bromoacetophenone 
• 65325-68-0 1-(monofluoromethyl sulfinyl)benzene 

Downstream Products

• 130728-72-2 4-phenyl-1,2-naphthalenedicarboxylic anhydride 
• 390-75-0 2-fluoro-1,1-diphenylethene 
• 466-35-3 2-fluoro-1-fluoromethyl-1,3,3-triphenyl-indan 
• 379-83-9 1,2-Difluoro-1,1-diphenylethane 
• 36586-15-9 (2-ethoxyethene-1,1-diyl)dibenzene 

Relevant academic research and scientific papers

Exploiting a beast in carbenoid chemistry: Development of a straightforward direct nucleophilic fluoromethylation strategy

The first direct and straightforward nucleophilic fluoromethylation of organic compounds is reported. The tactic employs a fleeting lithium fluorocarbenoid (LiCH2F) generated from commercially available fluoroiodomethane. Precise reaction conditions were developed for the generation and synthetic exploitation of such a labile species. The versatility of the strategy is showcased in ca. 50 examples involving a plethora of electrophiles. Highly valuable chemicals such as fluoroalcohols, fluoroamines, and fluoromethylated oxygenated heterocycles could be prepared in very good yields through a single synthetic operation. The scalability of the reaction and its application to complex molecular architectures (e.g., steroids) are documented.

Rh-Catalyzed arylation of fluorinated ketones with arylboronic acids

The Rh-catalyzed arylation of fluorinated ketones with boronic acids is reported. This efficient process allows access to fluorinated alcohols in high yields under mild conditions. Competition experiments suggest that difluoromethyl ketones are more reactive than trifluoromethyl ketones in this process, despite their decreased electronic activation, an effect we postulate to be steric in origin.

Microwave assisted fluorofunctionalization of phenyl substituted alkenes using selectfluor

A rapid fluorofunctionalization of alkenes and diene using selectfluor has been uncovered. The olefins such as 1-phenyl ethene; 1,1-diphenylethene; (E)-1,2-diphenylethene; (E)-1,2-dinaphthylethene; 1,1,2-triphenylethene; 1,1,2,2-tetraphenylethene and 1,1,

Transformations of organic molecules with F-TEDA-BF4 in ionic liquid media

The transformations of organic molecules with F-TEDA-BF4 (1) were investigated in the hydrophilic ionic liquid (IL) 1-butyl-3-methyl- imidazolium tetrafluoroborate ([bmim][BF4], 2) and the hydrophobic IL 1-butyl-3-methyl-imidazolium hexafluorophosphate ([bmim][PF6], 3). The range of substrates included alkyl substituted phenols 4a-c, 9, 13, 1,1-diphenylethene (15), alkyl aryl ketones 19-22, aldehydes 23-25 and methoxy-substituted benzene derivatives 26-30. The evaluation of the outcome of reactions performed in IL media in comparison to those of the corresponding reactions in conventional organic solvents revealed that the transformations in IL are less efficient and selective. The effect of the presence of a nucleophile (MeOH, H2O, MeCN) on the course of reaction was also studied.

Selective and effective fluorination of organic compounds in water using selectfluor F-TEDA-BF4

(Chemical Equation Presented) Selective and effective fluorination of various types of organic compounds performed in water as the reaction medium using 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor F-TEDA-BF

Effect of reaction conditions on the kinetic and activation parameters for the mild introduction of fluorine into phenyl-substituted alkenes with Accufluor(TM) NFTh

Evidence for a bimolecular process in mild fluorine transfer from the F- L type of reagent (electrophilic fluorinating reagent) is presented. The corresponding second-order rate constants for the fluorination of phenyl- substituted alkenes with 1-fluoro-4

Effect of reaction conditions on the kinetic and activation parameters for the mild introduction of fluorine into α-substituted styrenes with AccufluorTM NFTh

Kinetic studies on fluorination of α-substituted styrenes with 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (AccufluorTM NFTh) in acetonitrile or in acetonitrile in the presence of methanol or water as nucleophiles were carried out. These reactions exhibited overall second-order kinetics and formed Markovnikov type products. The corresponding second-order rate constants for fluorination of the studied substrates in the presence of methanol at 38.8 deg C are k2 = 1.1 x 10-3 M-1 s-1 for styrene (1a), 3.3 x 10-2 M-1 s-1 for α-methylstyrene (1b) and 3.4 x 10-2 M-1 s-1 for 1,1-diphenylethene (1c). The substitution of methanol as nucleophile by water had very little effect on the rate of the process. Solvent polarity variation (Grunwald-Winstein Ybenzyl) showed a similar small effect, too, indicating negligible change in the polarity of the rate-determining transition state in comparison with the reactants. Activation enthalpies (between 62 and 80 kJ mol-1) and activation antropies (between -74 and 32 J mol-1 K-1) were determined for fluorination of α-substituted styrenes with NFTh in acetonitrile in the presence of methanol and water as nucleophiles. Hammett correlation analysis of the reaction of substituted styrenes with NFTh in MeCN MeCN-H2O and MeCN-MeOH gave reaction constants ρ+ of -1.48, -1.52 and -1.80, respectively, which support our belief in the mainly non-polar character of the rate-determining transition state of the studied reactions.

1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) as a new, effective reagent for selective fluorofunctionalisation of alkenes under mild reaction conditions

1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) Accufluor NFTh) is confirmed as a highly effective reagent for introducing a fluorine atom into organic molecules across a phenyl-substituted carbon-carbon double bond. Quantitativ

A New, Selective Method for Conversion of Alcohols to Vicinal Fluorohydrins

Aryl-alkyl substituted tertiary alcohols are efficiently converted directly to vicinal fluorohydrins in high yield by reaction with 1-chloromethyl-4-fluoro-1,4-diazobicyclooctane bis(tetrafluoroborate) (SelectfluorTM F-Teda BF4) in aceto

N-Fluorobisimides: Reactions with Some Olefins via α-Fluoro Carbocationic Intermediates

N-Fluorobisimides are a new class of electrophilic fluorinating agents.Reaction of (CF3SO2)2NF (1) with olefins gave various products, depending on the reaction conditions and the structure of the substrate.In solvents of higher nucleophilicity such as H2O, acetic acid, aqueous HCl, and (HF)nPy, α-fluorohydrins and their acetates, α,β-chlorofluoro- and α,β-difluoroalkanes were obtained.In acetic acid, trans-stilbene and tetraphenylethylene produced the rearranged, nonfluorinated aldehyde and ketone.Evidence is presented for the reactions proceeding via a one-electron transfer mechanism involving α-fluorocarbocationic intermediates.