20372-72-9

Upstream product

• 666-23-9 phenyltetrafluorophosphorane 
• 36402-34-3 1-chloro-2-phenyl-2-(trimethylsiloxy)ethane 
• 100-42-5 styrene 
• 593-78-2 methyl hypochlorite 
• 7651-91-4 N,N-dichloromethylamine 
• 1674-30-2 1-phenyl-2-chloroethanol 
• 622-24-2 2-phenylethyl chloride 
• 2932-58-3 2-fluoro-2-phenylethanol 

Downstream Products

• 696-31-1 α-fluorostyrene 

Relevant academic research and scientific papers

Visible light-promoted metal-free C-H activation: Diarylketone-catalyzed selective benzylic mono- and difluorination

We report herein an operationally simple method for the direct conversion of benzylic C-H groups to C-F. We show that visible light can activate diarylketones to abstract a benzylic hydrogen atom selectively. Adding a fluorine radical donor yields the benzylic fluoride and regenerates the catalyst. The selective formation of mono- and difluorination products can be achieved by catalyst control. 9-Fluorenone catalyzes benzylic C-H monofluorination, while xanthone catalyzes benzylic C-H difluorination. The scope and efficiency of this new C-H fluorination method are significantly better than those of the existing methods. This is also the first report of selective C-H gem-difluorination.

Halofluorination of alkenes using trihaloisocyanuric acids and HF-pyridine

Halofluorination of alkenes with a new system (trihaloisocyanuric acids and HF-pyridine) results in the formation of vicinal halofluoroalkanes. The reaction is regioselective leading to Markovnikov-oriented products and the halofluorinated adducts follow anti-addition in the case of cyclohexene and 1-methylcyclohexene. Reaction yields range from 67-88%. Georg Thieme Verlag Stuttgart · New York.

Fluorination with ionic liquid EMIMF(HF)2.3 as mild HF source

Hydrogen fluoride is a basic fluorinating reagent, but handling it is difficult. For this reason, some modified fluorinating reagents such as HF-pyridine, Et3N-HF, and poly(hydrogen fluoride) complex have been developed. Those reagents, however, still require aqueous work-up procedures which generate hydrogen fluoride. Recently, ionic liquids have received much attention because of the ease in handling them and the possibility of non-aqueous work-up. An ionic liquid, 3-ethyl-1-methyimidazolium oligo hydrogen fluoride (EMIMF(HF)2.3), which is stable in air and moisture, can be used as a hydrogen fluoride equivalent for some fluorination reactions; it does not require an aqueous work-up.

Generation of interhalogen fluorides under mild conditions: A comparison of sluggish and reactive interhalogen fluorides

Interhalogen fluorides (XF; X = I, Br, or Cl) generated from xenon difluoride (XeF2) or triethylamine trihydrofluoride (TREAT HF) with iodine (I2), N-halosuccinimides (NXS; X = I, Br, or Cl), or alkylhypohalites (ROX; R = CH3 or t-Bu, X = Br or Cl) with alkenes and aromatics are reported. A comparison of the above reactions with other methods reported in the literature to generate interhalogen fluorides is made. Interhalogens generated from direct action of elemental fluorine (F2) or XF3 (X = I, Br, or Cl) with chlorine (Cl2), bromine (Br2), or iodine (I2) give a species that can react with electron-deficient alkenes or aromatics. These reagents are too reactive for electron-rich substrates. Interhalogen fluorides from reagents like NXS or ROX with XeF2 or amine HF are much less reactive and give good yields with electron-rich akenes or aromatics.

TETRABUTYLAMMONIUM DIHYDROGENTRIFLUORIDE: AN EFFECTIVE SOURCE OF FLUORIDE ION FOR HALOFLUORINATION OF ALKENES

Vicinal halofluorides have been prepared from the corresponding alkenes by reaction with a stoichiometric amount of Bu4N+H2F3- as a source of fluoride anion and an excess of an N-halosuccinimide (NXS).The reaction products are obtained in good yields, with a prevalent Markownikoff regiochemistry.Olefins containing hydroxy, epoxy, acetoxy and alkoxy groups do not undergo side reactions under these reaction conditions.

BORON TRIFLUORIDE PROMOTED REACTIONS OF N-HALOELECTROPHILES WITH ALKENES

N-Haloelectrophiles react with alkenes in the presence of boron trifluoride etherate to give halofluorides and N-halo adducts.

Conformational Studies on 2-Fluoro-1,2-disubstituted Ethanes by NMR Spectroscopy. Influence of Electronegativity on Vicinal Proton-Proton and Fluorine-Proton Coupling Constants

The analysis of the ABKX spectra of thirteen compounds of the series RC(H-K)(F-X)C(H-A)(H-B)X gave the four vicinal proton-proton and fluorine-proton coupling constants.These coupling constants of conformationally mobile structures were used (i) to calcul

Boron Trifluoride Promoted Reaction of Alkyl Hypohalites with Alkenes. A New Synthesis of Fluoro Halides

The reactions of the following alkenes with alkyl hypohalites and boron trifluoride (BF3) were investigated: cyclohexene (3), 1-hexene (8), trans-1,2-dichloroethylene (15), methyl acrylate (18), methyl crotonate (25), methyl isocrotonate (29), butadiene (33), methyl vinyl ketone (42), and styrene (45).Reactions of these alkenes with methyl hypochlorite (1) and BF3 in dichloromethane give fluoro chloride adducts as well as methoxy chlorides with the percentage of fluoro chlorides varying from 75percent for 29 to 8percent for 45.Fluoro bromide adducts are obtained with methyl hypobromite (2).Reactions with the tert-butyl hypohalites and BF3 also give fluoride incorporation.The percentage of fluoride incorporation with 1 or 2 is significantly greater in carbon tetrachloride than in dichloromethane.