88858-93-9

Upstream product

• 1689-71-0 cis-1,2-diphenyloxirane 
• 1689-71-0 2,3-diphenyloxirane 
• 1439-07-2 trans-Stilbene oxide 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 53313-88-5 Trifluoro-acetic acid 2-fluoro-1,2-diphenyl-ethyl ester 

Downstream Products

• 52776-26-8 (1R*, 2R*)-1-fluoro-2-methoxy-1,2-diphenylethane 

Relevant academic research and scientific papers

Metal-Free and User-Friendly Regioselective Hydroxyfluorination of Olefins

A simple, user-friendly, metal-free protocol for the regioselective anti-Markovnikov hydrofluorination of olefins using readily available and inexpensive reagents has been developed. This new approach displays a broader scope than previously reported methodologies and has been applied to the late-stage fluorination of a complex molecule, giving rise to a fluorosteroid derivative. The stereochemistry of the process has also been studied in some detail.

Palladium-catalyzed intermolecular fluoroesterification of styrenes: Exploration and mechanistic insight

A novel palladium-catalyzed intermolecular oxidative fluoroesterification of vinylarenes has been developed using NFSI, one of the mildest electrophilic fluorinating reagents. The reaction presents an efficient synthetic pathway to afford a series of α-monofluoromethylbenzyl carboxylates in good to excellent yields. Rather than following an electrophilic fluorination pathway, the reaction is initiated through oxidation of Pd(0) to a Pd(ii) fluoride complex by NFSI, followed by fluoropalladation of a styrene to generate an α-monofluoromethylbenzyl-Pd intermediate. Generally, reductive elimination of benzyl-PdII complexes is favored with relatively strong oxy-nucleophiles to afford C-O bonds. This reaction, however, exhibited the opposite reactivity: strong acids with weak nucleophilicity, such as CF 3CO2H and CCl3CO2H, were prone to afford the fluoroesterification product, while weak acids with strong nucleophilicity, such as HOAc and BzOH, did not deliver the C-O bond product. Further mechanistic studies determined that Csp3-Pd(O2CR), a key intermediate, was generated through ionic ligand exchange between benzyl-Pd(NZ2) and CF3CO2H, and the final C-O bond was possibly formed through reductive elimination of a high-valent Csp 3-Pd(O2CR) complex via an SN2-type nucleophilic attack pathway.

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,

Asymmetric oxidative α-fluorination of 2-alkylphenylacetaldehydes with AgHF2 and ruthenium/PNNP catalysts

During attempts directed at epoxide ring opening with different HF sources, we discovered that the Lewis acidic [RuCl(PNNP)]+ (1) or [Ru(OEt2)2(PNNP)]2+ (2) catalysts promote the [1,2]-phenyl shift (Meinwald rea

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

(Salen)chromium Complex Mediated Asymmetric Ring Opening of meso- And Racemic Epoxides with Different Fluoride Sources

The asymmetric ring opening of five meso-and three racemic epoxides with different fluorinating reagents in the presence of stoichiometric or slightly sub-stoichiometric amounts of Jacobsen's enantiopure (salen)chromium chloride complex A gave the corresponding optically active vicinal fluorohydrins. Silver fluoride was used as one of the fluoride sources either in the presence of Bu4N+H2F3- in diethyl ether or in acetonitrile. The latter reactions starting from cyclohexene oxide (1) showed maximum 72% ee in the formed fluorohydrin 2 isolated in 90% yield. From other meso-epoxides such as cyclopentene oxide and cycloheptene oxide the corresponding fluorohydrins were isolated in 80% and 82% yield with 65% and 62% ee, respectively. In case of ring opening under similar conditions of the racemic styrene oxide or phenyl glycidyl ether 83% and 75% of the fluorohydrins with fluorine in the primary position were isolated with 74% ee and 65% ee, respectively. Tetrahydronaphthalene oxide yielded a 2:1 mixture of trans- (23% ee) and cis-2-fluoro-3,4-benzocyclohexenol (2% ee) suggesting competing SN2 and SN1 type ring openings. Other epoxides such as cyclooctene oxide, cis-stilbene oxide and α-methylstyrene oxide did not react or gave the fluorohydrins with very small enantiomeric excess.

Potassium dihydrogen trifluoride: a novel fluorinating reagent for ring-opening of epoxides

It has been found that potassium dihydrogen trifluoride is an efficient and easy-to-handle solid reagent for the ring-opening reaction of epoxides giving fluorhydrins regio- and stereo-selectively.The reaction proceeds via cis-addition of HF to the epoxide. - Keywords: Potassium dihydrogen trifluoride; Fluorinating reagent; Ring-opening; Epoxides; Fluorohydrin synthesis

Site-Selective Fluorination of Organic Compounds Using 1-Alkyl-4-fluoro-1,4-diazabicyclooctane Salts (Selectfluor Reagents)

The new "N-F"-type electrophilic reagent family of 1-alkyl-4-fluoro-1,4-diazabicyclooctane salts (derived from elemental fluorine (F2) and 1-alkyl-1,4-diazabicyclooctane salts) has been found to be very effective for the fluorination of a wide variety of organic substrates.These include steroidal enol acetates and silyl enol ethers, phenyl-substituted olefins, sulfides bearing α-H atoms, certain carbanions, and mildly activated aromatic compounds.The products were obtained with good yields and regioselectivity under very mild reaction conditions.

SUBSTITUTION AND ADDITION REACTIONS OF ORGANIC SUBSTRATES WITH HYPOFLUOROUS ACID

The chemical reactions of hypofluorous acid with aromatic and olefinic substrates show considerable variety.Hypofluorous acid reacts with naphthalene to give 1-naphthol, 2-naphthol and 1,4-naphthoquinone: with benzothiophen to give the 1,1-dioxide; with trans-stilbene to give threo-2-fluoro-1-hydroxy-1,2-diphenylethane, benzophenone and diphenylacetaldehyde: and with cholesteryl acetate to give the two epoxides ( α:β=6.3:1 ) and two fluorohydrins ( 6β-fluoro-5-β-ol and 5α-fluoro-6β-ol ).