82907-01-5

Upstream product

• 637-87-6 1-Chloro-4-iodobenzene 
• 105417-08-1 trifluoroethenylzinc bromide 
• 116-14-3 polytetrafluoroethylene 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 79-38-9 Chlorotrifluoroethylene 
• 811-97-2 1,1,1,2-tetrafluoroethane 
• 72487-06-0 1-(4-chlorophenyl)-2,2,2-trifluoroethanol 
• 51833-36-4 4-chlorophenylmagnesium chloride 
• 1679-18-1 4-Chlorophenylboronic acid 
• 35692-30-9 (4-chlorophenyl)trimethoxysilane 
• 827605-29-8 2-(4-chloro-phenyl)-5,5-dimethyl-[1,3,2]dioxaborinane 

Relevant academic research and scientific papers

The method of manufacturing the same and hydroxybenzenes (trifluorolactic vinyl)

PROBLEM TO BE SOLVED: To provide (trifluorovinyl)benzenes and a method for producing the same.SOLUTION: The method for producing (trifluorovinyl)benzenes expressed by general formula (3) comprises carrying out a reaction of a phenyl boron compound with trifluorohaloethylenes in the coexistence of 1 to 100 equivalents of water with respect to the phenyl boron compound (1), a palladium complex coordinated with a bidentate phosphine ligand, and an alkali metal salt. In formula (3), Rrepresents a hydrogen atom or a formyl group; Rand Reach independently represents a hydrogen atom, 1-4C alkyl group, 2-4C alkenyl group, 2-5C acyl group, (1-4C alkoxy)carbonyl group, 1-4C alkoxy group, tri(1-4C alkyl)silyl group, 2-5C acylamino group, cyano group, phenyl group, chlorine atom, fluorine atom or nitro group; and adjoining Rand Rmay form a ring together with a carbon atom bonded thereto.

Base-free Hiyama coupling reaction via a group 10 metal fluoride intermediate generated by C-F bond activation

A Pd(0)-catalyzed Hiyama coupling reaction of tetrafluoroethylene (TFE) proceeded without the use of a base to give α,β,β- trifluorostyrene derivatives. A Ni(0)-catalyzed Hiyama coupling reaction of perfluoroarenes also occurred without a base. The key intermediate in these reactions would be a transition-metal fluoride complex that is generated in situ by the oxidative addition of a C-F bond.

Palladium-catalyzed base-free Suzuki-Miyaura coupling reactions of fluorinated alkenes and arenes via a palladium fluoride key intermediate

A new strategy for C-C bond formation with organoboronates through C-F activation of fluorinated alkenes and arenes was developed. In this Pd-catalyzed Suzuki-Miyaura-type cross-coupling reaction, neither a base for enhancing the reactivity of the organoboron reagents nor a Lewis acid for promoting C-F bond activation was required. A fluoropalladium intermediate played an essential role in this reaction. In addition, a Ni(NHC) catalyst was efficient for C-C coupling through C-F bond activation of fluoroarenes. Pd0/PR 3 complexes promote C-C bond formation with organoboronates through C-F bond activation of fluorinated alkenes. Mechanistic studies show that a PdII fluoride intermediate plays an essential role in this base-free cross-coupling reaction. Moreover, a Ni(NHC) catalyst is efficient for C-C coupling through C-F bond cleavage of fluoroarenes. Copyright

Preparation of trifluorostyrenes via palladium-catalyzed coupling of arylboronic acids with chloro- and bromotrifluoroethylene

A highly efficient and cost-effective method for the preparation of α,β,β-trifluorostyrene (TFS) and its derivatives is described. The method required only 0.2 mol % of Pd(dba)2 and 0.4 mol % of PtBu3 and occurred to full conversion within 2.0 h. With this method, a wide range of arylboronic acids were efficiently incorporated to generate α,β,β-trifluorostyrene derivatives.

Pd-catalyzed arylation of chlorotrifluoroethylene using arylboronic acids

The palladium-catalyzed cross-coupling of chlorotrifluoroethylene and arylboronic acids proceeds in the presence of a base and H2O to provide α,β,β-trifluorostyrene derivatives in satisfactory yields.

METHOD FOR PRODUCING SUBSTITUTED FLUORINE-CONTAINING OLEFIN

This invention relates to a method of reacting fluoroolefin with an organic magnesium compound in the presence of a catalyst comprising nickel or palladium so as to efficiently produce fluoroolefin, such as TFE, in which a fluorine (F) atom or atoms bonded to the sp2 hybridized carbon atom are substituted with an organic group.

Palladium-catalyzed coupling reactions of tetrafluoroethylene with arylzinc compounds

Organofluorine compounds are widely used in all aspects of the chemical industry. Although tetrafluoroethylene (TFE) is an example of an economical bulk organofluorine feedstock, the use of TFE is mostly limited to the production of poly(tetrafluoroethylene) and copolymers with other alkenes. Furthermore, no catalytic transformation of TFE that involves carbon-fluorine bond activation has been reported to date. We herein report the first example of a palladium-catalyzed coupling reaction of TFE with arylzinc reagents in the presence of lithium iodide, giving α,β,β-trifluorostyrene derivatives in excellent yields.

An efficient dehyrohalogenation method for the synthesis of α,β,β-trifluorostyrenes, α-chloro-β,β- difluorostyrenes and E-1-arylperfluoroalkenes

Dehydrofluorination of 1-aryl-1,2,2,2-tetrafluoroethanes (ArCHFCF 3) and 1-aryl-1-chloro-2,2,2-trifluoroethane (ArCHClCF3) using lithiumhexamethyldisilazide (LHMDS) in tetrahydrofuran (THF) at room temperature produced 1,2,2-trifluorostyrene and 1-chloro-2,2-difluorostyrene, respectively, in very good isolated yields. Dehydrofluorination of 1,2,2,3,3,3-hexafluoro-1-phenyl-propane (PhCHFCF2CF3) and 1,2,2,3,3,4,4,4-octafluoro-1-phenyl-butane (PhCHFCF2CF 2CF3) using LHMDS produced the corresponding substituted olefins (1-phenyl-1,2,3,3,3-pentafluoroprop-1-ene and 1-phenyl-1,2,3,3,4,4,4- pentafluorobut-1-ene) in good yield and high E-selectivity. Dehydrofluorination of 1-chloro-1-phenyl-2,2,3,3,3-pentafluoropropane (PhCHClCF2CF 3) and 1-chloro-1-phenyl-2,2,3,3,4,4,4-heptafluorobutane (PhCHClCF2CF2CF3) produced a mixture of the corresponding E and Z olefins (PhCClCFCF3 and PhCClCFCF 2CF3) in good yield.

Room temperature preparation of trifluoroethenylzinc reagent by metalation of the readily available halocarbon HFC-134a and an efficient, economically viable synthesis of 1,2,2-trifluorostyrenes

Trifluoroethenylzinc reagent [CF2=CFZnX] was generated from the readily available halocarbon HFC-134a by an in situ metalation-transmetalation procedure at temperatures near to room temperature (15-20 °C). By systematic standardization of the m

A highly efficient room temperature non-organometallic route for the synthesis of α,β,β-trifluorostyrenes by dehydrohalogenation

Various 1-aryl-1,2,2,2-tetrafluoroethanes (ArCHFCF3, Ar=phenyl, substituted phenyl, naphthyl, heteroaryl) were synthesized by the fluorination of the corresponding alcohols with DAST. Dehydrofluorination of ArCHFCF3 using lithium hexamethyldisilazide (LHMDS) base in THF at room temperature produced 1,2,2-trifluorostyrenes (ArCF=CF2) in 61-91% isolated yields. This procedure provides an excellent non-organometallic alternative to the generally used metallation-Pd(0) coupling methods.