- Solid-phase synthesis on functionalised fluoropolymer resins. Part 2: Preparation and properties of functional merrifieldtype resins possessing a perfluorinated polymer backbone
-
Monomers α,β,β-trifluorostyrene and 4-methyl-α,β,β- trifluorostyrene were prepared and were copolymerised under free-radical emulsion conditions to give highly stable, well defined lipophilic polymer resins. Benzylic halogenation of the polymer products gave 4-chloromethyl and 4-bromomethyl derivatives which could be elaborated through nucleophilic displacement of halide. The reaction of 4-fluorophenol with the 4- chloromethylated poly(trifluorostyrene) resin was followed by 1H and 19F NMR spectroscopy and proceeded more rapidly than for Merrifield resin. (C) 2000 Elsevier Science Ltd.
- Liu, Shuyuan,Akhtar, Mahmoud,Gani, David
-
-
Read Online
- Synthesis method of aryl trifluoroethylene compound
-
The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthesis method of an aryl trifluoroethylene compound, and the main improvement lies in that trifluoroethylene and aryl sulfinate are used as raw materials and react under the catalytic action of a transition metal salt to obtain the aryl trifluoroethylene compound. The selected arylation reagent is novel, the reaction condition is simple and mild, the cost is low, the operation is easy and convenient, the cost is low, the universality is wide, the environmental pollution is small and the atom economy is high, and industrial large-scale production is expected to be achieved.
- -
-
Paragraph 0037-0041; 0046-0081
(2021/04/10)
-
- Post-treatment method of trifluorostyrene synthesis liquid
-
The invention discloses a post-treatment method of a trifluorostyrene synthesis liquid. The method comprises: distilling a synthesis liquid, and rectifying the distillate to prepare trifluorostyrene.According to the invention, the method has the advantages of short post-treatment route, high yield and easiness in industrialization, and more importantly the solvent THF is easy to recover, so thatthe manufacturing cost of trifluorostyrene is favorably reduced, and industrial production is convenient to realize.
- -
-
Paragraph 0020; 0034; 0056-0103
(2020/04/22)
-
- Solvent- A nd anion-dependent rearrangement of fluorinated carbene ligands provides access to fluorinated alkenes
-
The construction of fluorocarbene ligands within the coordination sphere of transition metal complexes using sequential nucleophilic and electrophilic addition to a vinylidene complex is described. Reaction of [Ru(η5-C5H5)(dppe)(CCPhF)][N(SO2Ph)2] with [NMe4]F results in nucleophilic attack of fluoride at the metal-bound carbon of the vinylidene ligand to give alkenyl complex [Ru(η5-C5H5)(dppe)(-CFCFPh)]. Subsequent eletrophilic fluorination with N-fluorobenzenesulfonimide (NFSI) results in the formation of the fluorinated carbene complex [Ru(η5-C5H5)(dppe)(CF-CHFPh)][N(SO2Ph)2]. The fluorocarbene complexes undergo rearrangement to liberate free fluorinated alkenes, a process governed by the choice of solvent and anion, representing a new metal-mediated route to fluorinated alkenes from alkynes.
- Hall, Lewis M.,Milner, Lucy M.,Hart, Sam J.,Whitwood, Adrian C.,Lynam, Jason M.,Slattery, John M.
-
supporting information
p. 17655 - 17659
(2019/12/23)
-
- The organic group is substituted with a fluorine-containing olefin production
-
PROBLEM TO BE SOLVED: To provide a production method that can produce a fluorine-containing olefin substituted with an organic group from a fluorine-containing olefin conveniently and efficiently (high yield, high selectivity, low cost).SOLUTION: The method for producing a fluorine-containing olefin substituted with an organic group includes a step of reacting a fluorine-containing olefin with an organosilicon compound in the presence of an organic transition metal catalyst containing a transition metal selected from among nickel, palladium, platinum, rhodium, ruthenium and cobalt.
- -
-
Paragraph 0093
(2019/01/06)
-
- Method for synthesizing trifluoroarylethene compounds
-
The invention relates to a method for synthesizing trifluoroarylethene compounds, belonging to the field of chemical synthesis. According to the method, trifluoroethylene is used as a starting raw material and reacts with easily available iodonium salts under proper conditions to produce the trifluoroarylethene compounds. Compared with traditional methods, the synthetic method provided by the invention has the characteristics of good universality, short reaction time, easy operation and the like; and since the synthetic method has the advantages of low cost, simple process, low pollution and the like, large-scale industrial production of the synthetic method can be realized.
- -
-
Paragraph 0030-0075
(2018/05/16)
-
- Fluorinated Vinylsilanes from the Copper-Catalyzed Defluorosilylation of Fluoroalkene Feedstocks
-
Herein, a copper-catalyzed C?F bond defluorosilylation reaction of tetrafluoroethylene and other polyfluoroalkenes is described. Mechanistic studies, based on a series of stoichiometric reactions with copper complexes, revealed that the key steps of this defluorosilylation reaction are 1) the 1,2-addition of a silylcopper intermediate to the polyfluoroalkene and 2) a subsequent selective β-fluorine elimination, which generates a Cu?F species. The β-fluorine elimination is facilitated by Lewis acidic F?Bpin, which is generated in situ during the defluorosilylation.
- Sakaguchi, Hironobu,Ohashi, Masato,Ogoshi, Sensuke
-
supporting information
p. 328 - 332
(2017/12/13)
-
- A synthetic refrigeration working group ethylene group compound (by machine translation)
-
The invention relates to a synthetic refrigeration working group ethylene group compounds, is 1, 1 - dibromo - 1, 2, 2, 2 - tetrafluoroethane as raw materials, in under the action of the metal or metal compound, to obtain corresponding trifluorovinyl metal complex. This trifluoro vinyl metal complex in the catalyst and the like with the active substances under the action of the coupling reaction, containing the trifluoro ethylene group compound. The method of the invention easy availability of raw materials, the method is simple, the production safety, is a suitable for industrial production method. (by machine translation)
- -
-
Paragraph 0023; 0024
(2017/07/21)
-
- FLUORINE-CONTAINING COMPLEX COMPOUND AND METHOD FOR PRODUCING FLUORINE-CONTAINING ORGANIC COMPOUND USING FLUORINE-CONTAINING COMPLEX COMPOUND
-
PROBLEM TO BE SOLVED: To provide a fluorine-containing complex compound capable of synthesizing a fluorine-containing compound having organic groups at both terminals of a tetrafluoroethylene structure; and a method for producing and using the same. SOLUTION: There are provided: a method for producing [1] a fluorine-containing organic metal compound represented by the formula (1a): R1-CF2-CF2-M1 (1a) [M1 represents a metal selected from copper, zinc, nickel, iron, cobalt or tin and R1 represents an organic group] and [2] a fluorine-containing complex compound containing a ligand selected from a pyridine ring-containing compound or a phosphine, which comprises a step of reacting an organosilicon compound which is silicic acid having a moiety represented by the partial structural formula (2a): R1-Si, an ester thereof or a salt thereof with a hydroxide, a halide, an alkoxide, an aryloxide compound of a metal M1, a ligand and tetrafluoroethylene; and a fluorine-containing complex compound using the same. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
- -
-
Paragraph 0096
(2018/09/25)
-
- Trifluoromethylphenylcarbenes. Carbene-Carbene Interconversion on the Singlet Energy Surface and Rearrangement to Trifluorobenzocyclobutene, Trifluorostyrene, and Trifluoromethylfulvenallenes
-
The four isomeric α-, ortho-, meta-, and para-trifluoromethylphenylcarbenes were generated by photolysis of the corresponding 3-phenyl-3-trifluoromethyldiazirene 1 or the four isomeric trifluoromethylphenyldiazomethanes 2 and 4-6. The four corresponding triplet trifluoromethylphenylcarbenes 3 and 7-9 were observed by electron spin resonance (ESR) spectroscopy in Ar matrices at 14K. The α- and ortho-carbenes 3 and 7 and the ortho- and para-carbenes 7 and 9 interconvert partially when generated by short-wavelength photolysis (350nm) before intersystem crossing to the triplet states. The triplet states do not undergo further Carbene-Carbene interconversion. The interconversions are assumed to take place via the meta-trifluoromethylphenylcarbene 8. When the ortho- and para-carbenes are generated by long-wavelength photolysis (>450nm), the discrete, non-interconverting triplet carbenes are observed in the ESR spectra. Flash vacuum thermolysis of the diazirene 1 at 500°C afforded a mixture of bis(trifluoromethyl)heptafulvalenes 11, bis(trifluoromethyl)stilbenes 12, and bis(trifluoromethyl)anthracenes 13, and the presence of their likely precursor(s), trifluoromethylcycloheptatetraene(s), was confirmed by a peak at 1830cm-1 in the Ar matrix IR spectrum. In addition, at 700°C, four monomeric carbene rearrangement products were isolated and characterised, viz. 1,1,2-trifluorobenzocyclobutene 14, 1′,2′,2′-trifluorostyrene 15, and 1- and 2-trifluoromethylfulvenallenes 16 and 17.
- Blanch, Rodney J.,Wentrup, Curt
-
-
- Copper(0)-mediated fluoroalkylation of iodobenzene with 2-bromo-1,1,2,2-tetrafluoroethyl compounds: Investigation on the influence of R substituent on the reactivity of RCF2Cu species
-
We have made a systematic investigation on the copper(0)-mediated tetrafluoroethylenation of iodobenzene with structurally diverse 2-bromo-1,1,2,2-tetrafluoroethyl compounds. A comparison of this reaction with 1,2,2-trifluoro-1-phenylethylation and the known functionalized difluoroalkylation demonstrates that the substituent R of α,α-difluoroalkyl copper species RCF2Cu plays a crucial role on their reactivity, which is believed to be useful for the development of new fluoroalkylation reactions under the promotion of transition metals.
- Zhu, Jieming,Ni, Chuanfa,Gao, Bing,Hu, Jinbo
-
p. 139 - 147
(2015/03/04)
-
- Copper-mediated one-pot synthesis of trifluorostyrene derivatives from tetrafluoroethylene and arylboronate
-
We developed the copper-mediated synthesis of trifluorostyrene derivatives. β-Fluorine elimination of a 2-aryl-1,1,2,2- tetrafluoroethylcopper complex, generated in situ from arylboronate, copper tert-butoxide, and 1,10-phenanthroline with tetrafluoroethylene (TFE) via carbocupration, was promoted by the addition of a Lewis acid. The present reaction system was applied to the one-pot synthesis of various trifluorostyrene derivatives, through the transmetalationcarbocuprationβ-fluorine elimination sequence.
- Kikushima, Kotaro,Sakaguchi, Hironobu,Saijo, Hiroki,Ohashi, Masato,Ogoshi, Sensuke
-
supporting information
p. 1019 - 1021
(2015/08/24)
-
- Α, β, β-trifluorolactic of industrial manufacturing method (by machine translation)
-
PROBLEM TO BE SOLVED: To provide a method of producing industrially α,β,β-trifluorostyrenes. SOLUTION: The method of producing industrially the α,β,β-trifluorostyrenes includes a dehydrofluorination step of reacting α-aryl-α,β,β,β-tetrafluoroethanes with an alkali metal-bis(trimethylsilyl) amide, in the production of α,β,β-trifluorostyrenes, and an after-treatment step executed followed thereto to react a mixture containing the α,β,β-trifluorostyrenes of objective products and bis-(trimethylsilyl) amine of a byproduct with hydrogen fluoride, or a salt or a complex comprising an organic base and hydrogen fluoride. COPYRIGHT: (C)2012,JPO&INPIT
- -
-
Paragraph 0038-0043
(2018/12/12)
-
- Fluoroalkylcopper(I) complexes generated by the carbocupration of tetrafluoroethylene: Construction of a tetrafluoroethylene-bridging structure
-
We report a copper-mediated synthesis of a variety of 1,2-difunctionalized-1,1,2,2-tetrafluoroethylene derivatives via the carbocupration of tetrafluoroethylene. The key synthetic intermediates, 2-aryl-1,1,2,2-tetrafluoroethylcopper complexes, can be easily prepared, stored, and used as fluoroalkylation reagents. The molecular structure was unambiguously determined by X-ray crystallography and NMR analysis. We applied this method to the short-step synthesis of a liquid-crystalline compound bearing a tetrafluoroethylene-bridging structure.
- Saijo, Hiroki,Ohashi, Masato,Ogoshi, Sensuke
-
supporting information
p. 15158 - 15161
(2014/12/11)
-
- 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.
- Saijo, Hiroki,Sakaguchi, Hironobu,Ohashi, Masato,Ogoshi, Sensuke
-
supporting information
p. 3669 - 3672
(2014/08/18)
-
- PREPARATION METHOD FOR FLUORINE-CONTAINING OLEFINS HAVING ORGANIC-GROUP SUBSTITUENTS
-
An object of the present invention is to provide a method that enables the easy and efficient (high yield, high selectivity, low cost) preparation of a fluorine-containing olefin substituted with an organic group or groups from a fluorine-containing olefin. [Solution] The method for preparing a fluorine-containing olefin substituted with an organic group or groups, the method comprising a step of reacting a fluorine-containing olefin with an organic boron compound in the presence of an organic transition metal catalyst containing at least one transition metal selected from the group consisting of nickel, palladium, platinum, rhodium, ruthenium, and cobalt.
- -
-
Paragraph 0309
(2014/01/07)
-
- Preparation of trifluorovinyl compounds by lithium salt-promoted monoalkylation of tetrafluoroethene
-
Treatment of tetrafluoroethene (TFE) with diethylzinc in the presence of lithium iodide gave 1,1,2-trifluoro-1-butene in moderate yield. In the absence of lithium iodide, however, the nucleophilic addition of diethylzinc to TFE proceeded very slowly to afford ethyl 1,1,2,2-tetrafluorobutylzinc. The addition of lithium iodide to a solution of ethyl-1,1,2,2-tetrafluorobutylzinc resulted in a smooth transformation into 1,1,2-trifluoro-1-butene. In the presence of lithium chloride, the reaction of TFE with benzyl or allyl Grignard reagents afforded the corresponding monosubstituted products in good to excellent yields.
- Ohashi, Masato,Kamura, Ryohei,Doi, Ryohei,Ogoshi, Sensuke
-
supporting information
p. 933 - 935
(2013/09/02)
-
- 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
- Ohashi, Masato,Saijo, Hiroki,Shibata, Mitsutoshi,Ogoshi, Sensuke
-
p. 443 - 447
(2013/02/26)
-
- 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.
- -
-
Page/Page column 7
(2013/02/28)
-
- 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.
- Xu, Chunfa,Chen, Sheng,Lu, Long,Shen, Qilong
-
supporting information
p. 10314 - 10320
(2013/01/15)
-
- The stereoselective synthesis of (Z)-HFC=CFZnI and stereospecific preparation of (E)-1,2-difluorostyrenes from (Z)-HFC=CFZnI via an unusual Pd(PPh3)4-Cu(I)Br co-catalysis approach or (Z)-HFC=CFSnBu3
-
(Z)-HFCCFZnI was stereoselectively synthesized from activated zinc dust and (Z)-HFCCFI that was synthesized from chlorotrifluoroethene in a sequential manner. Compared to (E)-HFCCFZnI, (Z)-HFCCFZnI was more challenging to prepare in terms of sluggish metallation and formation of by-products, and underwent slower and incomplete Negishi coupling with aryl iodides. In a modification of Negishi coupling, (E)-α,β-difluorostyrenes were stereospecifically prepared in good to excellent yields under mild conditions from aryl iodides and (Z)-HFCCFZnI with the co-catalysis of Pd(PPh3)4/Cu(I)Br. Experimental investigation and mechanistic rationalization suggested that Cu(I)Br would be a scavenger of free ligands for the facilitation of Pd(PPh 3)2 formation, and a supplier of ligand for the metathesis process. Alternatively, (Z)-HFCCFSnBu3 and aryl iodides with an electron-withdrawing group underwent Stille-Liebiskind coupling to afford (E)-α,β-difluorostyrenes.
- Liu, Qibo,Burton, Donald J.
-
scheme or table
p. 78 - 87
(2011/03/22)
-
- 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.
- Ohashi, Masato,Kambara, Tadashi,Hatanaka, Tsubasa,Saijo, Hiroki,Doi, Ryohei,Ogoshi, Sensuke
-
supporting information; experimental part
p. 3256 - 3259
(2011/04/24)
-
- 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.
- Anilkumar,Burton, Donald J.
-
p. 1174 - 1184
(2007/10/03)
-
- 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
- Raghavanpillai, Anilkumar,Burton, Donald J.
-
p. 7083 - 7091
(2007/10/03)
-
- 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.
- Anilkumar,Burton, Donald J.
-
p. 6661 - 6664
(2007/10/03)
-
- A remarkable room temperature preparation of the trifluorovinylzinc reagent from HFC-134a. A cost-effective, high yield synthesis of α,β,β-trifluorostyrenes
-
The reaction of LDA (2.0 equiv.) with a THF solution of ZnCl2 (1.0 equiv.) and CF3CFH2 (HFC-134a) (1.2 equiv.) at 15-20°C gives a 73% yield of [F2C=CFZnCl]. Addition of R-C6H4I and Pd(PPhs
- Anilkumar,Burton, Donald J
-
p. 2731 - 2733
(2007/10/03)
-
- Synthesis and polymerization of p-pentamethyldisiloxanyl-α,β,β-trifluorostyrene and the oxygen permeability of the polymer
-
A novel monomer, p-pentamethyldisiloxanyl-α,β,β-trifluorostyrene, has been synthesized and polymerized to give a white polymer.Membranes obtained from the polymer exhibited an oxygen permeability coefficient (PO2: cc(STP) cm/cm2scmHg) and an oxygen separation factor (α=PO2/PO2) of 1.8 * 10-9 amd 2.4, respectively.The PO2 value is considerably higher than values for other poly(mono-substituted tetrafluoroethylenes).The introduction of a pentamethyldisiloxanylphenyl group into poly(tetrafluoroethylene) has been found to be very effective the enhancement of PO2 values.
- Aoki, Toshiki,Watanabe, Jun,Ishimoto, Yoshiyuki,Oikawa, Eizo,Hayakawa, Yoshio,Nishida, Masakazu
-
p. 285 - 288
(2007/10/02)
-
- Palladium - Catalyzed Cross - Coupling of Perfluoroalkenylzinc Reagents with Aryl Iodides. A New, Simple Synthesis of α,β,β-Trifluorostyrenes and the Stereoselective Preparation of 1-Arylperfluoroprepanes
-
Perfluoroalkenylzinc reagents coupled with aryl iodides in the presence of Pd(PPh3)4 (1-3 molpercent) to give the corresponding arylalkenes.A series of substituted α,β,β-trifluorostyrenes were prepared in good yields.This method provides ready availability of these fluorinated styrenes, which were previously obtained with difficulty.For the first time, 1-arylperfluoropropenes were prepared stereoselectively.Palladium-catalyzed reactions of 2 with aryl iodides gave stereospecific (E)-1-arylperfluoropropenes, and the same procedure with 3 gave stereoselective Z/E ratios ranging from 98/2 to 92/8.
- Heinze, Pamela L.,Burton, Donald J.
-
p. 2714 - 2720
(2007/10/02)
-
- PALLADIUM CATALYZED COUPLING OF F-VINYL ZINC REAGENTS WITH ARYL IODIDES. AN IMPROVED SYNTHESIS OF α,β,β-TRIFLUOROSTYRENES AND THE STEREOSPECIFIC PREPARATION OF 1-PHENYL-F-PROPENES
-
Palladium catalyzed coupling of trifluorovinyl zinc reagents with substituted aryl iodides provides a practical high yield route to α,β,β-trifluororstyrenes.Ortho, meta, and para substituted aryl iodides all work equally well.Similar coupling with E- and Z-1-iodo-F-propenes outlines the first stereospecific preparative route to 1-aryl-F-olefins.This approach provides a rapid, easily scaled-up synthesis via a one pot procedure to these valuable styrenes from commercially available precursors without recourse to low temperature processes or the use of unstable reaction intermediates.
- Heinze, Pamela L.,Burton, Donald J.
-
p. 115 - 120
(2007/10/02)
-