- Synthesis and Characterization of Bidentate (P^N)Gold(III) Fluoride Complexes: Reactivity Platforms for Reductive Elimination Studies
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A new family of cationic, bidentate (P^N)gold(III) fluoride complexes has been prepared and a detailed characterization of the gold-fluoride bond has been carried out. Our results correlate with the observed reactivity of the fluoro ligand, which undergoes facile exchange with both cyano and acetylene nucleophiles. The resulting (P^N)arylgold(III)C(sp) complexes have enabled the first study of reductive elimination on (P^N)gold(III) systems, which demonstrated that C(sp2)?C(sp) bond formation occurs at higher rates than those reported for analogous phosphine-based monodentate systems.
- Genoux, Alexandre,Biedrzycki, Micha?,Merino, Estíbaliz,Rivera-Chao, Eva,Linden, Anthony,Nevado, Cristina
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supporting information
p. 4164 - 4168
(2020/12/23)
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- Preparation method of 2,6-difluorobenzamide
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The invention provides a preparation method of 2,6-difluorobenzamide with hydrogen fluoride as a reaction raw material, wherein the method improves the atom utilization rate of the reaction, can produce a byproduct acid, effectively reduces the production cost of the product, and improves the market competitiveness of the product; besides, the whole process does not generate mixed waste salt, and the process flow is simple.
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Paragraph 0074-0079; 0082-0085; 0086-0090; 0091-0094; 0095
(2021/05/29)
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- Method for dehydrating primary amide into nitriles under catalysis of cobalt
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The invention provides a method for dehydrating primary amide into nitrile. The method comprises the following steps: mixing primary amide (II), silane, sodium triethylborohydride, aminopyridine imine tridentate nitrogen ligand cobalt complex (I) and a reaction solvent under the protection of inert gas, carrying out reacting at 60-100 DEG C for 6-24 hours, and post-treating reaction liquid to obtain a nitrile compound (III). According to the invention, an effective method for preparing nitrile compounds by cobalt-catalyzed primary amide dehydration reaction by using the novel aminopyridine imine tridentate nitrogen ligand cobalt complex catalyst is provided; and compared with existing methods, the method has the advantages of simple operation, mild reaction conditions, wide application range of reaction substrates, high selectivity, stable catalyst, high efficiency, and relatively high practical application value in synthesis.
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Paragraph 0114-0116
(2021/06/21)
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- Synthesis method of insecticide teflubenzuron and intermediate 2,6-difluorobenzamide of insecticide teflubenzuron
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The invention discloses a synthesis method of an insecticide teflubenzuron and an intermediate 2,6-difluorobenzamide of the insecticide teflubenzuron, belonging to the field of pesticides. The synthesis method comprises the following steps: step 1, preparation of 2,6-dichlorobenzylidene chloride: preparing turbid liquid of dichlorotoluene and phosphorus pentachloride, introducing chlorine gas, layering materials by utilizing a gas-liquid separator, collecting a crude product, and rectifying the crude product to obtain the 2,6-dichlorobenzylidene chloride; and 2, preparation of 2,6-dichlorobenzonitrile: mixing 2,6-dichlorobenzylidene chloride, acetic acid, zinc chloride, hydroxylamine hydrochloride and sodium acetate, carrying out heating for a reflux reaction, conducting cooling, stirring,filtering and drying successively after the reaction is completed so as to obtain 2, 6-dichlorobenzonitrile. By adopting a one-pot method, a reaction route is shortened, total yield is increased to 67.3% from conventional 55.4%, and cost is greatly reduced.
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- Mechanistic Insights into C(sp2)?C(sp)N Reductive Elimination from Gold(III) Cyanide Complexes
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A new family of phosphine-ligated dicyanoarylgold(III) complexes has been prepared and their reactivity towards reductive elimination has been studied in detail. Both, a highly positive entropy of activation and a primary 12/13C KIE suggest a late concerted transition state while Hammett analysis and DFT calculations indicate that the process is asynchronous. As a result, a distinct mechanism involving an asynchronous concerted reductive elimination for the overall C(sp2)?C(sp)N bond forming reaction is characterized herein, for the first time, complementing previous studies reported for C(sp3)?C(sp3), C(sp2)?C(sp2), and C(sp3)?C(sp2) bond formation processes taking place on gold(III) species.
- Genoux, Alexandre,González, Jorge A.,Merino, Estíbaliz,Nevado, Cristina
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supporting information
p. 17881 - 17886
(2020/08/19)
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- Palladium-Catalyzed Cyanation under Mild Conditions: A Case Study to Discover Appropriate Substrates among Halides and Pseudohalides
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A case study has been effectively carried out to identify a suitable substrate among halides and pseudohalides for the palladium-catalyzed cyanation reactions under mild conditions. Among the various substrates considered for evaluation, aryl pentafluorobenzenesulfonates and nonaflates were identified to be the best substrates when compared to corresponding halides and pseudohalides. The substoichiometric use of nontoxic, environmentally benign potassium hexacyanoferrate as a cyanide source and exceptionally milder conditions further highlights the significance of the protocol developed. A wide range of electronically biased and sterically challenging substrates provided the corresponding the nitriles in good to excellent yields.
- Rajendra, Merla Arjuna,Sunil,Sajith, Ayyiliath Meleveetil,Joy, Muthipeedika Nibin,Bakulev, Vasiliy A.,Haridas, Karickal Raman
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supporting information
p. 1629 - 1633
(2020/09/15)
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- Efficient dehydration of primary amides to nitriles catalyzed by phosphorus-chalcogen chelated iron hydrides
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A series of phosphorus-chalcogen chelated hydrido iron (II) complexes 1–7, (o-(R'2P)-p-R-C6H4Y)FeH (PMe3)3 (1: R = H, R' = Ph, Y = O; 2: R = Me, R' = Ph, Y = O; 3: R = H, R' = iPr, Y = O; 4: R = Me, R' = iPr, Y = O; 5: R = H, R' = Ph, Y = S; 6: R = Me, R' = Ph, Y = S; 7: R = H, R' = Ph, Y = Se), were synthesized. The catalytic performances of 1–7 for dehydration of amides to nitriles were explored by comparing three factors: (1) different chalcogen coordination atoms Y; (2) R' group of the phosphine moiety; (3) R substituent group at the phenyl ring. It is confirmed that 5 with S as coordination atom has the best catalytic activity and 7 with Se as coordination atom has the poorest catalytic activity among complexes 1, 5 and 7. Electron-rich complex 4 is the best catalyst among the seven complexes and the dehydration reaction was completed by using 2 mol% catalyst loading at 60 °C with 24 hr in the presence of (EtO)3SiH in THF. Catalyst 4 has good tolerance to many functional groups. Among the seven iron complexes, new complexes 3 and 4 were obtained via the O-H bond activation of the preligands o-iPr2P(C6H4)OH and o-iPr2P-p-Me-(C6H4)OH by Fe(PMe3)4. Both 3 and 4 were characterized by spectroscopic methods and X-ray diffraction analysis. The catalytic mechanism was experimentally studied and also proposed.
- Li, Kai,Sun, Hongjian,Yang, Wenjing,Wang, Yajie,Xie, Shangqing,Li, Xiaoyan,Fuhr, Olaf,Fenske, Dieter
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- An Air-Stable N-Heterocyclic [PSiP] Pincer Iron Hydride and an Analogous Nitrogen Iron Hydride: Synthesis and Catalytic Dehydration of Primary Amides to Nitriles
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An air-stable N-heterocyclic PSiP pincer iron hydride FeH(PMe3)2(SiPh(NCH2PPh2)2C6H4) (4) was synthesized by Si-H activation of a Ph-substituted [PSiP] pincer ligand. The analogous strong electron-donating iPr-substituted [PSiP] pincer ligand was prepared and introduced into iron complex to give an iron nitrogen complex FeH(N2)(PMe3)(SiPh(NCH2PiPr2)2C6H4) (6). Both 4 and 6 showed similar high efficiency for catalytic dehydration of primary amides to nitriles. Air-stable iron hydride 4 was the best catalyst for its stabilization and convenient preparation. A diverse range of cyano compounds including aromatic and aliphatic species was obtained in moderate to excellent yields. A plausible catalytic reaction mechanism was proposed.
- Fenske, Dieter,Fuhr, Olaf,Li, Xiaoyan,Sun, Hongjian,Wang, Yajie,Xie, Shangqing,Zhang, Hua
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- Lewis acid promoted dehydration of amides to nitriles catalyzed by [PSiP]-pincer iron hydrides
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The dehydration of primary amides to their corresponding nitriles using four [PSiP]-pincer hydrido iron complexes 1–4 [(2-Ph2PC6H4)2MeSiFe(H)(PMe3)2 (1), (2-Ph2PC6H4)2HSiFe(H)(PMe3)2 (2), (2-(iPr)2PC6H4)2HSiFe(H)(PMe3)2 (3) and (2-(iPr)2PC6H4)2MeSiFe(H)(PMe3)2 (4)] as catalysts in the presence of (EtO)3SiH as dehydrating reagent was explored in the good to excellent yields. It was proved for the first time that Lewis acid could significantly promote this catalytic system under milder reaction conditions than other Lewis acid-promoted system, such as shorter reaction time or lower reaction temperature. This is also the first example that dehydration of primary amides to nitriles was catalyzed by silyl hydrido iron complexes bearing [PSiP]-pincer ligands with Lewis acid as additive. This catalytic system has good tolerance for many substituents. Among the four iron hydrides 1 is the best catalyst. The effects of substituents of the [PSiP]-pincer ligands on the catalytic activity of the iron hydrides were discussed. A catalytic reaction mechanism was proposed. Complex 4 is a new iron complex and was fully characterized. The molecular structure of 4 was determined by single crystal X-ray diffraction.
- Chang, Guoliang,Li, Xiaoyan,Zhang, Peng,Yang, Wenjing,Li, Kai,Wang, Yajie,Sun, Hongjian,Fuhr, Olaf,Fenske, Dieter
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- NHC-catalyzed silylative dehydration of primary amides to nitriles at room temperature
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Herein we report an abnormal N-heterocyclic carbene catalyzed dehydration of primary amides in the presence of a silane. This process bypasses the energy demanding 1,2-siloxane elimination step usually required for metal/silane catalyzed reactions. A detailed mechanistic cycle of this process has been proposed based on experimental evidence along with computational study.
- Ahmed, Jasimuddin,Hota, Pradip Kumar,Maji, Subir,Mandal, Swadhin K.,Rajendran, N. M.
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supporting information
p. 575 - 578
(2020/01/29)
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- Dehydration of primary amides to nitriles catalyzed by [CNC]-pincer hydrido cobalt(III) complexes
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The dehydration reactions from primary amides to nitriles were catalyzed by the [CNC]-pincer hydrido cobalt(III) complexes [(ortho-F4C6–CH[dbnd]N–C10H6)Co(III)(H)(PMe3)2] (1), [(2,5-F2C6H2–CH[dbnd]N–C10H6)Co(III)(H)(PMe3)2] (2) and [(2,4,5-F3C6H–CH[dbnd]N–C10H6)Co(III)(H)(PMe3)2] (3) as catalysts with (EtO)3SiH as an efficient reducing agent. These hydrido cobalt(III) complexes as catalysts are suitable for many substrates and have good functional group tolerance. Among the three cobalt hydrides, complex 2 is the best catalyst. This is the first hydrido cobalt complex-catalyzed dehydration of primary amides to nitriles.
- Ren, Shishuai,Wang, Yangyang,Yang, Fei,Sun, Hongjian,Li, Xiaoyan
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- Synthesis of silyl iron hydride: Via Si-H activation and its dual catalytic application in the hydrosilylation of carbonyl compounds and dehydration of benzamides
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The hydrido silyl iron complex (o-Ph2PC6H4SiMe2)Fe(PMe3)3H (2) was obtained via the activation of the Si-H bond of the bidentate silyl ligand o-Ph2P(C6H4)SiMe2H (1) by Fe(PMe3)4. 2 showed good to excellent catalytic activity in both the reduction of aldehydes/ketones and the dehydration of benzamide. In addition, with complex 2 as a catalyst, α,β-unsaturated carbonyls could be selectively reduced to the corresponding α,β-unsaturated alcohols. The mechanisms of the formation of 2 and the catalytic dehydration process are proposed and partly experimentally verified.
- Ren, Shishuai,Xie, Shangqing,Zheng, Tingting,Wang, Yangyang,Xu, Shilu,Xue, Benjing,Li, Xiaoyan,Sun, Hongjian,Fuhr, Olaf,Fenske, Dieter
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p. 4352 - 4359
(2018/03/26)
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- A process for preparing 2, 6 - difluoro phenyl nitrile of
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The invention relates to a method for preparing 2, 6-difluorobenzonitrile. The method comprises the following steps: adding an aprotic strong polar solvent, toluene, 2,6-dichlorobenzonitrile and a catalyst, controlling temperature to 110-150 DEG C, carrying out reflux and dehydration and removing methylbenzene; cooling to 90-100 DEG C and adding potassium fluoride into a reaction container; controlling reaction temperature to 150-250 DEG C, and reacting for 15-20 h; reducing temperature of the reaction container to below 50 DEG C, carrying out suction filtration to obtain a filtrate and transferring the filtrate into a rectification bottle, starting a vacuum pump with the vacuum degree being -0.1 MPa, and collecting a fraction of 105-108 DEG C so as to obtain a finished product 2, 6-difluorobenzonitrile. In comparison with the prior art, the invention has advantages as follows: reaction conditions are mild; the preparation technology is simple; and reaction yield can reach up to 98%.
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Paragraph 0033; 0034; 0035; 0036; 0037; 0038; 0039-0072
(2017/08/25)
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- Simple Copper Catalysts for the Aerobic Oxidation of Amines: Selectivity Control by the Counterion
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We describe the use of simple copper-salt catalysts in the selective aerobic oxidation of amines to nitriles or imines. These catalysts are marked by their exceptional efficiency, operate at ambient temperature and pressure, and allow the oxidation of amines without expensive ligands or additives. This study highlights the significant role counterions can play in controlling selectivity in catalytic aerobic oxidations.
- Xu, Boran,Hartigan, Elizabeth M.,Feula, Giancarlo,Huang, Zheng,Lumb, Jean-Philip,Arndtsen, Bruce A.
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supporting information
p. 15802 - 15806
(2016/12/16)
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- Efficient reductive dehydration of primary amides to nitriles catalyzed by hydrido thiophenolato iron(II) complexes under hydrosilation conditions
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The reductive dehydration of amides to nitriles under hydrosilation conditions with hydrido thiophenolato iron(II) complexes [cis-Fe(H)(SAr)(PMe3)4] (1–4) as catalysts is reported using (EtO)3SiH as an efficient reducing agent in the yields up to 93%. The merits of this catalytic system, the low catalyst loadings (2?mol%) and the amount of efficient reducing agent (EtO)3SiH, make this method more attractive.
- Xue, Benjing,Sun, Hongjian,Wang, Yan,Zheng, Tingting,Li, Xiaoyan,Fuhr, Olaf,Fenske, Dieter
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p. 148 - 150
(2016/09/07)
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- Electroorganic synthesis of nitriles via a halogen-free domino oxidation-reduction sequence
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A direct electroorganic sequence yielding nitriles from oximes in undivided cells is reported. Despite the fact that intermediate nitrile oxides might be formed, the method is viable to prepare benzonitriles without substituents ortho to the aldoxime moiety. This constant current method is easy to perform for a broad scope of substrates and employs common electrodes, such as graphite and lead.
- Hartmer, Marius F.,Waldvogel, Siegfried R.
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supporting information
p. 16346 - 16348
(2015/11/16)
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- Copper-catalyzed hydrodefluorination of fluoroarenes by copper hydride intermediates
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Breaking bad: Efficient copper-catalyzed C-F bond activation has been achieved by replacing fluorine with hydrogen. A copper hydride is proposed as the active intermediate, which proceeds through a nucleophilic attack on the fluorocarbon, as determined by experimental and theoretical results (see structure; C gray, H white, Cu light red, F light blue; distances in ?).
- Lv, Hongbin,Cai, Yuan-Bo,Zhang, Jun-Long
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supporting information
p. 3203 - 3207
(2013/04/23)
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- One-pot conversion of aromatic bromides and aromatics into aromatic nitriles via aryllithiums and their DMF adduct
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Various aromatic bromides and iodides were smoothly converted into the corresponding aromatic nitriles in good to moderate yields by the treatment with n-butyllithium and subsequently DMF, followed by treatment with molecular iodine in aq NH3. The same treatment of typical aromatics and heteroaromatics with n-butyllithium and subsequently DMF, followed by treatment with molecular iodine in aq NH3 also provided the corresponding aromatic nitriles in good yields. Moreover, the same treatment of aromatic bromides and aromatics with half amount of DIH (1,3-diiodo-5,5- dimethylhydantoin) instead of molecular iodine worked effectively to give the corresponding aromatic nitriles, respectively, in good yields. These reactions are novel and environmentally benign one-pot methods for the preparation of aromatic nitriles from aromatic bromides and aromatics, respectively, through the formation of aryllithiums and their DMF adducts.
- Ushijima, Sousuke,Moriyama, Katsuhiko,Togo, Hideo
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experimental part
p. 958 - 964
(2011/03/19)
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- Rhodococcus nitrile hydratase
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The invention relates to a Rhodococcus polynucleotide cluster which contains nucleotide sequences which encode polypeptides having the activity of a nitrile hydratase, of an auxiliary protein P15K which activates this enzyme and of a cobalt transporter, to transformed microorganisms in which the nucleotide sequences encoding these proteins are present in increased quantity, and to the use of the transformed microorganisms for preparing amides from nitriles.
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- Room-temperature nucleophilic aromatic fluorination: Experimental and theoretical studies
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(Chemical Equation Presented) Taming the reagent: The use of anhydrous tetrabutylammonium fluoride (TBAFanh) in nucleophilic aromatic substitution reactions, including variants of the selective halogen-exchange and fluorodenitration processes (see scheme), was investigated. It was shown that TBAFanh permits these reactions to be performed under surprisingly mild conditions if it is used in relatively nonpolar media.
- Sun, Haoran,DiMagno, Stephen G.
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p. 2720 - 2725
(2007/10/03)
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- Changes in the activity and selectivity of herbicides by selective fluorine substitution, taking bentranil and classic analogues as examples
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The introduction of fluorine atoms into 2-phenyl-4H-3,1-benzoxazin-4-one (bentranil) led to sweeping changes in its herbicidal properties in some cases, and 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one ('fluorobentranil') was found to be the most active compound. It can be prepared from 2-amino-6-fluoro-benzoic acid or by direct halogen exchange of 5-chloro-2-phenyl-4H-3,1-benzoxazin-4-one. The latter reaction was investigated on a pilot scale, including a high-temperature (350°C) potassium fluoride halogen exchange without solvent. When sulfolane was used as a solvent, a side reaction at 220°C - partial decomposition to a diphenylether - could be prevented by addition of a small amount of a radical scavenger. Other intermediates with a pseudohalogen substitution were obtained by side-chain chlorination of suitable methylsulfanyl benzoic acid precursors and halogen exchange. 'Fluorobentranil' shows good broad-leaf activity and selectivity on rice, cereals and maize. In a second case study, the fluoro-substituted anthranilic acids mentioned above were also found to be appropriate for synthesizing herbicidal sulfonylurea (SU) compounds via Meerwein reaction of their aniline function. Methyl 2-[({[(4-chloro-6-methoxy-2- pyrimidinyl)-amino]carbonyl}amino)sulfonyl]-6-fluorobenzoate is an example of a SU that is compatible with maize, whereas the unsubstituted Classic analogue is not selective.
- Hamprecht, Gerhard,Wuerzer, Bruno,Witschel, Matthias
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p. 117 - 122
(2007/10/03)
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- METHOD FOR PRODUCING SUBSTITUTED ORGANIC COMPOUNDS AND USE OF CATALYSTS FOR SUBSTITUTION REACTIONS
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The invention relates to a method for exchanging substituents in organic compounds, for example, chlorine for fluorine. The method involves the use of a catalyst of formulas (IVa), (IVb) or (IVc), wherein: radicals R2 to R17, independent of one another, represent hydrogen, aliphatic, cycloaliphatic, aromatic or araliphatic groups; Aq- represents a q-valent anion, and q is an integer ranging from 1 to 3.
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- Polymer electrolyte and process for producing the same
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A polymer electrolyte having, in a main chain, a structural unit represented by the following formula (1):-[Ar1-(SO2-N-(X+)-SO2-Ar2)m-SO2-N-(X+)-SO2-Ar1-O]- wherein Ar1 and Ar2 independently represent a divalent aromatic groups, m represents an integer of 0 to 3, and X+ represents an ion selected from hydrogen ion, an alkali metal ion and ammonium ion, which is excellent in proton conductivity, thermal resistance and strength. The polymer electrolyte is soluble in solvents and has excellent film forming property and recycling efficiency.
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- Method for producing compounds containing fluorine, in particular fluorobenzaldhydes and fluorobenzonitriles
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PCT No. PCT/EP98/05296 Sec. 371 Date Feb. 20, 2000 Sec. 102(e) Date Feb. 28, 2000 PCT Filed Aug. 20, 1998 PCT Pub. No. WO99/11588 PCT Pub. Date Mar. 11, 1999The invention concerns a method for producing compound containing fluorine, particularly fluorobenzaldehyde and fluorobenzonitrle, by a halogen exchange reaction with a compound of the formula I as fluorinating agent, defined in the specification, and a quatenary aminophosphonium compound of the formula III as catalyst, as defined in the specification, and in a solvent consisting of a nitro and/or sulfoxy substituted organic compound of the formula IVa and/or IVb, as defined in the specification.
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- Unexpected side products in the tetramethylammonium fluoride-dimethylsulphoxide system
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Reactions of chloro- and nitro-aromatics with low water content solutions of TMAF in DMSO can lead to complex product mixtures resulting from activation of DMSO by fluoride and the formation of DMSO-derived products. Also, the system has been shown to give hydrolysis products in addition to the well-known ethers and phenols, with carboxylic acids and benzamides being formed from the attempted fluorodenitration of substituted benzonitriles.
- Adams, Dave J.,Clark, James H.,McFarland, Heather,Nightingale, David J.
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- The effect of basicity on fluorodenitration reactions using tetramethylammonium salts
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The fluorodenitration of several nitroaromatics with tetramethylammonium salts has been found to be dependent on the basicity of the fluorinating species. Tetramethylammonium fluoride is highly basic and is capable of inducing H-D exchange in 1,3-dinitrobenzene, as well as deprotonating N,N- dimethylacetamide. Reaction of the fluoride with phthalic anhydride forms the bifluoride in situ. Tetramethylammonium bifluoride gives higher yields of the required fluoroaromatic, but slower reaction rates than the corresponding fluoride.
- Adams, Dave J.,Clark, James H.,Nightingale, David J.
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p. 7725 - 7738
(2007/10/03)
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- Tetramethylammonium hydrogendifluoride: A convenient source of nucleophilic fluoride
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Tetramethylammonium hydrogendifluoride (TMAHF2) acts as an effective fluoride source for the selective fluorination in high yields of various chloro and nitroaromatics via halogen exchange (halex) and fluorodenitration.
- Adams, David J.,Clark, James H.,Nightingale, David J.
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p. 4295 - 4301
(2007/10/03)
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- Synthesis of 2,6-Difluorobenzonitrile by Oxidative Ammonolysis of 2,6-Difluorobenzyl Chloride
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2,6-Difluorobenzonitrile was synthesized by oxidative ammonolysis of 2,6-difluorobenzyl chloride on vanadium-titanium oxide catalysts and on vanadium-titanium catalysts promoted by doping with copper oxide. The mechanism of cyano group formation was suggested.
- Suvorov,Li,Stepanova
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p. 441 - 443
(2007/10/03)
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- Process for preparing fluorobenzonitriles
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Fluorobenzonitriles and chlorofluorobenzonitriles are prepared in an advantageous manner from the corresponding chlorobenzonitriles and an alkali metal fluoride in a chlorine-fluorine exchange reaction, by catalyzing the reaction with a quaternary ammonium compound comprising at least one alkoxypolyoxyalkyl radical.
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- POLYMER-SUPPORTED AMINOPYRIDINIUM SALTS AS VERSATILE CATALYSTS FOR THE SYNTHESIS OF ARYL FLUORIDES
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Immobilized N-alkylaminopyridinium salts on divinylbenzene crosslinked polystyrene gel was reusable at least 8 times on the reaction of 4-chloronitrobenzene with anhydrous potassium fluoride in tetrahydrothiophene 1,1-dioxide to give 4-fluoronitrobenzene in high yield.The immobilized catalyst was also successfully used for a synthesis of several aryl fluorides in good yields.
- Yoshida, Yasuo,Kimura, Yoshizaku,Tomoi, Masao
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p. 7199 - 7202
(2007/10/02)
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- Aromatic radical-anions. XII. A cyclic amperometric and ESR study of the transformations of polyfluorinated benzonitrile radical-anions
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Cyclic voltamperometry and ESR spectrometry were used to study the chemical transformations of radical-anions of benzonitrile derivatives containing from two to five fluorine atoms.Two types of transformations were found to be characteristic for such species, namely, the elimination of a fluoride anion and subsequent formation of defluorination products and dimerization with the subsequent formation of fluorinated derivatives of 4,4'-dicyanodiphenyl.The facility of these processes depends significantly on the number and arrangement of the fluorine atoms in the benzene ring.The relationship between the electronic structure and reactivity of fluorinated benzonitrile radical-anions was examined.
- Efremova, N. V.,Starichenko, V. F.,Shteingarts, V. D.
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- FLUORODENITRATIONS USING TETRABUTYLAMMONIUM FLUORIDE
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Fluoroaromatics are prepared in good yield under mild conditions using the tetrabutylammonium fluoride promoted fluorodenitration of nitroaromatics.
- Clark, James H.,Smith, David K.
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p. 2233 - 2236
(2007/10/02)
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- Process for producing 2,6-difluorobenzonitrile
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A process for producing 2,6-difluorobenzonitrile comprises reducing a chloro fluorobenzonitrile selected from 3-chloro-2,6-difluorobenzonitrile, 3,5-dichloro-2,6-difluorobenzonitrile or a mixture thereof by hydrogen gas in the presence of a palladium or platinum catalyst at a temperature of 0° to 200° C.
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