- A simple route to 6- and 7-fluoro-substituted naphthalene-1-carboxylic acids
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A simple one-pot method for the synthesis of 6-fluoro- and 6,7-difluoro-1-naphthoic acid is described. 6-Fluoro-1-naphthoic acid can be converted into 7-fluoro-1-naphthoic acid in three straightforward steps.
- Krülle, Thomas M.,Barba, Oscar,Davis, Susan H.,Dawson, Graham,Procter, Martin J.,Staroske, Thomas,Thomas, Gerard H.
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Read Online
- Method for pipeline continuous fluorination with fluorine salt as fluorine source
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The method comprises the following steps: dissolving a fluorine salt in an aqueous polar aprotic solvent as reaction liquid A, dissolving an aryl (heterocyclic) chloride in a polar aprotic solvent as reaction liquid B, and reacting a polar aprotic solvent in the reaction liquid A with a polar aprotic solvent of the reaction liquid B. The reaction medium consisting of the preheated reaction liquid A and the preheated reaction liquid B enters the reaction coil for a fluorination reaction, and the resulting product from the reaction coil is subjected to post-treatment to obtain the product. The method has the characteristics of no need of adding a phase transfer catalyst, continuous production, low production cost and the like.
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Paragraph 0056-0061; 0094-009; 0097
(2021/10/27)
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- Fluorination of arylboronic esters enabled by bismuth redox catalysis
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Bismuth catalysis has traditionally relied on the Lewis acidic properties of the element in a fixed oxidation state. In this paper, we report a series of bismuth complexes that can undergo oxidative addition, reductive elimination, and transmetallation in a manner akin to transition metals. Rational ligand optimization featuring a sulfoximine moiety produced an active catalyst for the fluorination of aryl boronic esters through a bismuth (III)/bismuth (V) redox cycle. Crystallographic characterization of the different bismuth species involved, together with a mechanistic investigation of the carbonfluorine bond-forming event, identified the crucial features that were combined to implement the full catalytic cycle.
- Planas, Oriol,Wang, Feng,Leutzsch, Markus,Cornella, Josep
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p. 313 - 317
(2020/01/28)
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- Hypervalent Iodine(III)-Catalyzed Balz–Schiemann Fluorination under Mild Conditions
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An unprecedented hypervalent iodine(III) catalyzed Balz–Schiemann reaction is described. In the presence of a hypervalent iodine compound, the fluorination reaction proceeds under mild conditions (25–60 °C), and features a wide substrate scope and good functional-group compatibility.
- Xing, Bo,Ni, Chuanfa,Hu, Jinbo
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supporting information
p. 9896 - 9900
(2018/07/31)
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- Application of trivalent iodine compounds as catalysts in Bal-Schiemann reaction
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The invention discloses an application of trivalent iodine compounds shown in formula I and/or II in the description and used as catalysts in Bal-Schiemann reaction. The trivalent iodine compounds areused as the catalysts in the Bal-Schiemann reaction, so that the Bal-Schiemann reaction can be conducted at room temperature or near room temperature when a thermochemical method is used, and the reaction has mild reaction conditions, wide substrate use range and short reaction time, and is safe and easy to operate, products are easy to separate, and raw materials are simple and low in toxicity.
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Paragraph 0053; 0058
(2018/10/19)
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- Ni-Catalyzed Stannylation of Aryl Esters via C?O Bond Cleavage
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A Ni-catalyzed stannylation of aryl esters with air- and moisture-insensitive silylstannyl reagents via Csp2 ?O cleavage is described. This protocol is characterized by its wide scope, including challenging combinations, thus enabling access to versatile building blocks and orthogonal C?heteroatom bond formations.
- Gu, Yiting,Martín, Rúben
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p. 3187 - 3190
(2017/03/17)
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- Nucleophilic deoxyfluorination of phenols via aryl fluorosulfonate intermediates
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This report describes a method for the deoxyfluorination of phenols with sulfuryl fluoride (SO2F2) and tetramethylammonium fluoride (NMe4F) via aryl fluorosulfonate (ArOFs) intermediates. We first demonstrate that the reaction of ArOFs with NMe4F proceeds under mild conditions (often at room temperature) to afford a broad range of electronically diverse and functional group-rich aryl fluoride products. This transformation was then translated to a one-pot conversion of phenols to aryl fluorides using the combination of SO2F2 and NMe4F. Ab initio calculations suggest that carbon-fluorine bond formation proceeds via a concerted transition state rather than a discrete Meisenheimer intermediate.
- Schimler, Sydonie D.,Cismesia, Megan A.,Hanley, Patrick S.,Froese, Robert D.J.,Jansma, Matthew J.,Bland, Douglas C.,Sanford, Melanie S.
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p. 1452 - 1455
(2017/02/10)
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- METAL OXIDE CATALYZED RADIOFLUORINATION
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Inter alia, the first titania-catalyzed [18F]-radiofluorination in highly aqueous medium is provided. In embodiments, the method utilizes titanium dioxide, 1 : 1 acetonitrile- thexyl alcohol solvent mixture and tetrabutylammonium bicarbonate as a base. Radiolabeling may be directly performed with aqueous [18F]fluoride without the need for drying/azeotroping step, which reduces radiosynthesis time while keeping high fluoride conversion. The general applicability of the synthetic strategy to the synthesis of the wide range of PET probes from tosylated precursors is demonstrated.
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Paragraph 0111; 0113
(2016/02/28)
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- Synthesis of aryl fluorides from potassium aryltrifluoroborates and selectfluor mediated by iron(III) chloride
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The synthesis of fluorinated arenes by the iron-mediated fluorination of potassium aryltrifluoroborates with Selectfluor and potassium fluoride is described. The fluorination reaction uses commercially available reagents and without requiring the addition
- Dubbaka, Srinivas Reddy,Gadde, Satyanarayana,Narreddula, Venkateswara Reddy
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p. 854 - 860
(2015/03/14)
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- Silver-mediated fluorination of potassium aryltrifluoroborates with Selectfluor Dedicated to Professor Andrea Vasella on the occasion of his 71st birthday
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A simple and practical procedure for the silver-mediated fluorination of aryl- and heteroaryltrifluoroborates with electrophilic fluorine from Selectfluor and LiOH·H2O is presented. The reaction procedure is simple and easy to set up, the process produces fluorinated arenes and heteroarenes in good to excellent yields and a wide range of electronically and structurally diverse substrates are tolerated.
- Dubbaka, Srinivas Reddy,Narreddula, Venkateswara Reddy,Gadde, Satyanarayana,Mathew, Thresen
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p. 9676 - 9681
(2015/01/08)
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- Cu-catalyzed fluorination of diaryliodonium salts with KF
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A mild Cu-catalyzed nucleophilic fluorination of unsymmetrical diaryliodonium salts with KF is described. This protocol preferentially fluorinates the smaller aromatic ligand on iodine(III). The reaction exhibits a broad substrate scope and proceeds with high chemoselectivity and functional group tolerance. DFT calculations implicate a CuI/CuIII catalytic cycle.
- Ichiishi, Naoko,Canty, Allan J.,Yates, Brian F.,Sanford, Melanie S.
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p. 5134 - 5137
(2013/10/22)
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- Mild copper-mediated fluorination of aryl stannanes and aryl trifluoroborates
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This communication describes a mild copper-mediated fluorination of aryl stannanes and aryl trifluoroborates with N-fluoro-2,4,6-trimethylpyridinium triflate. This protocol demonstrates broad substrate scope and functional group tolerance, and does not require the use of any noble metal additives. The reaction is proposed to proceed via an arylcopper(III) fluoride intermediate.
- Ye, Yingda,Sanford, Melanie S.
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supporting information
p. 4648 - 4651
(2013/05/09)
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- Metal-Catalyzed Carbon-Fluorine Bond Formation
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One aspect of the invention relates to a metal-catalyzed conversion of aryl halides and sulfonates to the corresponding aryl fluorides. Another aspect of the invention relates to a metal-catalyzed conversion of heteroaryl halides and sulfonates to the corresponding heteroaryl fluorides. Another aspect of the invention relates to a metal-catalyzed conversion of vinyl halides and sulfonates to the corresponding vinyl fluorides. In certain embodiments, simple fluoride sources, such as AgF and CsF, are used. In certain embodiments, the transformations tolerate a wide range of functional groups, allowing for introduction of fluorine atoms into highly functionalized organic molecules.
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Page/Page column 18
(2011/02/18)
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- Fluorination of Bi- and polycyclic aromatic hydrocarbons with N-fluorobis(phenylsulfonyl)amine in the absence of solvent
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Reactions of N-fluorobis(phenylsulfonyl)amine with naphthalene, 1-methylnaphthalene, phenanthrene, anthracene, and pyrene without solvent were investigated. Sometimes the fluorination of aromatic compounds with N-fluorobis(phenylsulfonyl)amine without solvent proceeded more selectively than at the use of fluorinating reagents in solution.
- Borodkin,Elanov,Shubin
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experimental part
p. 1317 - 1322
(2011/01/04)
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- Process for the Synthesis of Highly Active Binary Metal Fluoride as a Fluorinating Agent for Aromatics
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The subject invention relates to a process for the synthesis of highly active binary metal fluoride system for the fluorination of aromatic compounds. Fluorinated aromatic compounds are valuable synthons for the chemical synthesis of pharmaceutical drugs and novel polymers. Fluorobenzene is used to control carbon content in steel manufacturing, is an intermediate for pharmaceuticals, pesticides and other organic compounds. Fluorobenzene is typically produced by the reaction of aniline and sodium nitrite in the presence of hydrogen fluoride. The present invention relates to a process for the synthesis of highly active binary metal fluoride system consists of copper (II) fluoride and aluminum (III) fluoride for the fluorination of aromatic compounds in gas phase and recycling of the reagent, in situ, using O2 and HF.
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Page/Page column 6
(2010/02/17)
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- Highly reactive and regenerable fluorinating agent for oxidative fluorination of aromatics
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A newly synthesized copper aluminum fluoride of nominal composition CuAl2F8 exhibits excellent reactivity towards direct oxidative fluorination of aromatic compounds, as well as fluorodechlorination of chloroaromatics. The spent CuAl2F8 reagent can be regenerated by treatment with O2 and HF, and the fluorination process has been demonstrated to retain high conversions through 20 reaction cycles. The main advantages of this new process are safety, minimal waste, and potentially low cost.
- Janmanchi, Krishna Murthy,Dolbier Jr., William R.
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p. 349 - 354
(2013/01/03)
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- Photochemical generation and reactivity of naphthyl cations: cine substitution
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The photochemical solvolyses of naphthalen-1-yl(phenyl)-iodonium tetrafluoroborate and naphthalen-2-yl(phenyl)-iodonium tetrafluoroborate in methanol regiospecifically yield the naphthalen-1- and -2-yl ethers but afford scrambled 1- and 2-phenylnaphthalene Friedel-Crafts products. It is demonstrated that singlet naphthyl cations account for the formation of the naphthyl ethers, but that the cine substitution is most likely to be due to the intermediacy of triplet naphthyl cations. According to the experiments reported here, the singlet naphthyl cations are lower in energy than their triplet isomers. High-level MO calculations for the cations in methanol support this finding. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
- Slegt, Micha,Minne, Floor,Zuilhof, Han,Overkleeft, Hermen S.,Lodder, Gerrit
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p. 5353 - 5363
(2008/03/14)
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- Processes for preparing fluoroarenes from haloarenes
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Processes for preparing fluoroarenes are provided. The processes include contacting a compound having an unactivated aryl group with a source of fluoride or bifluoride in the presence of a transition metal a ligand.
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Page/Page column 3
(2008/06/13)
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- DIHYDROIMIDAZOTHIAZOLE DERIVATIVES
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Compounds of formula (I): or pharmaceutically acceptable salts thereof, exhibit 5-HT1A agonism in addition to noradrenaline reuptake inhibition and optionally also 5-HT reuptake inhibition are useful for the treatment of obesity.
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Page/Page column 54
(2008/06/13)
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- The stereochemical course of the generation and interception of a six-membered cyclic allene: 3δ2-1H-naphthalene (2,3-didehydro-1,2-dihydronaphthalene)
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The bromofluorocarbene adduct rac-1 of indene, possessing the fluorine atom at the endo position, is a useful substrate for the generation of the isonaphthalene 4 by the Doering-Moore-Skattebol reaction. By resolution of rac-1, an enantiomerically pure precursor of a six-membered cyclic allene was obtained for the first time. The treatment of (+)- or (-)-1, dissolved in 2,5-dimethyl-, 2-tert-butyl-5-methyl-, or 2,5-bis-(tert-butyl)furan, with methyllithium gave rise to the [4+2] cycloadducts 6 of 4 to the furans. It was shown by means of HPLC on Chiralcel OD that the formation of 6 proceeded with about 40 % ee, and that this value was independent of the type and concentration of the furan, and the reaction temperature. The absolute configurations of the enantiomers 1, as well as those of the enantiomers 6, were determined by simulation of the CD spectra by quantum chemical methods and by the comparison of them with the experimental spectra. In the case of (+)-1, the reliability of this procedure was checked by X-ray crystal structure analysis. On the basis of these results, a model is proposed for the steric course of the reaction sequence, leading from a pure enantiomer 1 to the 70:30 mixtures of the product enantiomers 6. The use of indene as trapping reagent for 4 furnished the [2+2] cycloadduct 15. For the preparation of rac-15, the particularly simple one-pot procedure was employed, in which indene, tetra-bromomethane, and methyllithium were combined and in which the dibromocarbene adduct 2 of indene serves as precursor of 4. Compound 2 could not be isolated, but was characterised by low-temperature 1H NMR spectra. The conversion of (+)- or (-)-1 into 4 in the presence of indene afforded 15 only with a very low enantioselectivity. The constitutions and the relative configurations of 15 as well as the compounds 8 and 16, which resulted from thermolysis of the cycloadducts 6b and 15, respectively, were elucidated by X-ray crystal diffraction. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Christl, Manfred,Braun, Martin,Fischer, Hartmut,Groetsch, Stefan,Mueller, Germar,Leusser, Dirk,Deuerlein, Stephan,Stalke, Dietmar,Arnone, Mario,Engels, Bernd
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p. 5045 - 5058
(2007/10/03)
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- First application of ionic liquids in electrophilic fluorination of arenes; Selectfluor (F-TEDA-BF4) for "green" fluorination
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The NF fluorinating agent F-TEDA-BF4 dication salt (Selectfluor) 1 dissolves in imidazolium-based ionic liquids [emim][OTf] 7, [emim][BF4] 8, [bmim][PF6] 9 and [bmim][BF4] 10 (assisted by sonication), providing a convenient medium for fluorination of arenes under essentially acid-free conditions in a simple set-up (no volatile solvent; simple extraction of the aromatics without aqueous work-up), from which the ionic liquid can be easily recycled and reused. Comparative studies in [emim][OTf] 7 with anisole as substrate show that 1 is superior to NFTh-BF4 (Accufluor) 2 and that the N-fluoropyridinium salt NFPy-B2F7 4 is least effective. The scope of the reaction has been surveyed. Substrate selectivity (k mesitylene: k durene = 10) measured in competitive experiments in 7 is clearly indicative of a conventional polar mechanism. Substrate selectivity measured without the ionic liquid in MeCN solvent is also indicative of a polar mechanism but exhibits lower magnitude (k mesitylene: kdurene = 6). Addition of dicyclohexano-24-crown-8 to the fluorination reaction mixture (1 and anisole) in 7 reduced the conversion but did not change the isomer distribution. AM1 minimization was used to model the complexation of 1 with this crown. With reactive aromatics optimal fluorination yields in ionic liquids (using 1 equivalent of the NF reagent) are around 50% (higher for naphthalene). A key control experiment suggests that the free base (produced upon transfer-fluorination) could complex to unreacted 1 (generating a bulky dimer complex which may be ineffective for fluorine transfer) in competition to N-protonation.
- Laali, Kenneth K.,Borodkin, Gennady I.
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p. 953 - 957
(2007/10/03)
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- Electrophilic fluorination of aromatics with selectfluor and trifluoromethanesulfonic acid 1
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1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane bis (tetrafluoroborate) [Selectfluor F-TEDA-BF4 (TEDA = triethylenediamine)] in the presence of trifluoromethanesulfonic acid has been found to be a very effective reagent system for the direct electrophilic fluorination of a wide variety of aromatic compounds under mild reaction conditions to the corresponding fluoroaromatics in good to excellent yields.
- Shamma, Tatyana,Buchholz, Herwig,Prakash, G. K. Surya,Olah, George A.
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p. 207 - 210
(2007/10/03)
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- Solvent effects in the fluorination of aromatic molecules with 'F-TEDA-BF4'
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The type of functionalization of an aromatic molecule achieved with 1-chloro-4-fluoro-1,4-diazobicyclo-(2,2,2)octane bis-tetrafluoroborate, 'F-TEDA-BF4', in trifluoroacetic acid depends on its structure: naphthalene and phenanthrene gave fluorinated products, anthracene gave the trifluoroacetate, while an addition process occurred with 9-methoxy-phenanthrene in methanol, and an addition-elimination process in trifluoroacetic acid. - Keywords: Solvent effects; Fluorination; Aromate molecules; F-TEDA-BF4; Structural effects; Addition processes
- Zupan, Marko,Iskra, Jernej,Stavber, Stojan
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- Aryl fluoride syntheses involving reactions of aryllead triacetates with boron trifluoride-diethyl ether complex
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Aryllead(IV) triacetates react at room temperature with BF3.Et2O to give the corresponding aryl fluoride in moderate to good yields; triarylboroxines, electron rich aryltrimethylsilanes and some arenes, which yield aryllead triacetates in acid catalysed reactions with lead tetraacetate, are converted directly into aryl fluorides when stirred with lead tetraacetate in BF3.Et2O. An investigation of the mechanism of the fluoro-deplumbation reaction indicates that it probably proceeds by acid catalysed heterolytic cleavage of the C-Pb bond to produce an aryl cation.
- De Meio,Morgan,Pinhey
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p. 8129 - 8138
(2007/10/02)
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- A new synthesis of aryl fluorides: The reaction of caesium fluoroxysulfate with arylboronic acids and derivatives
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The ipso fluorination of arylboronic acids and some derivatives with caesium fluoroxysulfate has been developed. The reaction proceeds with the wide range of functionalised aromatics and is strongly solvent dependent.
- Diorazio,Widdowson,Clough
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p. 8073 - 8088
(2007/10/02)
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- The thermal conversions of 6,6-difluorobicyclo[3.1.0]hex-2-enes to fluorobenzenes. An interesting dichotomy of mechanisms
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A kinetic study of the thermal, dehydrofluorinative aromatization reactions of two ostensibly-similar 6,6-difluorobicyclo[3.1.0]hex-2-ene systems led to the conclusion that drastically different mechanisms operate for the two reactions. Activation parameters, solvent effects, kinetic isotope effects, isotope labelling experiments and observation of reactive intermediates all contributed to the conclusion that the reaction of 6,6-difluorobicyclo[3.1.0]hex-2-ene, 1, proceeds via a homolytic hydrogen-shift rearrangement, while the reaction of 2,3-benzo-6,6-difluorobicyclo[3.1.0]hex-2-ene, 6, proceeds via a solvolytic mechanism involving rate-determining carbocation formation.
- Dolbier Jr.,Keaffaber,Burkholder,Koroniak,Pradhan
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p. 9649 - 9660
(2007/10/02)
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- REACTION OF FLUOROCHLOROCARBENE WITH CYCLOPENTADIENE, INDENE, AND THEIR ALKYL DERIVATIVES BY PHASE TRANSFER CATALYSIS
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Fluorochlorocarbene, generated from CHCl2F using phase transfer catalysis, reacts with indene, cyclopentadiene, and their alkyl derivatives to form 2-fluoronaphthalenes or fluorobenzenes in 9-60percent yield.Reactions proceed through formation of unstable fluorochlorocyclopropanes, which rearrange selectively independently of their stereochemical configuration into the corresponding aromatic fluorides with elimination of HCl.
- Volchkov, N. V.,Zabolotskikh, A. V.,Ignatenko, A. V.,Nefedov, O. M.
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p. 1458 - 1461
(2007/10/02)
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- Aryl Fluorides from the Reaction of Boron Trifluoride with Aryl-lead(IV) Triacetates, which may be generated in situ from Aryltrimethylsilanes, Triarylboroxines, and Arenes
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Aryl-lead(IV) triacetates react at room temperature with BF3*Et2O to give the corresponding aryl fluoride in moderate to good yields; triarylboroxines, electron-rich aryltrimethylsilanes, and some arenes, which yield aryl-lead(IV) triacetates in acid catalysed reactions with lead tetra-acetate, may be converted directly into aryl fluorides when stirred with lead tetra-acetate in BF3*Et2O.
- Meio, Giuseppe V. De,Pinhey, John T.
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p. 1065 - 1066
(2007/10/02)
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- Generation of Radical-cations from Naphthalene and Some Derivatives, both by Photoionization and Reaction with SO4-.: Formation and Reactions Studied by Laser Flash Photolysis
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Radical-cations from naphthalene and some derivatives have been generated in aqueous acetonitrile both by direct photolysis (with λ 248 nm light via biphotonic ionization) and via reaction with SO4-..The radical-cation reacts rapidly with the parent substrate (k ca. 1E8 dm3 mol-1 s-1) and with nucleophiles (e. g. with N3- k = 4.2*1E9 dm3 mol-1 s-1 or with water, k 4*1E4 s-1 ).The radical-cation from 1-naphthylethanoic acid undergoes rapid decarboxylation (k 5*1E5 s-1).The radical cations from 4-methyl- and 4-methoxy-phenylethanoic acid also rapidly decarboxylate to yield the corresponding benzyl radicals.
- Steenken, Steen,Warren, Cathryn J.,Gilbert, Bruce C.
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p. 335 - 342
(2007/10/02)
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- A Computerised Least Square Method for Determination of Stability Constants of 1:1 Molecular Complexes and Chemical Shift of Pure Complexes from Nuclear Magnetic Resonance Data
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A computerised method utilising nuclear magnetic resonance data has been developed for the determination of stability constants of 1:1 molecular complexes.It is based on the principle of least squares in which the coefficients are adjusted under a constraint with the help of Lagrange's method of undetermined multipliers.The method utilises the complete expression for equilibrium constant and is mathematically rigorous, straightforward, non-iterative and requires very little computer time.
- Seal, B. K.,Mukherjee, A. K.
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p. 413 - 415
(2007/10/02)
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- THE REACTION OF FLUOROXYSULFATE, SO4F(1-), WITH AROMATIC COMPOUNDS: CATLYSIS BY ACIDS
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The effects of the acid catalysts HF, H2SO4, BF3, CF3SO3H, FSO3H, and SbF5*FSO3H on the reactions of CsSO4F with toluene, nitrobenzene and naphthalene in CH3CN have been studied.The catalysts in general accelerate reaction and enhance yields of ring-fluorinated products.Efficacity roughly parallels H0 of the acids, though H2SO4 is more effective than stronger acids for fluorination of naphthalene.Combined room temperature yields of fluorine-substituted products are as much as 45-50 percent for toluene and naphthalene and up to 30 percent for nitrobenzene.The predominant products are o-fluorotoluene, 1-fluoronaphthalene, and m-fluoronitrobenzene.With naphthalene the isomer selectivity is considerably less than in the absence of catalyst.Low yields ( = 10 percent) of monomeric oxygenated products are obtained, along with considerable oxygen- and fluorine-containing dimers and higher polymers.The results are interpreted in terms of acid-catalyzed electrophilic fluorination or oxygenation, followed by further fluorination and/or freeradical-induced oxidative coupling of the oxygenated products.
- Appelman, Evan H.,Basile, Louis J.,Hayatsu, Ryoichi
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p. 189 - 198
(2007/10/02)
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- Reaction of Fluoroxysulfate with Aromatic Compounds
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The fluoroxysulfate ion, SO4F-, substitutes fluorine on aromatic compounds in acetonitrile solution at room temperature.However, benzylfluoride is the principal product from toluene.Other products are also formed, particularly in the case of the less reactive aromatic substrates.Product distributions and relative reactivities are interpreted in terms of an initial electophilic attack that can be followed by free-radical side reactions.
- Ip, Dominic P.,Arthur, Carol D.,Winans, Randall E.,Appelman, Evan H.
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p. 1964 - 1968
(2007/10/02)
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- ROOM TEMPERATURE FLUORINATION OF AROMATIC MOLECULES WITH CESIUM FLUOROXYSULPHATE
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Room-temperature fluorination of benzene with cesium fluoroxysulphate in the presence of boron trifluoride as catalyst resulted in the formation of fluorobenzene, while reaction with naphthalene gave 1-fluoro and 2-fluoronaphthalene in the ratio 5:1, the overall yield being between 38 and 42percent.The fluorination of phenanthrene and pyrene should be carried out at higher dilution and needs no catalyst.Phenanthrene gave 9-fluorophenanthrene and 9,9-difluoro-10-keto-9,10-dihydrophenanthrene in the ratio 1:6 in a yield of about 70percent, while pyrene gave 1-fluoro and 4-fluoropyrene in the ratio 7.5:1.
- Stavber, Stojan,Zupan, Marko
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p. 597 - 600
(2007/10/02)
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