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A MELAMINE/HF-CARBON TETRACHLORIDE LIQUID-LIQUID TWO-PHASE MIXTURE. A HIGHLY VERSATILE HYDROFLUORINATING AGENT FOR ALKENES TO FACILITATE CONTINUOUS OPERATIONS
A melamine/hydrogen fluoride-pentane or carbon tetrachloride liquid-liquid two phase mixture has been found to be a highly convenient hydrofluorinating agent for alkenes and a suitable system for the repeated use.
Yoneda, Norihiko,Nagata, Seiji,Fukuhara, Tsuyoshi,Suzuki, Akira
p. 1241 - 1242
(1984)
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Stable dialkyl ether/poly(hydrogen fluoride) complexes: Dimethyl ether/poly(hydrogen fluoride), a new, convenient, and effective fluorinating agent
The preparation, 1H, 13C, and 19F NMR structural characterization as well as with DFT-based theoretical calculations of stable dialkyl ether/poly(hydrogen fluoride) complexes are reported. Dimethyl ether/poly(hydrogen fluoride) (DMEPHF), are stable complexes of particular interest and use. The DFT calculations, that are in agreement with NMR data, suggest a cyclic poly(hydrogen fluoride) bridged structure for DMEPHF. The complex, DME-5 HF was found to be a convenient and effective new fluorinating agent with the ease. of workup and applied to several fluorination reactions, such as the hydrofluorination and bromofluorination of alkenes, and fluorination of alcohols giving good to excellent yield with high selectivity. Homologous dialkyl ether/poly(hydrogen fluoride) (R2O/[HF]n R = Et, nPr) systems are also stable and suitable for fluorination reactions.
Bucsi, Imre,Toeroek, Bela,Marco, Alfonso Iza,Rasul, Golam,Prakash, G. K. Surya,Olah, George A.
p. 7728 - 7736
(2002)
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Process For Synthesizing Fluorinated Cyclic Aliphatic Compounds
The present invention relates to a novel method for producing fluorinated cycloaliphatic compounds from the analogous aromatic compounds by hydrogenation with an Rh-carbene catalyst system.
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Paragraph 0121-0127

(2021/08/27)

Selective hydrogenation of fluorinated arenes using rhodium nanoparticles on molecularly modified silica
The production of fluorinated cyclohexane derivatives is accomplished through the selective hydrogenation of readily available fluorinated arenes using Rh nanoparticles on molecularly modified silica supports (Rh?Si-R) as highly effective and recyclable catalysts. The catalyst preparation comprises grafting non-polar molecular entities on the SiO2 surface generating a hydrophobic environment for controlled deposition of well-defined rhodium particles from a simple organometallic precursor. A broad range of fluorinated cyclohexane derivatives was shown to be accessible with excellent efficacy (0.05-0.5 mol% Rh, 10-55 bar H2, 80-100 °C, 1-2 h), including industrially relevant building blocks. Addition of CaO as scavenger for trace amounts of HF greatly improves the recyclability of the catalytic system and prevents the risks associated to the presence of HF, without compromising the activity and selectivity of the reaction.
Bordet, Alexis,Emondts, Meike,Kacem, Souha,Leitner, Walter
p. 8120 - 8126
(2020/12/28)

Hydrogenation of fluoroarenes: Direct access to all-cis-(multi)fluorinated cycloalkanes
All-cis-multifluorinated cycloalkanes exhibit intriguing electronic properties. In particular, they display extremely high dipole moments perpendicular to the aliphatic ring, making them highly desired motifs in material science. Very few such motifs have been prepared, as their syntheses require multistep sequences from diastereoselectively prefunctionalized precursors. Herein we report a synthetic strategy to access these valuable materials via the rhodium-cyclic (alkyl)(amino)carbene (CAAC)-catalyzed hydrogenation of readily available fluorinated arenes in hexane. This route enables the scalable single-step preparation of an abundance of multisubstituted and multifluorinated cycloalkanes, including all-cis-1, 2, 3, 4, 5, 6-hexafluorocyclohexane as well as cis-configured fluorinated aliphatic heterocycles.
Wiesenfeldt, Mario P.,Nairoukh, Zackaria,Li, Wei,Glorius, Frank
(2017/09/23)

METAL OXIDE CATALYZED RADIOFLUORINATION
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)

The Uranyl Cation as a Visible-Light Photocatalyst for C(sp3)?H Fluorination
The fluorination of unactivated C(sp3)?H bonds remains a desirable and challenging transformation for pharmaceutical, agricultural, and materials scientists. Previous methods for this transformation have used bench-stable fluorine atom sources; however, many still rely on the use of UV-active photocatalysts for the requisite high-energy hydrogen atom abstraction event. Uranyl nitrate hexahydrate is described as a convenient, hydrogen atom abstraction catalyst that can mediate fluorinations of certain alkanes upon activation with visible light.
West, Julian G.,Bedell, T. Aaron,Sorensen, Erik J.
supporting information
p. 8923 - 8927
(2016/07/26)

Visible light-promoted metal-free sp3-C-H fluorination
Photoexcited acetophenone can catalyze the fluorination of unactivated C(sp3)-H groups. While acetophenone, a colorless oil, only has a trace amount of absorption in the visible light region, its photoexcitation can be achieved by irradiation with light generated by a household compact fluorescent lamp (CFL). This operational simple method provides improved substrate scope for the direct incorporation of a fluorine atom into simple organic molecules. CFL-irradiation can also be used to promote certain classic UV-promoted photoreactions of colorless monoarylketones and enones/enals.
Xia, Ji-Bao,Zhu, Chen,Chen, Chuo
supporting information
p. 11701 - 11704
(2015/05/20)

A photocatalyzed aliphatic fluorination
We disclose a new approach to the catalysis of alkane fluorination employing ultraviolet light and a photosensitizer, 1,2,4,5-tetracyanobenzene (TCB). The process is efficient, mild, and operationally straightforward. We demonstrate reaction utility on a variety of substrates, from simple hydrocarbons to complex natural products. In a showcase example, we establish that the well-known photochemical rearrangement of α-santonin can be supplanted by a highly selective catalyzed fluorination. The Royal Society of Chemistry 2014.
Bloom, Steven,Knippel, James Levi,Lectka, Thomas
p. 1175 - 1178
(2014/03/21)

C-HALOGEN BOND FORMATION
Methods of halogenating a carbon containing compound having an sp3 C-H bond are provided. Methods of fluorinating a carbon containing compound comprising halogenation with Cl or Br followed by nucleophilic substitution with F are provided. Methods of direct oxidative C-H fluorination of a carbon containing compound having an sp3 C-H bond are provided. The halogenated products of the methods are provided.
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Paragraph 0139-0140; 0142-0144; 0151; 0163-0164

(2013/03/26)

Oxidative aliphatic C-H fluorination with fluoride ion catalyzed by a manganese porphyrin
Despite the growing importance of fluorinated organic compounds in drug development, there are no direct protocols for the fluorination of aliphatic C-H bonds using conveniently handled fluoride salts. We have discovered that a manganese porphyrin complex catalyzes alkyl fluorination by fluoride ion under mild conditions in conjunction with stoichiometric oxidation by iodosylbenzene. Simple alkanes, terpenoids, and even steroids were selectively fluorinated at otherwise inaccessible sites in 50 to 60% yield. Decalin was fluorinated predominantly at the C2 and C3 methylene positions. Bornyl acetate was converted to exo-5-fluoro-bornyl acetate, and 5a-androstan-17-one was fluorinated selectively in the A ring. Mechanistic analysis suggests that the regioselectivity for C-H bond cleavage is directed by an oxomanganese(V) catalytic intermediate followed by F delivery via an unusual manganese(IV) fluoride that has been isolated and structurally characterized.
Liu, Wei,Huang, Xiongyi,Groves, John T.,Cheng, Mu-Jeng,Nielsen, Robert J.,Goddard III, William A.
p. 1322 - 1325,4
(2020/08/31)

Steric crowding makes challenging Csp3 - F reductive eliminations feasible
A high-yielding fluorination of (triphos)Pt-R+ has been achieved using an array of F+ sources, with XeF2 yielding R-F in minutes. The C-F coupling proved to be a stereoretentive process that proceeds via a concerted reductive elimination from a putative dicationic Pt(IV) center. The larger the steric congestion of the (triphos)Pt-Csp3+ complexes, the more efficient the fluorination, seemingly a result of sterically accelerated C-F reductive elimination along with simultaneous deceleration of its competing processes (β-H elimination).
Zhao, Shu-Bin,Becker, Jennifer J.,Gagne, Michel R.
body text
p. 3926 - 3929
(2011/10/03)

1,1,3,3,3-Pentafluoropropene secondary amine adducts new selective fluorinating agents
Addition of secondary amine SA (dimethylamine DMA, diethylamine DEA, pyrrolidine Pyr, piperidine Pip, morpholine Mor) to pentafluoropropene PFP gives rise to generation of mixtures of two products (1-dialkylamine-1,3,3,3-tetrafluoropropene and N,N-dialkyl-1,1,3,3,3-pentafluoropropylamine) in different ratios. Those reaction mixtures, however, were found to be efficient fluorinating agents replacing hydroxyl groups in alcohols into fluorine. In general, they react with alcohols yielding corresponding fluorides, equimolar amounts of appropriate 3,3,3-trifluoropropionamide and hydrogen fluoride. Aliphatic primary alcohols including octanol and benzylic alcohol yield only alkyl fluorides. The secondary and tertiary alcohols, beside the desired fluorides, give usually considerably amount of alkenes.
Koroniak, Henryk,Walkowiak, Justyna,Grys, Krzysztof,Rajchel, Andrzej,Alty, Adam,Du Boisson, Rick
p. 1245 - 1251
(2008/09/20)

Practical and general method for direct synthesis of alkyl fluorides from alcohols under mild conditions
A variety of alcohols were treated with Ph 3P and KF in CCl 4-DMF at room temperature to afford the corresponding fluorides in very good yields. Springer-Verlag 2005.
Bandgar, Babasaheb P.,Kamble, Vinod T.,Biradar, Ankush V.
p. 1579 - 1582
(2007/10/03)

2,2-Difluoro-1,3-dimethylimidazolidine (DFI). A new fluorinating agent
2,2-Difluoro-1,3-dimethylimidazolidine (DFI) is a new deoxo-fluorinating agent that is useful for the conversion of alcohols to monofluorides, and aldehydes/ketones to gem-difluorides under mild conditions.
Hayashi, Hidetoshi,Sonoda, Hiroshi,Fukumura, Kouki,Nagata, Teruyuki
p. 1618 - 1619
(2007/10/03)

Elementalfluorine. Part 14.1 Electrophilic fluorination and nitrogen functionalisation of hydrocarbons
Selective fluorination of a range of hydrocarbons was achieved by reaction with either elemental fluorine or Selectfluor, an electrophilic fluorinating reagent of the N-F class. An electrophilic mechanism is envisaged. On prolonged reaction, the strongly acidic reaction medium that is formed upon substitution of hydrogen by fluorine when Selectfluor is used as the fluorinating reagent, promotes loss of fluoride from the initial fluorinated product. Trapping of the subsequent carbocation by the acetonitrile solvent in a Ritter type process gives overall nitrogen functionalisation of hydrocarbons. Amidation of hydrocarbons could also be achieved in a one-stage process by reaction of the hydrocarbon with fluorine and a Lewis acid, such as boron trifluoride-diethyl ether, in acetonitrile.
Chambers, Richard D.,Kenwright, Alan M.,Parsons, Mandy,Sandford, Graham,Moilliet, John S.
p. 2190 - 2197
(2007/10/03)

Nitrogen-based halogenating agents and process for preparing halogen-containing compounds
Disclosed are a fluorinating agent represented by the general formula (1): wherein R1to R4are a substituted or unsubstituted, saturated or unsaturated alkyl group or a substituted or unsubstituted aryl group, and can be the same or different; R1and R2or R3and R4can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms; or R1and R3can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms, for example: a preparation process of the fluorinating agent and a process for preparing fluorine compounds by reacting various compounds with the fluorinating agent. The invention has also disclosed that the fluorinating agent is very effective for fluorinating oxygen containing functional compounds.
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(2008/06/13)

1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine: A new selective fluorinating agent
The title compound has been prepared in 96-98% yield by the reaction of tetrafluoroethylene and dimethylamine. 1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine (1) is found to be an effective reagent for the conversion of alcohols into alkyl fluorides. Reaction of 1 and primary alcohols proceeds with high yield formation of the corresponding alkyl fluorides at elevated temperature. However, the reaction of secondary and tertiary alcohols rapidly takes place at 0-10°C, producing corresponding alkyl fluorides as major product along with some olefins.
Petrov,Swearingen,Hong,Chris Petersen
p. 25 - 31
(2007/10/03)

Electrophilic fluorination at saturated sites
Transformation of carbon-hydrogen bonds to carbonfluorine bonds at saturated secondary and tertiary carbon sites by electrophilic aliphatic substitution processes is possible using either elemental fluorine or fluorinating reagents of the N-F class.
Chambers, Richard D.,Parsons, Mandy,Sandford, Graham,Bowden, Roy
p. 959 - 960
(2007/10/03)

In situ generation and synthetic applications of anhydrous hydrogen fluoride in a solid-liquid biphasic system
The HI situ generation of anhydrous HF by reaction of solid CaF2 with H2SO4 in the presence of an organic phase containing the substrate is proposed as a simple and safe alternative to other fluorination methods. Using this method, the addition of HF to olefins to produce fluoroalkanes, the substitution of hydroxy and halide functional groups by F atoms, and the conversion of anilines to fluorobenzenes, proceed with good conversions and moderate yields. In the latter reaction, HF generation, diazotization and fluoro de-diazonization can all be carried out in one pot. Reactions can be performed at ambient temperatures and pressures. HF generation using NaF or KF as fluoride sources is less efficient due to formation of stable bifluorides. Lipophilic quaternary ammonium salts such as tetra-octylammonium bromide can be used to enhance the extraction of HF into the organic phase. The effects of solvent nature and reagent ratios are discussed.
Rothenberg, Gadi,Royz, Michael,Arrad, Onn,Sasson, Yoel
p. 1491 - 1494
(2007/10/03)

Cyclization in deiodinative fluorination
Alkyl iodides 1-5 react with xenon difluoride with loss of iodide and incorporation of fluorine. A carbocationic intermediate undergoes cyclization with an internal olefinic function.
Patrick, Timothy B.,Zhang, Likang
p. 8925 - 8928
(2007/10/03)

Hydrofluorination of Unsaturated Compounds with Solid Potassium Hydrogen Fluoride in the Presence of Silicon Tetrafluoride at Room Temperature
Hydrofluorination of unsaturated compounds proceeds by reaction with solid potassium hydrogen fluoride and silicon tetrafluoride to afford the corresponding fluorides in high yields.
Tamura, Masanori,Shibakami, Motonari,Kurosawa, Shigeru,Arimura, Takashi,Sekiya, Akira
p. 1891 - 1892
(2007/10/02)

Poly-4-vinylpyridinium poly(hydrogen fluoride): A solid hydrogen fluoride equivalent reagent
Poly-4-vinylpyridinium poly(hydrogen fluoride) (PVPHF), containing 35-60% hydrogen fluoride by weight, was prepared as a solid hydrogen fluoride equivalent reagent. PVPHF with 60% hydrogen fluoride by weight was found to be a versatile fluorinating agent for the hydrofluorination and bromofluorination of alkanes and alkynes, fluorination of alcohols as well as other fluorination reactions. Low hydrogen fluoride content PVPHF (3 equivalents of hydrogen fluoride to 1 equivalent of 4-vinylpyridine unit) was also found to be an efficient reagent for bromofluorination of alkenes in the presence of 1,3-dibromo-5,5-dimethylhydrantoin. Fluorosulfonic acid-modified PVPHF showed enhanced reactivities for the fluorination of secondary alcohols.
Olah,Li,Wang,Surya Prakash
p. 693 - 699
(2007/10/02)

Mechanistic Studies of Fluorodecarboxylation with Xenon Difluoride
The reaction of xenon difluoride with primary carboxylic acids involves a free-radical mechanism.Trifluoroacetic acid (1) decarboxylates in benzene to give (trifluoromethyl)benzene (2). 6-Hexenoic acid (3) produces a free radical in a radical clock reaction in which the kabs (25 deg C) for XeF2 was determined as 1.1 * 106 M-1 s-1.The primary radical from hexanoic acid was spin-trapped to give ESR signals diagnostic for the alkyl radical.Secondary acids were shown to proceed through a trivalent intermediate, but its exact nature was not proven.The acid 6 gave a rearranged product (7) characteristic of carbocations, whereas the diacid 8 gave difluoro compounds without stereoselectivity.The tertiary bicyclic acids 13 and 15 gave products only from solvent hydrogen abstraction strongly indicative of free radicals.
Patrick, Timothy B.,Khazaeli, Sadegh,Nadji, Sourena,Hering-Smith, Katy,Reif, Dirk
p. 705 - 708
(2007/10/02)

N-Fluorolactams: Rapid, Mild, and Regiospecific Fluorinating Agents
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Satyamurthy, N.,Bida, Gerald T.,Phelps, Michael E.,Barrio, Jorge R.
p. 3373 - 3374
(2007/10/02)

AMINOSULFUR TRIFLUORIDES: RELATIVE THERMAL STABILITY
The fluorinating reagent, DAST (diethylaminosulfur trifluoride, 1b), has the potential to decompose violently when heated and presents a hazard if not propely handled.This investigation has shown that the decomposition occurs in two steps.First, a non-ene
Messina, Patrica A.,Mange, Kevin C.,Middleton, W. J.
p. 137 - 144
(2007/10/02)

FLUORINATION OF CYCLOHEXANOLS WITH 4-MORPHOLINOSULFUR TRIFLUORIDE
In contrast to most simple alcohols, cyclohexanol has proved to be a surprisingly difficult compound to fluorinate with aminosulfur trifluorides.In the reaction of 4-morpholinosulfur trifluoride (morpho-DAST) with cyclohexanol, a correlation was found between the polarity index of the solvent, P', and the yield of fluorocyclohexane.In solvents of low polarity, there appears to be an uncharged intermediate that leads to fluorocyclohexane.In solvents of higher polarity, there appears to be a charged intermediate that gives fluorocyclohexane.By a study of the fluorination of cis- and trans-4-tert-butylcyclohexanol, conformational effects were shown to be a major factor in hindering the SN2 attack by fluoride ion on the reactive intermediate(s).
Mange, Kevin C.,Middleton, W. J.
p. 405 - 414
(2007/10/02)

FLUORINATION WITH CAESIUM FLUOROXYSULPHATE. PART XI. MILD FUNCTIONALIZATION OF SATURATED HYDROCARBONS
Several hydrocarbons reacted with caesium fluoroxysulphate in acetonitrile at 35 deg C yielding mono and disubstituted products.Fluorocyclohexane, fluorocycloheptane, and 2-exo-fluoronorbornane formed in the reactions with the corresponding hydrocarbons were accompanied by up to 15percent of other unidentified fluoro products, but their amount was strongly diminished when fluoronation was performed in the presence of nitrobenzene.Fluorination of adamantane resulted in 1-fluoro, 2-fluoro, and 1,3-difluoro substituted products, with the substitution at the tertiary carbon atom strongly predominating.The presence of nitrobenzene did not influence the rate of reaction and the product distribution when the reaction was carried out in acetonitrile, while the introduction of methanol or methanol and nitrobenzene into the reaction mixture slowed down the reaction, with no evidence of the presence of methoxy derivatives.
Stavber, Stojan,Zupan, Marko
p. 2737 - 2742
(2007/10/02)

N-HALOGENO COMPOUNDS. PART 9. N-FLUOROQUINUCLIDINIUM FLUORIDE--A NEW ELECTROPHILIC FLUORINATING AGENT
N-Fluoroquinuclidium fluoride, prepared in high yield by treatment of a cold, dilute solution of quinuclidine in trichlorofluoromethane with fluorine at low pressure in a specially designed, virtually allglass vacuum system, acts as a site-selective electrophilic fluorinating agent towards carbanionic substrates PhCF(CO2Et)2; Me2CLiNO2-->Me2CFNO2; RMgX-->RF (R = Ph, X = Br; R = c-C6H11, X = Cl); CH2CH2OCH2CH2N-CH=CH(CH23CH2-->CH2(CH2)3COCHF; PhSiCl3/F(1-) (in situ)-->PhF>.
Banks, Ronald Eric,Boisson, Richard Arthur Du,Morton, William David,Tsiliopoulos, Efthimios
p. 2805 - 2812
(2007/10/02)

Electrophilic Fluorination with N-Fluoroquinuclidinium Fluoride
N-Fluoroquinuclidinium fluoride (NFQNF), obtainable in ca. 90percent yield by direct low-temperature liquid-phase fluorination of quinuclidine, has been used to deliver 'positive' fluorine to carbanionic sites in a number of organic substrates.
Banks, R. E.,Boisson, R. A. Du,Tsiliopoulos, E.
p. 461 - 466
(2007/10/02)

Replecement of the carboxylic acid function with fluorine
Replacement of a carbonyl function by fluorine, fluorodecarboxylation, is a new process that can be accomplished by the reaction of alkanoic acids with xenon difluoride.Primary, tertiary, and benzylic acids perform best in the reaction, which is conducted at room temperature in methylene chloride or chloroform solution.A reaction mechanism is proposed in which the acid is initially converted to a fluoroxenon ester, RCO2XeF.The esters of the primary and secondary acids react by nucleophilic displacement by fluoride, as evidenced by incorporation of 18F- and no reactions common to free radicals or carbocations.The esters of the tertiary and benzylic acids react by converting to free radicals that can be further oxidized to carbocations.Thus incorporation of 18F- and racemization are observed with α-methoxy-α-trifluoromethylphenylacetic acid.Hydroxyl and amino functions inhibit the reaction.Aromatic and vinylic acids do not react.
Patrick, Timothy B.,Johri, Kamalesh K.,White, David H.,Bertrand, William S.,Mokhtar, Rodziah,et al.
p. 138 - 141
(2007/10/02)

Mechanistic aspects of the fluorination of cyclohexane and cyclohexene with acetyl hypofluorite in acetic acid
The reaction of acetyl hypofluorite in acetic acid with both cyclohexane and cyclohexene has been investigated.Analysis by GCMS and radio-HPLC, using (18)F as a tracer, revealed that apart from typical products expected from a radical reaction, several compounds originating from carbocationic intermediates were formed.On the basis of the observed products, a single-electrontransfer (SET) mechanism leading to an intermediate radical-cation is proposed.
Visser, G. W. M.,Bakker, C. N. M.,Halteren, R. W. v.,Herscheld, J. D. M.,Brinkman, G. A.,Hoekstra, A.
p. 214 - 219
(2007/10/02)

Thermically-Initiated Fluorinations at Saturated Carbon Atoms with Xenon Difluoride
The heating of several hydrocarbons with xenon difluoride at 95-120 deg C in stainless steel reactor equipped with teflon jackets resulted in mono-, di-, and trisubstituted products.
Zajc, Barbara,Zupan, Marko
p. 1659 - 1661
(2007/10/02)

HALOGEN-EXCHANGE FLUORINATION OF CYCLO AND TERTIARY ALKYL HALIDES USING Cu2O-HF-ORGANIC BASE SOLUTIONS
Cu2O-HF-Organic base (tetrahydrofuran or Et2O) solutions were used successively as a highly reactive halogen-exchange fluorination reagent for the cyclo or tertiary alkyl halides without carbon skeletal rearrangement under the mild conditions.
Yoneda, Norihiko,Fukuhara, Tsuyoshi,Nagata, Seiji,Suzuki, Akira
p. 1693 - 1694
(2007/10/02)

SELECTIVE FLUORINATIONS WITH 1-FLUORO-2-PYRIDONE
1-Fluoro-2-pyridone has been used to fluorinate selectively enamines and Grignard reagents under mild conditions.
Purrington, Suzanne T.,Jones, Walda Ann
p. 43 - 46
(2007/10/02)

MELAMINE-HYDROGEN FLUORIDE SOLUTION. A HIGHLY EFFECTIVE AND CONVENIENT HYDROFLUORINATION REAGENT OF ALKENES
A solution of 14percent (w/w) melamine in 86percent (w/w) hydrogen fluoride has been found to be stable, and more convenient and effective hydrofluorinating reagent for alkenes than those of other organic amine-hydrogen fluoride reagents.
Yoneda, Norihiko,Abe, Takafumi,Fukuhara, Tsuyoshi,Suzuki, Akira
p. 1135 - 1136
(2007/10/02)

CATALYTIC HYDROGENATION OF OLEFINS, ACETYLENES AND ARENES BY RHODIUM TRICHLORIDE AND ALIQUAT-336 UNDER PHASE TRANSFER CONDITIONS
The ion pair formed aqueous rhodium trichloride and aliquat-336 in dichloroethane catalyzes hydrogenation of a variety of unsaturated compounds.Aromatics are reduced to cyclohexane derivatives under exceedingly mild conditions.
Blum, Jochanan,Amer, Ibrahim,Zoran, Amikam,Sasson, Yoel
p. 4139 - 4142
(2007/10/02)