- A New Preparation Method for the Alkylation Catalysts of Aromatic Compounds Based on Immobilized AlCl3
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Abstract: A new method for the preparation of active catalysts for the alkylation and transalkylation of aromatic compounds (benzene and toluene) based on aluminum chloride immobilized on the surface of silica gel was developed. The alkylation occurred wi
- Bykov,Belyaev
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p. 328 - 330
(2021/04/26)
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- New Heterogeneous Alkylation Catalysts Based on Niobium Pentachloride
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New active catalysts based on niobium pentachloride immobilized on the surface of silica gel or aluminum oxide for the alkylation of aromatic compounds were prepared. The reaction occurs with a high rate at room temperature. Thus, the conversion of 1-hexene in the alkylation of benzene or toluene was close to 100% only 5 min after the onset of the reaction.
- Bykov,Belyaev,Butenko
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p. 688 - 689
(2018/10/02)
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- Isobutane/2-butene alkylation catalyzed by Br?nsted-Lewis acidic ionic liquids
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The alkylation reaction of isobutane with 2-butene to yield C8-alkylates was performed using Br?nsted-Lewis acidic ionic liquids (ILs) comprising various metal chlorides (ZnCl2, FeCl2, FeCl3, CuCl2, CuCl, and AlCl3) on the anion. IL 1-(3-sulfonic acid)-propyl-3-methylimidazolium chlorozincinate [HO3S-(CH2)3-mim]Cl-ZnCl2 (x=0.67) exhibited outstanding catalytic performance, which is attributed to the appropriate acidity, the synergistic effect originating from its double acidic sites and the promoting effect of water on the formation and transfer of protons. The Lewis acidic strength of IL played an important role in improving IL catalytic performance. A 100% conversion of 2-butene with 85.8% selectivity for C8-alkylate was obtained under mild reaction conditions. The IL reusability was good because its alkyl sulfonic acid group being tethered covalently, its anion [Zn2Cl5]- inertia to the active hydrogen, and its insolubility in the product. IL [HO3S-(CH2)3-mim]Cl-ZnCl2 had potential applicability in the benzene alkylation reaction with olefins and halohydrocarbons.
- Liu, Shiwei,Tan, Shuang,Bian, Bing,Yu, Hailong,Wu, Qiong,Liu, Zhiguo,Yu, Fengli,Li, Lu,Yu, Shitao,Song, Xiuyan,Song, Zhanqian
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p. 19551 - 19559
(2018/06/11)
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- Domino Methylenation/Hydrogenation of Aldehydes and Ketones by Combining Matsubara's Reagent and Wilkinson's Catalyst
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The methylenation/hydrogenation cascade reaction of aldehydes or ketones through a domino process involving two ensuing steps in a single pot is realized. The compatibility of Matsubara's reagent and Wilkinson's complex give a combination that allows, under dihydrogen, the transformation of a carbonyl function into a methyl group. This new method is suitable to introduce an ethyl motif from aromatic and aliphatic aldehydes with total chemoselectivity and total retention of α-stereochemical purity. The developed procedure is also extended to the introduction of methyl groups from ketones.
- Maazaoui, Radhouan,Pin-Nó, María,Gervais, Kevin,Abderrahim, Raoudha,Ferreira, Franck,Perez-Luna, Alejandro,Chemla, Fabrice,Jackowski, Olivier
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supporting information
p. 5732 - 5737
(2016/12/14)
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- Use of Trifluoromethyl Groups for Catalytic Benzylation and Alkylation with Subsequent Hydrodefluorination
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The electrophilic organofluorophosphonium catalyst [(C6F5)3PF][B(C6F5)4] is shown to effect benzylation or alkylation by aryl and alkyl CF3 groups with subsequent hydrodefluorination, thus resulting in a net transformation of CF3 into CH2-aryl fragments. In the case of alkyl CF3 groups, Friedel-Crafts alkylation by the difluorocarbocation proceeded without cation rearrangement, in contrast to the corresponding reactions of alkyl monofluorides.
- Zhu, Jiangtao,Prez, Manuel,Caputo, Christopher B.,Stephan, Douglas W.
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supporting information
p. 1417 - 1421
(2016/02/14)
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- Heterogeneous Catalytic Hydroarylation of Olefins at a Nanoscopic Aluminum Chlorofluoride
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We report on hydroarylation reactions of arenes with olefins under very mild conditions catalyzed heterogeneously by aluminum chlorofluoride (ACF; AlClxF3?x, x≈0.05–0.25). The reactions of benzene and toluene with ethylene or propylene proceed with high conversions to afford various alkylated arenes. For cyclohexene and 1-hexene, the reactions require higher temperatures and the conversions are lower. ACF also catalyzes the hydroarylation of 1,3,5-trifluorobenzene and pentafluorobenzene with ethylene and propylene. The alkylations of arenes with non-fluorinated olefins resemble typical Friedel–Crafts chemistry to give rise to Markovnikov regioselectivity. The reaction of CF3CH=CH2 with benzene proceeds with anti-Markovnikov regioselectivity to give the fluorinated olefin PhCHCH=CF2 and the alkylation product PhCH2CH2CF3 as products of C?F and C?H activation.
- Calvo, Beatriz,Wuttke, Jan,Braun, Thomas,Kemnitz, Erhard
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p. 1945 - 1950
(2016/07/06)
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- Cobalt-Catalyzed Asymmetric Hydrogenation of 1,1-Diarylethenes
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Highly enantioselective cobalt-catalyzed hydrogenation of 1,1-diarylethenes was developed by using bench-stable chiral oxazoline iminopyridine-cobalt complexes as precatalysts. A unique o-chloride effect was observed to achieve high enantioselectivity. Easy removal as well as further transformations of the chloro group make this protocol a potentially useful alternative to synthesize various chiral 1,1-diarylethanes. This process can be successfully performed under 1 atm of hydrogen at room temperature on gram scale.
- Chen, Jianhui,Chen, Chenhui,Ji, Chonglei,Lu, Zhan
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supporting information
p. 1594 - 1597
(2016/05/02)
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- Extending the substrate scope of bicyclic p-oxazoline/thiazole ligands for ir-catalyzed hydrogenation of unfunctionalized olefins by introducing a biaryl phosphoroamidite group
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This study identifies a series of Ir-bicyclic phosphoroamidite-oxazoline/thiazole catalytic systems that can hydrogenate a wide range of minimally functionalized olefins (including E- and Z-tri- and disubstituted substrates, vinylsilanes, enol phosphinates, tri- and disubstituted alkenylboronic esters, and ?±,?2-unsaturated enones) in high enantioselectivities (ee values up to 99%) and conversions. The design of the new phosphoroamidite-oxazoline/thiazole ligands derives from a previous successful generation of bicyclic N-phosphane-oxazoline/thiazole ligands, by replacing the N-phosphane group with a p-acceptor biaryl phosphoroamidite moiety. A small but structurally important family of Ir-phosphoroamidite-oxazoline/thiazole precatalysts has thus been synthesized by changing the nature of the Ndonor group (either oxazoline or thiazole) and the configuration at the biaryl phosphoroamidite moiety. The substitution of the N-phosphane by a phosphoroamidite group in the bicyclic N-phosphane-oxazoline/thiazole ligands extended the range of olefins that can be successfully hydrogenated.
- Biosca, Maria,Paptchikhine, Alexander,P??mies, Oscar,Andersson, Pher G.,Di??guez, Montserrat
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supporting information
p. 3455 - 3464
(2015/03/04)
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- Iron-catalyzed allylic arylation of olefins via C(sp3)-H activation under mild conditions
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An aryl Grignard reagent in the presence of mesityl iodide converts an allylic C-H bond of a cycloalkene or an allylbenzene derivative into a C-C bond in the presence of a catalytic amount of Fe(acac)3 and a diphosphine ligand at 0 C. The stereo- and regioselectivity of the reaction, together with deuterium labeling experiments, suggest that C-H bond activation is the slow step in the catalytic cycle preceding the formation of an allyliron intermediate.
- Sekine, Masaki,Ilies, Laurean,Nakamura, Eiichi
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supporting information
p. 714 - 717
(2013/04/10)
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- A modular furanoside thioether-phosphite/phosphinite/ phosphine ligand library for asymmetric iridium-catalyzed hydrogenation of minimally functionalized olefins: Scope and limitations
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A highly modular furanoside thioether-phosphite/phosphinite/phosphine ligand library has been synthesized for the iridium-catalyzed asymmetric hydrogenation of minimally functionalized olefins. These ligands can be prepared efficiently from easily accessible D-(+)-xylose. We found that their effectiveness at transferring the chiral information in the product can be tuned by correctly choosing the ligand components. Enantioselectivities were therefore excellent (ees up to 99%) in a wide range of E- and Z-trisubstituted alkenes using 5-deoxyribofuranoside thioether-phosphite ligands. It should be pointed out that these catalysts are also very tolerant to the presence of a neighbouring polar group. For 1,1-disubstituted substrates, both enantiomers of the hydrogenation product can be obtained in high enantioselectivities simply by changing the configuration of the biaryl phosphite moiety. The asymmetric hydrogenation was also performed using propylene carbonate as solvent, which allowed the iridium catalysts to be reused while maintaining the excellent enantioselectivities. Copyright
- Coll, Mercedes,Pamies, Oscar,Dieguez, Montserrat
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p. 143 - 160
(2013/03/28)
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- A phosphite-pyridine/iridium complex library as highly selective catalysts for the hydrogenation of minimally functionalized olefins
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A modular library of readily available phosphite-pyridine ligands has been successfully applied for the first time in the iridium-catalyzed asymmetric hydrogenation of a broad range of minimally functionalized olefins. The modular ligand design has been shown to be crucial in finding highly selective catalytic systems for each substrate. Excellent enantioselectivities (ees up to 99%) have therefore been obtained in a wide range of E- and Z-trisubstituted alkenes, including more demanding triaryl-substituted olefins and dihydronaphthalenes. This good performance extends to the very challenging class of terminal disubstituted olefins, and to olefins containing neighbouring polar groups (ees up to 99%). Both enantiomers of the reduction product can be obtained in excellent enantioselectivities by simply changing the configuration of the carbon next to the phosphite moiety. The hydrogenations were also performed using propylene carbonate as solvent, which allowed the iridium catalyst to be reused and maintained the excellent Copyright
- Mazuela, Javier,Pamies, Oscar,Dieguez, Montserrat
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supporting information
p. 2569 - 2583
(2013/10/21)
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- The application of pyranoside phosphite-pyridine ligands to enantioselective Ir-catalyzed hydrogenations of highly unfunctionalized olefins
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Eight (biaryl)phosphite/pyridine ligands 1-2a-d have been prepared by the modular functionalization of positions C-2 and C-3 of two d-glucopyranoside backbones. The chiral ligands were examined in the iridium-catalyzed asymmetric hydrogenation of poorly functionalized alkenes, as a function of the relative position of the coordinating groups and the geometric properties of the biaryl phosphite moieties. Enantiomeric excesses of up to 90% were achieved in the hydrogenation of E-2-(4-methoxyphenyl)-2-butene by using 1a and 1c, which seemingly combine the beneficial effect of the phosphite at the 2-position with the matching (Rax)-configuration of their encumbered biaryl substituents. The results of the hydrogenation of more challenging substrates, such as Z-trisubstituted alkenes, alkenes with a neighboring polar group or demanding 1,1-di-substituted alkenes, generally confirmed this trend, and in some significant cases, the chiral hydrogenated products were isolated with ees of 65-79%. 2012 Elsevier Ltd.
- Margalef, Jessica,Lega, Matteo,Ruffo, Francesco,Pamies, Oscar,Dieguez, Montserrat
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experimental part
p. 945 - 951
(2012/10/07)
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- Mechanism of efficient anti-markovnikov olefin hydroarylation catalyzed by homogeneous Ir(iii) complexes
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The mechanism of the hydroarylation reaction between unactivated olefins (ethylene, propylene, and styrene) and benzene catalyzed by [(R)Ir(μ-acac-O, O,C3)-(acac-O,O)2]2 and [R-Ir(acac-O,O) 2(L)] (R = acetylacetonato, CH3, CH2CH 3, Ph, or CH2CH2Ph, and L = H2O or pyridine) Ir(iii) complexes was studied by experimental methods. The system is selective for generating the anti-Markovnikov product of linear alkylarenes (61:39 for benzene + propylene and 98:2 for benzene + styrene). The reaction mechanism was found to follow a rate law with first-order dependence on benzene and catalyst, but a non-linear dependence on olefin. 13C-labelling studies with CH313CH2-Ir-Py showed that reversible β-hydride elimination is facile, but unproductive, giving exclusively saturated alkylarene products. The migration of the 13C-label from the α to β-positions was found to be slower than the C-H activation of benzene (and thus formation of ethane and Ph-d 5-Ir-Py). Kinetic analysis under steady state conditions gave a ratio of the rate constants for CH activation and β-hydride elimination (k CH: kβ) of ~0.5. The comparable magnitude of these rates suggests a common rate determining transition state/intermediate, which has been shown previously with B3LYP density functional theory (DFT) calculations. Overall, the mechanism of hydroarylation proceeds through a series of pre-equilibrium dissociative steps involving rupture of the dinuclear species or the loss of L from Ph-Ir-L to the solvento, 16-electron species, Ph-Ir(acac-O,O)2-Sol (where Sol refers to coordinated solvent). This species then undergoes trans to cis isomerization of the acetylacetonato ligand to yield the pseudo octahedral species cis-Ph-Ir-Sol, which is followed by olefin insertion (the regioselective and rate determining step), and then activation of the C-H bond of an incoming benzene to generate the product and regenerate the catalyst.
- Bhalla, Gaurav,Bischof, Steven M.,Ganesh, Somesh K.,Liu, Xiang Yang,Jones,Borzenko, Andrey,Tenn III, William J.,Ess, Daniel H.,Hashiguchi, Brian G.,Lokare, Kapil S.,Leung, Chin Hin,Oxgaard, Jonas,Goddard III, William A.,Periana, Roy A.
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experimental part
p. 69 - 81
(2011/03/21)
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- N-Hexane activation over zeolites: Aromatic alkylation to 1-phenylhexane
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Terminal 1-phenylhexane was observed during alkylation of benzene with n-hexane over 10-membered ring zeolites at moderate temperature, whereas it was not observed when 1-hexene was the reactant. The Royal Society of Chemistry 2010.
- Danilina, Nadiya,Payrer, Elisabeth L.,Van Bokhoven, Jeroen A.
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scheme or table
p. 1509 - 1510
(2010/06/12)
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- Adaptative biaryl phosphite-oxazole and phosphite-thiazole ligands for asymmetrie Ir-catalyzed hydrogenation of alkenes
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A library of readily available phosphite-oxazole/thiazole ligands (L1a-g-L7a-g) was applied in the Ir-catalyzed asymmetric hydrogenation of several largely unfunctionalized E- and Z-trisubstituted and 1,1-disubstituted terminal alkenes. The ability of the catalysts to transfer chiral information to the product could be tuned by choosing suitable ligand components (bridgelength, the substituents in the heterocyclic ring and the alkyl backbone chain, the configuration of the ligand backbone, and the substituents/ configurations in the biaryl phosphite moiety),so that enantioselectivities could be maximized for each substrate as required. Enantioselectivities were therefore excellent (enantiomeric excess (ee) values up to >99%) for a wide range of E- and Z-trisubstituted and 1,1-disubstituted terminal alkenes. The biaryl phosphite moiety was a very advantageous ligand component in terms of substrate versatility.
- Diéguez, Montserrat,Mazuela, Javier,Paptchikhine, Alexander,Pàmies, Oscar,Andersson, Pher G.
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experimental part
p. 4567 - 4576
(2010/08/07)
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- Synthesis of enantiomerically pure allenes with central and axial chirality mediated by a remote sulfinyl group
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Enantiomerically pure 2-(p-tolylsulfinyl)benzylcopper reagents react with propargyl bromides and mesylates, affording enantiomerically pure allenes with central and axial chirality. Both regioselectivity (SN2 processes) and configuration at the
- Ruano, Jose Luis Garcia,Marcos, Vanesa,Aleman, Jose
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experimental part
p. 3339 - 3349
(2010/03/01)
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- Nitrosonium salts, NO+X- (X = B(3,5-diCF 3Ph)4- or PW12O40 3-), as electrophilic catalysts for alkene activation in arene alkylation and dimerization reactions
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It has been found that in apolar reaction media the nitrosonium cation (NO+) activated alkenes under mild conditions toward electrophilic substitution of arene substrates to yield the alkylated arene with Markovnikov orientation. In the absence of arenes the alkenes react with themselves to yield a mixture of dimeric alkenes. The nitrosonium cation can be dissolved in the reaction medium by using the tetrakis-(bis-(3,5-trifluromethyl)phenyl) borate anion, where upon the reactions occur effectively at 30 °C. Alternatively an insoluble, heterogeneous catalyst was prepared so as to yield a NO+ cation with a polyoxometalate (PW12O403-) anion. This catalyst was generally more effective and selective toward a broader range of substrates at 70 °C. Copyright
- Khenkin, Alexander M.,Neumann, Ronny
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supporting information; scheme or table
p. 11876 - 11877
(2009/02/05)
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- QUINOLINE-DERIVED AMIDE MODULATORS OF VANILLOID VR1 RECEPTOR
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This invention is directed to vanilloid receptor VR1 ligands. More particularly, this invention relates to quinoline-derived amides that are potent antagonists or agonists of VR1 which are useful for the treatment and prevention of inflammatory and other pain conditions in mammals.
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- Radical deoxygenation of tertiary alcohols via trifluoroacetates
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Trifluoroacetates of tertiary alcohols undergo deoxygenation by Ph 2SiH2 in the presence of (tBuO)2 in excellent yields of the deoxy products without affecting the stereochemistry at β-carbon.
- Kim, Joong-Gon,Cho, Dae Hyan,Jang, Doo Ok
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p. 3031 - 3033
(2007/10/03)
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- Scandium(III) triflate immobilised in ionic liquids: a novel and recyclable catalytic system for Friedel-Crafts alkylation of aromatic compounds with alkenes
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Scandium(III) triflate catalysed Friedel-Crafts alkylation of aromatic compounds with alkenes proceeded readily in the hydrophobic ionic liquid solvents based on 1,3-dialkylimidazolium salts with easy catalyst/solvent recycling, whereas these reactions did not occur in common organic solvents, water or hydrophilic ionic liquids at all.
- Song, Choong Eui,Shim, Woo Ho,Roh, Eun Joo,Choi, Jung Hoon
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p. 1695 - 1696
(2007/10/03)
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- Enhanced selectivity in the preparation of linear alkylbenzenes using hexagonal mesoporous silica supported aluminium chloride
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For decades sulphonated linear alkylbenzenes have been one of the worlds most important detergents. Industrially, their preparation involves the use of either aluminium chloride or hydrogen fluoride as catalysts in the alkylation stage of the reaction. The use of these catalysts presents severe problems in terms of both their environmental impact and their lack of selectivity towards the desired product. Solid acids, such as zeolites, can overcome these problems but at the expense of activity. It has now been discovered that by chemically supporting aluminium chloride on a MCM-41 type silica a reuseable catalyst is produced. It can be easily separated from the products and is environmentally benign. In addition, the new catalyst exhibits significant improvements in selectivity towards both the monoalkylated product and the preferred 2-phenyl isomer. Selectivity can be further increased by maximizing the relative activity of the catalytic sites situated within the pores of the catalyst.
- Price, Peter M.,Clark, James H.,Martin, Keith,Macquarrie, Duncan J.,Bastock, Tony W.
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p. 221 - 225
(2013/09/08)
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- Synthesis of (R)-2-diphenylphosphino-2′-diphenylphosphinomethyl-1,1′-binaphthyl and its use for asymmetric hydrogenation of α-alkylstyrenes
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A new chiral bisphosphine ligand ((R)-2-diphenylphosphino-2′-diphenylphosphinomethyl-1,1′-binaphthyl) was synthesized from enantiomerically pure (R)-1,1′-binaphthalene-2,2′-diol. Rhodium(I) complexes of this bisphosphine ligand have been used as catalysts for asymmetric hydrogenation of α-alkylstyrenes to give the corresponding aromatic hydrocarbons in up to 77% ee.
- Inagaki, Kohji,Ohta, Tetsuo,Nozaki, Kyoko,Takaya, Hidemasa
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p. 159 - 163
(2007/10/03)
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- Friedel-Crafts alkylation of benzene and toluene with olefinic C6 hydrocarbons and esters
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To assist our study of the reaction of toluene and other aromatic compounds with methyl oleate and other olefinic esters, benzene and toluene have been alkylated under Friedel-Crafts conditions with hex-1-ene, hex-3-ene, methyl hex-3-enoate and methyl hex-3-enedioate. The products were isolated and identified by NMR and mass spectrometric procedures.
- Black, Kenneth D.,Gunstone, Frank D.
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- Ruthenium complex-catalyzed novel transformation of alkyl formates
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The following ruthenium-catalyzed novel transformations of alkyl formates have been developed: (1) selective decarbonylation of alkyl formates to the corresponding alcohols; (2) alkylation of arenes and alkenes using alkyl formates as an alkylating reagent via decarboxylation.Also the ruthenium-catalyzed addition of alcohols to alkenes has been developed as an appendant reaction, providing an effective method for the protection of alcohols.Keywords: Ruthenium; Catalysis; Alkyl; Arene; Alkene; Alcohol
- Kondo, Teruyuki,Kajiya, Satoshi,Tantayanon, Supawan,Watanabe, Yoshihisa
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- Reaction of Raney Nickel with Alcohols
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The reaction of Raney nickel with a variety of functional groups was studied.Ethers, esters, and alkyl chlorides were found to be stable to Raney nickel in refluxing toluene; however, alcohols were found to be reactive.Primary alcohols were oxidized to aldehydes and the subsequently decarbonylated, secondary alcohols were oxidized to the corresponding ketone, and tertiary alcohols were deoxygenated.
- Krafft, Marie E.,Crooks, William J.,Zorc, Branka,Milczanowski, Stephen E.
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p. 3158 - 3163
(2007/10/02)
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- Asymmetric Conjugate Addition of Organometallic Reagents to Chiral Vinyl Sulfoximines
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The chiral vinyl sulfoximines 1 and 2 (R' = C6H5, CH3, n-Bu, C6H5CH2CH2) have been prepared; they undergo conjugate addition reactions with organometallic reagents with high asymmetric induction.These conjugate addition adducts have been converted to chiral 3-alkylalkanoic acids in high enantiomeric excess (>90percent)
- Pyne, Stephen G.
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- Equilibria of isomeric transformations and relations between thermodynamic properties of secondary alkylbenzenes
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Equilibria of mutual transformations of monoamylbenzenes and diamylbenzenes (AmB), monohexylbenzenes (HxB), monoheptylbenzenes (HpB), and monodecylbenzenes (DB) have been studied in the liquid state over the range 273 to 423 K in the presence of 3 to 9 mass per cent of AlCl3.Values of ΔfH0m and ΔfS0m for the reactions studied have been calculated from the temperature dependences of the equilibrium constants.Below are given the reactions and the corresponding values for ΔfH0m/(kJ.mol-1) and ΔfS0m/(J.K-1.mol-1): 3-AmB=2-AmB, -(0.16 +/- 0.08), (8.45 +/- 0.23); 3-HxB=2-HxB, -(0.30 +/- 0.07), (3.85 +/- 0.21); 3-HpB=2-HpB, -(0.21 +/- 0.07), (3.52 +/- 0.22); 3-DB=2-DB, -(0.23 +/- 0.14), (3.51 +/- 0.43); 4-HpB=3-HpB, (0.02 +/- 0.41), (7.57 +/- 1.29); 4-DB=3-DB, (0.09 +/- 0.41), (1.69 +/- 1.28); 5-DB=4-DB, -(0.01 +/- 0.09), (0.18 +/- 0.25).For para-to-meta transformations of diamylbenzenes the average molar reaction enthalpy is -(0.26 +/- 0.46)kJ.mol-1 and the intrinsic change of molar entropy is -(0.99 +/- 1.2)J.K-1.mol-1.It is shown that for the calculation of enthalpies of formation of secondary alkylbenzenes correlations can be used which do not take into account the position of the phenyl substituent on the aliphatic hydrocarbon chain.The calculation of enthalpies of formation of normal and secondary alkylbenzenes in the liquid state at 298.15 K is made on the basis of experimental and literature values.
- Pimerzin, A. A.,Nesterova, T. N.,Rozhnov, A. M.
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p. 641 - 648
(2007/10/02)
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- METALATION REACTIONS. VII. METALATION OF BENZYLALKYL AND β-PHENETHYLALKYL SULFIDES
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The products from the reaction between n-butyllithium and benzylalkyl and β-phenethylalkyl sulfides followed by carbonation, have been investigated by GLC/MS analysis.With benzylalkyl sulfides metalation occurs at the benzylic position, and the corresponding carboxylic acid can be isolated, but side products from Wittig like rearrangement, cleavage of the thioether bond, and aliphatic and aromatic substitution are also obtained.No benzylic metalation or Wittig-like rearrangement products are obtained from β-phenethyl sulfides: instead cleavage of the thioether bond and aliphatic and aromatic substitution occur.
- Cabiddu, S.,Floris, C.,Melis, S.,Piras, P. P.,Sotgiu, F.
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p. 149 - 156
(2007/10/02)
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- POSSIBILITY OF USING ANTIMONY PENTAFLUORIDE INTERCALATED IN GRAPHITE AS CATALYSTS FOR REACTIONS OF THE FRIEDEL-CRAFTS TYPE
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Antimony pentafluoride intercalated in graphite, produced by the reaction of gaseous antimony pentafluoride with powdered graphite in a flow-type system at 140-160 deg C, exhibits the characteristics of liquid antimony pentafluoride in the temperature range of 50-100 deg C and can be used as a catalyst for various processes of the Friedel-Crafts type.The alkylation (by 1-bromooctane, cyclohexene, cyclopentene, and acylation by capryloyl, benzoyl, and perfluorobutyryl chlorides) of benzene were realized.The oxidative characteristics of antimony pentafluoride were used for the generation of the polyatomic doubly charged sulfur cation and electrophilic reagents from polyfluorodiaryl disulfide, lead thiocyanate, and mercuric oxide and their introduction into reaction with benzene.
- Gurin, G. G.,Avramenko, A. A.,Nikonorov, Yu. I.,Yakobson, G. G.
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p. 1340 - 1345
(2007/10/02)
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