- Ruthenium (II) β-diketimine as hydroamination catalyst, crystal structure and DFT computations
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A new half-sandwich ruthenium (II) complex containing β-diketiminate ligand has been synthesized and used for hydroamination of acrylonitrile with aromatic and aliphatic amines. The catalytic activity of prepared complex was compared with a series of ruthenium complexes of β-diketiminate ligands, and the effect of electronic and steric properties of these ligands on catalytic activity of their complexes was investigated. Replacement of H atom in α position of β-diketiminate with (CF3) as an electron-withdrawing group leads to decreasing the reaction yield, and on the other hand, electron-donating group (CH3) has the opposite effect. In addition, crystal structure of [Ru(p-cymen)Cl(LH,Cl)] was determined by single X-ray crystallography. Hirshfeld surface analysis has been performed to determine the dominate interactions in molecular crystal. Furthermore, density functional, QTAIM and energy calculations have been carried out, to get the detailed insight into electronic and bonding characteristics of titled compound.
- Dindar, Sara,Nemati Kharat, Ali,Safarkoopayeh, Barzin,Abbasi, Alireza
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p. 403 - 413
(2021/04/26)
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- Bio-heterogeneous Cu(0)NC@PHA for n-aryl/alkylation at room temperature
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A pure cellulose was derived from waste fibre and it was chemically modified to a hydroxamic acid ligand. The poly(hydroxamic acid) was treated with an aqueous copper solution to afford the greenish stable five-membered copper complex; namely Cu(II)@PHA. Further, the Cu(II)@PHA was treated with a reducing agent hydrazine hydride to give brown colour cellulose supported copper nanocomplex (Cu(0)NC@PHA). The Cu(0)NC@PHA was characterised by ATR-FTIR, FE-SEM & EDS, TEM, ICP-OES, TGA, XRD and XPS analyses. The cellulose-based Cu(0)NC@PHA was used for the n-aryl/alkylation (Michael addition) reaction with a variety of α,β-unsaturated Michael acceptors to produce the corresponding n-aryl/alkyl products with an excellent yield at room temperature. The Cu(0)NC@PHA showed extraordinary stability and it was easily filtered out from the reaction mixture and may potentially recycled up to five times without loss of its original catalytic ability.
- Jian Fui, Choong,Lutfor Rahman, Md,Musta, Baba,Sani Sarjadi, Mohd,Sarkar, Shaheen M.,Xin Ting, Tang
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- Green synthesis of CuO nanoparticles using: Lantana camara flower extract and their potential catalytic activity towards the aza-Michael reaction
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Aza-Michael addition is one of the most exploited reactions in organic chemistry. It is regarded as one of the most popular and efficient methods for the creation of the carbon-nitrogen bond, which is a key feature of many bioactive molecules. Herein, we report the synthesis of CuO nanoparticles by an alkaline hydrolysis process in the presence of the flower extract of Lantana camara, an invasive weed, followed by calcination in air at 400 °C. Microscopic results indicated that the plant extract played an important role in the modulation of the size and shape of the product. In the presence of extract, porous CuO nanostructures are formed. While mostly aggregated rod-shaped CuO nanostructures are formed in the absence of extract. The products are pure and highly crystalline possessing the monoclinic phase. The CuO nanoparticles have been used as a catalyst in the aza-Michael addition reaction in aqueous medium under ultrasound vibration. The product yield is excellent and the catalyst is reusable up to the fifth cycle. The catalyst system can be extended to various substituted substrates with excellent to moderate yields.
- Chowdhury, Rakesh,Khan, Aslam,Rashid, Md. Harunar
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p. 14374 - 14385
(2020/04/23)
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- Palladium nanocatalysts in glycerol: Tuning the reactivity by effect of the stabilizer
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Palladium nanoparticles (PdNPs) prepared in neat glycerol containing TPPTS (tris(3-sulfophenyl)phosphine trisodium salt) or cinchona-based alkaloids (cinchonidine, quinidine) as capping agents, were applied as catalysts in fluoride-free Hiyama couplings and conjugate additions with the aim of evaluating the influence of the stabilizer in the catalytic reactivity. Therefore, PdNPs stabilized by phosphine favored C–C cross-couplings, whereas those containing alkaloids showed enhanced suitability for C–C homo-couplings and conjugate additions. The metal/stabilizer coordination mode, i.e. Pd–P dative bond and π-π interaction between quinoline moiety and palladium surface, is certainly key for the stabilization of different active metallic species and then promoting distinctive catalytic pathways.
- Reina, Antonio,Serrano-Maldonado, Alejandro,Teuma, Emmanuelle,Martin, Erika,Gómez, Montserrat
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- Highly efficient reduction of carbonyls, azides, and benzyl halides by NaBH4 in water catalyzed by PANF-immobilized quaternary ammonium salts
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A series of polyacrylonitrile fiber-supported quaternary ammonium salts (PANF-QAS) were prepared and applied to the catalytic reduction of aldehydes, ketones, azides, and benzyl halides in water using NaBH4 as the reducing reagent in a highly efficient, economic, and environmentally benign way. The structure-activity relationships were investigated, which showed that the catalysts made up of quaternary ammonium salts with longer alkyl chains, larger cationic radii and better lipophilicity speed up the reduction reaction to afford the products in excellent yield. Moreover, the optimized catalyst can be applied to the reduction of 1-naphthaldehyde in a continuous flow process with outstanding reactivity and recyclability.
- Du, Jianguo,Xu, Gang,Lin, Huikun,Wang, Guangwei,Tao, Minli,Zhang, Wenqin
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supporting information
p. 2726 - 2735
(2016/05/24)
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- Synthesis and catalytic activity of porous polymer containing ionic liquid structures
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A novel porous polymer containing ionic liquid (IL) structures was synthesized via quternization and condensation of 4-vinylpyridine and p-xylylene dichloride. The ionic liquid structures were incorporated in the polymeric framework and for this reason bulky IL molecules can hardly block pores and neutralize active sites. The polymer shows a high BET surface area and easily accessible active sites. Catalytically the polymer is very active in Michael additions with averaged yields over 96.0% achieved after short reaction times. The high BET surface, remarkable activity, operational simplicity, wide applicability and improved stability are the key properties of the polymer.
- Li, Junqiao,Lu, Wei,Li, Weifeng,Liang, Xuezheng
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p. 840 - 846
(2016/12/07)
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- Cyanoethylation of alcohols and amines by cesium-modified zeolite y
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Zeolite Y modified by cesium and magnesium ions was prepared by ion-exchange and impregnation methods, and its activity in the cyanoethylation of aliphatic and aromatic alcohols and amines was investigated. During the preparation of some samples, the transformation of zeolite Y into a pollucite-type phase occurred. This phase exhibited good activity in the cyanoethylation of aliphatic alcohols. The prepared solids modified by the impregnation method were more active than the ion-exchanged solids. The activities of the catalysts, in contrast to other basic solids, were scarcely affected by the presence of air or moisture. A correlation between catalyst basicity and catalytic activity is discussed. The catalysts were characterized by X-ray diffraction, volumetric nitrogen adsorption surface area measurement, and CO2 temperature-programmed desorption. Scanning electron microscopy revealed that the particles of the modified nanocatalysts were 40 nm. The reaction of acrylonitrile with linear alcohols in the presence of the catalysts was accelerated by microwave irradiation.
- Zamanian, Sara,Kharat, Ali Nemati
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p. 264 - 269
(2014/03/21)
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- Palladium nanoparticles in glycerol: A versatile catalytic system for C-X bond formation and hydrogenation processes
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Palladium nanoparticles stabilised by tris(3-sulfophenyl)phosphine trisodium salt in neat glycerol have been synthesised and fully characterised, starting from both Pd(II) and Pd(0) species. The versatility of this innovative catalytic colloidal solution has been proved by its efficient application in C-X bond formation processes (X=C, N, P, S) and C-C multiple bond hydrogenation reactions. The catalytic glycerol phase could be recycled more than ten times, preserving its activity and selectivity. The scope of each of these processes has demonstrated the power of the as-prepared catalyst, isolating the corresponding expected products in yields higher than 90%. The dual catalytic behaviour of this glycerol phase, associated to the metallic nanocatalysts used in wet medium (molecular- and surface-like behaviour), has allowed attractive applications in one-pot multi-step transformations catalysed by palladium, such as C-C coupling followed by hydrogenation, without isolation of intermediates using only one catalytic precursor. Copyright
- Chahdoura, Faouzi,Pradel, Christian,Gomez, Montserrat
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supporting information
p. 3648 - 3660
(2014/01/06)
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- Ecofriendly and efficient procedure for hetero-Michael addition reactions with an acidic ionic liquid as catalyst and reaction medium
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1-Methylimidazolium trifluoroacetate ([Hmim]-TFA) is reported as a cost-effective catalyst for a simple and environmentally benign hetero-Michael reaction. [Hmim]TFA works both as reaction medium and catalyst. The reaction is applicable to various aromatic sulfur and nitrogen nucleophiles. This method has advantages such as high yields, short reaction time, and simple workup. The catalyst could be recycled several times without any loss of activity.
- Dabiri, Minoo,Salehi, Peyman,Bahramnejad, Mahboobeh,Baghbanzadeh, Mostafa
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experimental part
p. 109 - 112
(2012/06/30)
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- Graphene oxide: An efficient and reusable carbocatalyst for aza-Michael addition of amines to activated alkenes
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Graphene oxide was found to be a highly efficient, reusable and cost-effective organocatalyst for the aza-Michael addition of amines to activated alkenes to furnish corresponding β-amino compounds in excellent yields. The Royal Society of Chemistry 2011.
- Verma, Sanny,Mungse, Harshal P.,Kumar, Neeraj,Choudhary, Shivani,Jain, Suman L.,Sain, Bir,Khatri, Om P.
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supporting information; experimental part
p. 12673 - 12675
(2012/01/05)
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- An efficient biomaterial supported bifunctional organocatalyst (ES-SO 3- C5H5NH+) for the synthesis of β-amino carbonyls
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A biomaterial supported organocatalyst, readily synthesized by the reaction of chemically modified sulfonic group containing expanded corn starch with pyridine exhibited excellent catalytic activity for the synthesis of β-amino carbonyls in excellent yields via aza-Michael addition of amines to electron deficient alkenes. A remarkable enhancement in the reaction rates was observed with the prepared bifunctional organocatalyst in comparison to the either starch grafted sulfonic acid or the corresponding homogeneous pyridinium p-toluenesulfonate.
- Verma, Sanny,Jain, Suman L.,Sain, Bir
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experimental part
p. 2314 - 2318
(2011/05/02)
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- Cesium fluoride catalyzed Aza-Michael addition reaction in aqueous media
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A green approach to the Aza-Michael addition reaction between an amine and α,β-unsaturated compounds has been achieved by conventional as well as non-conventional methods. The reaction is catalyzed by cesium fluoride (CsF) in aqueous media at ambient temperature to afford the product in excellent yield. Ultrasound irradiation has been used as a non-conventional energy source, which reduces the reaction time with improved product yield.
- Labade, Vilas B.,Pawar, Shivaji S.,Shingare, Murlidhar S.
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experimental part
p. 1055 - 1059
(2012/07/27)
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- Crown ether complex cation ionic liquids: Preparation and applications in organic reactions
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A series of crown ether complex cation ionic liquids (CECILs) were designed, synthesised and characterised by NMR spectroscopy, HRMS, thermogravimetric differential thermal analysis (TG-DTA) and elemental analysis. Their applications in various organic reactions were investigated: [15-C-5Na][OH], [15-C-5Na][OAc], [18-C-6K][OH] and [18-C-6K][OAc] (15-C-5=[15]crown-5; 18-C-6=[18]crown-6) efficiently catalysed the Michael addition of alkenes and relevant nucleophiles; [18-C-6K][OH] and [15-C-5Na][OH] effectively catalysed the Henry reaction of nitromethane and aromatic aldehydes; [18-C-6K][OH] has excellent catalytic efficiency for Knoevenagel condensation of aromatic aldehydes and malononitrile; PdCl2/[18-C-6K] 3[PO4]/K2CO3 efficaciously catalysed the Heck reaction of olefins and aromatic halides; [18-C-6K][BrO3] can be used as both oxidant and solvent in the oxidation reaction of aromatic alcohols. The CECIL catalysts [15-C-5Na][OH] (Michael addition) and [18-C-6K][OH] (Henry reaction) can be recycled and reused several times without obvious loss of activity and their recovery is very simple.
- Song, Yingying,Jing, Huanwang,Li, Bo,Bai, Dongsheng
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experimental part
p. 8731 - 8738
(2011/09/16)
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- Addition of amines and phenols to acrylonitrile derivatives catalyzed by the POCOP-type pincer complex [{κP,κC, κP-2,6-(i-Pr2PO)2C6H 3}Ni(NCMe)][OSO2CF3]
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The pincer-type complex [{κP,κC, κP-2,6-(i-Pr2PO)2C6H 3}Ni(NCMe)][OSO2CF3] (1) can serve as a precatalyst for the regioselective, anti-Markovnikov addition of nucleophiles to activated olefins. The catalyzed additions of aliphatic amines to acrylonitrile, methacrylonitrile, and crotonitrile proceed at room temperature and give quantitative yields of products resulting from the formation of C-N bonds. On the other hand, aromatic amines or alcohols are completely inert toward methacrylonitrile and crotonitrile, and much less reactive toward acrylonitrile, requiring added base, heating, and extended reaction times to give good yields. The catalytic reactivities of 1 are thought to arise from the substitutional lability of the coordinated acetonitrile that allows competitive coordination of the nitrile moiety in the olefinic substrates; this binding enhances the electrophilicity of the CC moiety, rendering them more susceptible to attack by nucleophiles. In some cases, RCN → Ni binding results in double bond isomerization/migration (allyl cyanide) or attack of nucleophiles at the nitrile moiety (cinnamonitrile and 4-cyanostyrene). Reaction of morpholine with 1 at 60 °C led to formation of the amidine derivative 2 that has been characterized by X-ray crystallography.
- Lefvre, Xavier,Durieux, Guillaume,Lesturgez, Stéphanie,Zargarian, Davit
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experimental part
p. 1 - 7
(2011/03/23)
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- Use of protease from Bacillus licheniformis as promiscuous catalyst for organic synthesis: Applications in C-C and C-N bond formation reactions
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Commercially available protease from Bacillus licheniformis has been used in different non-conventional biotransformations showing remarkable activity values. The promiscuous behaviour of this enzyme used in the cross-linked enzyme aggregates immobilized form (Alcalase-CLEA), has been successfully demonstrated for the first time in C-C bond formation processes such as aldol, Henry and Mannich reactions. On the other hand, the Bayllis-Hillman reaction between 4-nitrobenzaldehyde and methyl vinyl ketone occurred through unspecific catalysis. Interestingly, aza- Michael addition reactions of secondary amines (diethylamine, piperidine and pyrrolidine) to acrylonitrile have been also efficiently catalyzed, observing with diethylamine the most remarkable differences between the enzyme-mediated reaction and the one in the absence of catalyst. Higher reactivities were attained with pyrrolidine demonstrating the versatility of hydrolases in organic synthesis. Copyright
- Lopez-Iglesias, Maria,Busto, Eduardo,Gotor, Vicente,Gotor-Fernandez, Vicente
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supporting information; experimental part
p. 2345 - 2353
(2011/10/19)
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- Complex containing a Lewis acid and Bronsted acid for the catalytic reactions of aza-Michael addition
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The novel efficient complex catalyst containing a Lewis acid and a Bronsted acid have been prepared by the reaction of proline ion liquid and cuprous iodide. The catalyst was characterized by FT-IR techniques using pyridine as probe molecule. A fast, mild, and quantitative procedure for aza-Michael addition reactions between various amines and α,β- unsaturated carbonyl compounds and nitriles has been developed using the novel complex catalyst. The results showed that the novel catalyst owned high activities for the reactions with excellent yields within 1 min.
- Mao, Xin-Xin,Wang, Jiao,Xia, Qun-Hua,Shen, Yong-Miao
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experimental part
p. 525 - 528
(2011/10/31)
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- Hydroamination and alcoholysis of acrylonitrile promoted by the pincer complex {κP,κC,κP-2,6- (Ph2PO)2C6H3}Ni(OSO 2CF3)
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This report describes the catalytic activity of the pincer-type complex {κP,κC,κP-2,6-(Ph 2PO)2C6H3}Ni(OSO2CF 3) (1) in the anti-Markovnikov addition of aliphatic and aromatic amines and alcohols to acrylonitrile, crotonitrile, and methacrylonitrile. The influence of additives on the catalytic activities was investigated, and it was found that substoichiometric quantities of water promoted the C-N bond forming reactions catalyzed by 1, especially the reactions involving aromatic amines; in comparison, NEt3 had a less dramatic impact. The opposite pattern was observed for the alcoholysis of acrylonitrile promoted by 1: water had no beneficial effect on these reactions, while NEt3 proved to be a potent promoter. Another important difference between these reactions is that hydroamination works better with more nucleophilic amines, whereas the alcoholysis reactions work well with ArOH, CF3CH2OH, and ArCH2OH but not at all with the more nucleophilic aliphatic alcohols methanol, ethanol, and 2-propanol. Both hydroamination and alcoholysis proceed much better with acrylonitrile in comparison to its Me-substituted derivatives crotonitrile and methacrylonitrile. Under optimized conditions, precatalyst 1 promotes conjugate additions to acrylonitrile with catalytic turnover numbers of up to 100 (hydroamination) or higher (alcoholysis). Spectroscopic studies have established that the main Ni-containing species in the hydroamination reactions is a cationic adduct in which the olefinic substrate is bound to the Ni center via its nitrile moiety; this binding activates the double bond toward an outer-sphere nucleophilic attack by the amine (Michael addition). The solid-state structures of the cationic nitrile adducts [{κP, κC,κP-2,6-(Ph2PO)2C 6H3}Ni(NCR)][OSO2CF3] (R = Me (2a), CH2CH2N(H)Ph (2e)), which can be regarded as model complexes for the species involved in the hydroamination catalysis, have been elucidated. Also reported are the solid-state structures of the charge-neutral compound {κP,κC,κP-2,6-(i- Pr2PO)2C6H3}Ni(OSO 2CF3) and an octahedral Ni(II) species resulting from the aerobic/hydrolytic oxidation of 1.
- Salah, Abderrahmen B.,Offenstein, Caroline,Zargarian, Davit
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experimental part
p. 5352 - 5364
(2011/12/13)
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- Solid sodium stannate as a high-efficiency superbase catalyst for anti-Markovnikov hydroamination and hydroalkoxylation of electron-deficient olefins under mild conditions
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A solid superbase with H- above 26.5 has been obtained through thermal treatment of sodium stannate hydrate. It was found to be an efficient catalyst for anti-Markovnikov hydroamination and hydroalkoxylation of electron-deficient olefins under mild conditions.
- Zhang, Shuguo,Wei, Yudan,Yin, Shuangfeng,Au, Chak-Tong
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p. 712 - 716
(2013/01/09)
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- POSITIVE RESIST COMPOSITION AND PATTERNING PROCESS
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A positive resist composition comprises (A) a resin component which becomes soluble in an alkaline developer under the action of an acid and (B) an acid generator. The resin (A) is a polymer comprising recurring units containing a non-leaving hydroxyl group represented by formula (1) wherein R1 is H, methyl or trifluoromethyl, X is a single bond or methylene, m is 1 or 2, and the hydroxyl group attaches to a secondary carbon atom. The composition is improved in resolution when processed by lithography.
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- Aqueous aza-michael reaction of conjugated alkenes: Toward spermine
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An aqueous aza-Michael reaction is efficiently achieved with excellent conversions without any additives. The method works very well on a molar scale with selectively for aliphatic amines. An intermediate for spermine is also made by this green process.
- Joshi, Jigar H.,Saiyed, Akeel S.,Bedekar, Ashutosh V.
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experimental part
p. 2857 - 2863
(2010/11/18)
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- Aza-michael addition of amines to α,β-unsaturated compounds using molecular iodine as catalyst
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Aza-Michael adducts are obtained in very good yields by the conjugate addition of aliphatic amines to α,β-unsaturated compounds using molecular iodine as catalyst in dichloromethane at room temperature. Aromatic amines were found to be reactive under reflux in toluene.
- Borah, Kalyan Jyoti,Phukan, Mridula,Borah, Ruli
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experimental part
p. 2830 - 2836
(2010/11/02)
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- Silicon tetrachloride catalyzed aza-michael addition of amines to conjugated alkenes under solvent-free conditions
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The efficient and very simple conjugate addition of aromatic and aliphatic amines to α,β-unsaturated carbonyl compounds under solvent-free conditions in the presence of catalytic amount of silicon tetrachloride is reported. The reaction of aryl and alkyl amines with different Michael acceptors gave the corresponding Michael adducts with simple catalyst and good to excellent yields. Georg Thieme Verlag Stuttgart New York.
- Azizi, Najmedin,Baghi, Roya,Ghafuri, Hossein,Bolourtchian, Mohammad,Hashemi, Mohammad
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experimental part
p. 379 - 382
(2010/04/03)
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- Iodine-alumina catalyzed Aza- michael addition under solvent free conditions
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An efficient aza-Michael addition of amines to a variety of activated olefins was carried out under solvent free conditions using iodine-alumina as a catalyst at room temperature or under microwave irradiation (in case of solid) in high yield. 2009 Bentham Science Publishers Ltd.
- Saikia, Monmi,Kakati, Dwipen,Joseph, Maria Stalin,Sarma, Jadab Chandra
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experimental part
p. 654 - 658
(2010/06/15)
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- STABILIZATION OF HYDROXYLAMINE CONTAINING SOLUTIONS AND METHOD FOR THEIR PREPARATION
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The invention relates to the use of amidoximes for prevention of or stabilization of hydroxylamine compounds against undesired decomposition.
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Page/Page column 13
(2009/05/28)
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- Michael additions of primary and secondary amines to acrylonitrile catalyzed by lipases
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The present Letter details our findings on the lipase-catalyzed Michael reactions between primary or secondary amines and acrylonitrile. Several lipases were evaluated, and good results were obtained leading to the formation of Michael adducts in shorter reaction times than the uncatalyzed reactions.
- Souza, Rodrigo O.M.A. de,Matos, Lilian M.C.,Gon?alves, Karen M.,Costa, Ingrid C.R.,Babics, Ivelize,Leite, Selma G.F.,Oestreicher,Antunes
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experimental part
p. 2017 - 2018
(2009/07/05)
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- N-donor ligand as catalyst: A simple Aza-Michael addition reaction in aqueous media
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(Chemical Equation Presented) A novel approach for the Aza-Michael addition reactions between various amines and α,β-unsaturated esters, nitriles and ketones using N-donor Ligand catalyst (3 mol %) is described. The reactions are carried out in aqueous media at an ambient temperature to afford the products in excellent yields.
- Pawar, Shivaji S.,Dekhane, Deepak V.,Shingare, Murlidhar S.,Thore, Shivaji N.
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experimental part
p. 1869 - 1873
(2009/06/18)
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- Imidazolium-based polymer supported gadolinium triflate as a heterogeneous recyclable Lewis acid catalyst for Michael additions
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A heterogeneous Lewis acid catalytic system has been developed by incorporating gadolinium triflate on to poly[styrene-co-(1-((4-vinylphenyl)methyl)-3-methylimidazolium) tetrafluoroborate] (1-Gd(OTf)3), and the catalytic activity of this system has been examined for Michael additions of amines and thiols to α,β-unsaturated esters and acrylonitrile. The reactions proceed in moderate to excellent yields in the presence of catalytic system 1-Gd(OTf)3. The catalytic system could be efficiently recycled and reused.
- Alleti, Ramesh,Oh, Woon Su,Perambuduru, Meher,Ramana,Prakash Reddy
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p. 3466 - 3470
(2008/09/21)
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- Palladium-catalyzed C-N bond activation: The synthesis of β-amino acid derivatives from triethylamine and acrylates
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In the palladium-catalyzed reaction of acrylates, C-N bond activation and acetalization occurred under different conditions. Described herein is a highly efficient palladium-catalyzed C-N bond activation reaction and subsequent new C-N bond formation to directly construct β-amino acids from triethylamine and acrylate esters in isolated yields of up to 95%. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
- Zou, Bo,Jiang, Huan-Feng,Wang, Zhao-Yang
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p. 4600 - 4604
(2008/02/12)
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- Samarium(III) triflate catalyzed conjugate addition of amines to electron-deficient alkenes
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Amines undergo smooth nucleophilic addition to α,β-unsaturated compounds in the presence of a catalytic amount of samarium(III) triflate at ambient temperature to produce the corresponding β-amino compounds in excellent yields. This method is simple, convenient, and works efficiently under mild conditions. Georg Thieme Verlag Stuttgart.
- Yadav,Ramesh Reddy,Gopal Rao,Narsaiah,Subba Reddy
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p. 3447 - 3450
(2008/09/19)
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- Significant rate acceleration of the aza-Michael reaction in water
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The addition of amines to conjugated alkenes has been carried out in water at room temperature very efficiently without any catalyst. Significant rate acceleration of this reaction is observed in water compared to organic solvents.
- Ranu, Brindaban C.,Banerjee, Subhash
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p. 141 - 143
(2007/10/03)
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- Zirconium(IV) chloride-mediated chemoselective conjugate addition of aliphatic amines to α,β-ethylenic compounds
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Zirconium chloride efficiently catalyzes the conjugate addition of a variety of aliphatic amines to α,β-unsaturated ester, nitriles, and ketones to give the corresponding β-amino derivatives in excellent yields under mild reaction conditions. Aromatic amines do not participate in this transformation. Copyright Taylor & Francis Group, LLC.
- Meshram,Lakshindra,Reddy,Sadashiv,Yadav
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p. 795 - 801
(2007/10/03)
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- ZrOCl2·8H2O on montmorillonite K10 accelerated conjugate addition of amines to α,β-unsaturated alkenes under solvent-free conditions
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At room temperature, ZrOCl2·8H2O on montmorillonite K10 efficiently catalyzes conjugate addition of amines to a variety of conjugated alkenes such as α,β-unsaturated carbonyl compounds, carboxylic esters, nitriles and amides under solvent-free conditions. The catalyst can be recycled for subsequent reactions without any appreciable loss of efficiency.
- Hashemi, Mohammed M.,Eftekhari-Sis, Bagher,Abdollahifar, Amir,Khalili, Behzad
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p. 672 - 677
(2007/10/03)
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- Addition of secondary amines to α,β-unsaturated carbonyl compounds and nitrites by using microstructured reactors
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Several additions of amines to α,β-unsaturated carbonyl compounds (Michael additions) were performed in a continuous-flow microstructured reactor rig and compared to the respective batch reaction. Dimethylamine/diethylamine/piperidine and acrylic acid ethyl ester/acrylonitrile were employed as two sets of reactants, giving six reactions. Some of these reactions are highly exothermal. Using the traditional batch procedure the olefin must be added quite slowly to the diluted amine to ensure temperature control and safe operation; especially this is necessary for the addition of dimethylamine (40 mass % aqueous solution) to acrylonitrile. Good yields (>85%) are achieved in this way; however, processing time is very long (17-25 h). To reveal the intrinsic kinetic potential and thus to accelerate these reactions, the reactants were mixed in a continuous-flow microstructured reactor rig which allows rapid mixing and efficient removal of the reaction heat. In this way, reaction time was decreased to a few seconds up to about half an hour, which is a change by 2 orders of magnitude. While the yields achieved with the continuous-flow microstructured reactor rig matched those for the batch procedure, the space-time yields for the microflow processing are much higher, in the best case by a factor of about 650.
- Loewe,Hessel,Lob,Hubbard
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p. 1144 - 1152
(2012/12/23)
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- Novel tertiary (meth)acrylates having lactone structure, polymers, resist compositions and patterning process
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Novel tertiary (meth)acrylate compounds having a lactone structure are polymerizable into polymers having improved transparency, especially at the exposure wavelength of an excimer laser and dry etching resistance. Resist compositions comprising the polymers are sensitive to high-energy radiation, have a high resolution, and lend themselves to micropatterning with electron beams or deep-UV rays.
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-
- Transition-metal-based Lewis acid catalysis of aza-type Michael additions of amines to α,β-unsaturated electrophiles in water
-
Several transition-metal-based Lewis acid catalysts, especially FeCl 3 · 7 H2O, CrCl3 · 6 H 2O, and SnCl4 · 4 H2O, were shown to be highly effective for aza-type Michael reactions between electrophilic α,β-unsaturated compounds and both aliphatic and aromatic amines in aqueous solution. Advantages of the new protocol include 1) high-yielding reactions that can be conducted at ambient temperature; 2) the use of inexpensive, stable transition-metal salts as catalysts; and 3) plain H 2O as an environmentally benign solvent.
- Xu, Li-Wen,Li, Lyi,Xia, Chun-Gu
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p. 1522 - 1526
(2007/10/03)
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- A green, ionic liquid and quaternary ammonium salt-catalyzed aza-Michael reaction of α,β-ethylenic compounds with amines in water
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The first environmentally benign, highly efficient conjugate addition of aliphatic amines to α,β-unsaturated compounds catalysed by simple quaternary ammonium salts and ionic liquids in the green solvent, water, is described.
- Xu, Li-Wen,Li, Jing-Wei,Zhou, Shao-Lin,Xia, Chun-Gu
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p. 183 - 184
(2007/10/03)
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- LiClO4 accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions
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Several primary and secondary amines were added to α,β- unsaturated esters, nitriles, amides, and ketones to give the corresponding saturated amines mediated by solid lithium perchlorate under solvent-free and environmentally friendly conditions at room temperature.
- Azizi, Najmedin,Saidi, Mohammad R.
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p. 383 - 387
(2007/10/03)
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- Lipase catalysed Michael addition of secondary amines to acrylonitrile
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A new enzymatic process is described. Different preparations of lipase B from Candida antarctica are able to catalyse Michael-type addition of secondary amines to acrylonitrile. This new reaction widens the applicability of these biocatalysts in organic synthesis.
- Torre, Oliver,Alfonso, Ignacio,Gotor, Vicente
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p. 1724 - 1725
(2007/10/03)
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- Amine compounds, resist compositions and patterning process
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Amine compounds having a cyano group are useful in resist compositions for preventing a resist film from thinning and also for enhancing the resolution and focus margin of resist.
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- Efficient Copper-Catalyzed Chemo Selective Conjugate Addition of Aliphatic Amines to α,β-Unsaturated Compounds in Water
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The first environmentally benign, highly efficient, conjugate addition of aliphatic amines to α,β-unsaturated compounds catalyzed by simple copper salts in the green solvent, water is described.
- Xu, Li-Wen,Li, Jing-Wei,Xia, Chun-Gu,Zhou, Shao-Lin,Hu, Xiao-Xue
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p. 2425 - 2427
(2007/10/03)
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- 5-HT3 receptor agonist, novel thiazole derivative and intermediate thereof
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A 5-HT3 receptor against containing a thiazole derivative as the effective ingredient is provided and is represented by the Formula (I): STR1 wherein the A ring is substituted or unsubstituted and represents a benzene or a heterocyclic ring with one or two heteroatoms; one of L1 or L2 represents a single bond and the other is non-existent or represents an alkylene or alkenylene group; R represents: STR2
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- THE S- AND N-ADDITION OF THE COMPLEXES OF AMINES WITH SULFUR DIOXIDE TO ELECTROPHILIC ALKENES
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The addition of the complexes of amines with sulfur dioxide to acrylonitrile, methacrylonitrile, and crotononitrile was relized.The reactions of acrylonitrile with CH3NH2 -> SO2 and C2H5NH2 -> SO2 complexes take place with the formation of N-alkyl-2-cyanoethanesulfonamides (S-addition of the complexes at the double bond).The electrophilic alkenes react with (CH3)2NH -> SO2 and (C2H5)2NH -> SO2 to form complexes of the substituted β-aminonitriles with sulfur dioxide (N-addition of the complexes at the double bond).
- Bodrikov, I. V.,Krasnov, V. L.,Samodurov, I. N.,Kazantsev, O. A.
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p. 923 - 928
(2007/10/02)
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- Palladium-Catalyzed Synthesis of 2,4-Dienoic Acid Derivatives from Vinylic Halides
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A wide variety of vinylic bromides and iodides have been coupled with acrylic, methacrylic, crotonic, and maleic esters and in some cases with the free acids, nitriles, and amides.In general, good yields of the 2,4-dienoic acid derivatives were obtained.The stereochemistry of the products was determined and the factors influencing the stereoselec-tivity of the reaction were studied.
- Kim, Jin-Il,Patel, Babu A.,Heck, Richard F.
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p. 1067 - 1073
(2007/10/02)
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