- 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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- O-benzenedisulfonimide as a reusable brnsted acid catalyst for hetero-michael reactions
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The hetero-Michael reactions among various oxygen, sulfur, and nitrogen nucleophiles and ,-unsaturated compounds were carried out in the presence of catalytic amounts of o-benzenedisulfonimide as Brnsted acid organocatalyst. The reaction conditions were very mild, and the yields of target products were good. The catalyst was easily recovered and purified, ready to be used in further reactions. This ability grants economic and ecological advantages. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
- Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano
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p. 758 - 767
(2013/01/15)
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- Ultrasound-assisted aza-Michael reaction in water: A green procedure
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The conjugate addition of amines to conjugated alkenes (commonly known as aza-Michael reaction) constitutes a key step for the synthesis of various complex natural products, antibiotics, α-amino alcohols and chiral auxiliaries. Ultrasound-induced addition of several amines to α, β-unsaturated ketones, esters and nitriles has been carried out very efficiently in water as well as under solvent-free conditions. No catalysts or solid supports have been used in this method. Remarkable enhancement of reaction rate has been observed in water under ultrasound-induced method. This environmentally benign procedure has provided clean formation of the products with better selectivity.
- Bandyopadhyay, Debasish,Mukherjee, Sanghamitra,Turrubiartes, Luis C.,Banik, Bimal K.
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experimental part
p. 969 - 973
(2012/05/20)
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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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- 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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- 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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- 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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- Microwave-induced aza-michael reaction in water: A remarkably simple procedure
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Microwave-induced fast addition of several amines to conjugated carbonyl compounds has been carried out in water very efficiently in the absence of any catalyst. Copyright
- Kall, Andrea,Bandyopadhyay, Debasish,Banik, Bimal K.
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experimental part
p. 1730 - 1735
(2010/07/14)
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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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- An effective aza-michael addition of aromatic amines to electron-deficient alkenes in alkaline Al2O3
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Aza-Michael addition of aromatic or aliphatic amines with various electron-deficient alkenes was performed using alkaline Al2O 3 as solid media at room temperature afforded the corresponding Michael addition products in good to excellent yields.The alkaline Al 2O3 can be easily recovered and reused.
- Ai, Xin,Wang, Xin,Liu, Jin-Ming,Ge, Ze-Mei,Cheng, Tie-Ming,Li, Run-Tao
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experimental part
p. 5373 - 5377
(2010/08/06)
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- Microwave-assisted, rapid, solvent-free aza-michael reaction by perchloric acid impregnated on silica gel
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Highly efficient solvent-free aza-Michael additions of a variety of amines to,-unsaturated carbonyl compounds under microwave-irradiation conditions catalyzed by perchloric acid impregnated on silica gel (HClO4/SiO2) is reported. The reactions are completed within 2-7min in a microwave oven to produce the corresponding adducts in excellent yields, and the catalyst can be recovered and reused.
- Singh, Surya Prakash,Kumar, T. Vijaya,Chandrasekharam,Giribabu,Reddy, P. Yella
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experimental part
p. 3982 - 3989
(2009/12/24)
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- A catalytic method for room-temperature Michael additions using 12-tungstophosphoric acid as a reusable catalyst in water
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12-Tungstophosphoric acid (H3PW12O40) has been found to be an efficient and recyclable catalyst in promoting room temperature Michael additions of amines and aryl thiols to α,β- unsaturated esters and acrylonitrile in water to afford the corresponding saturated amines in good to excellent yields. Georg Thieme Verlag Stuttgart.
- Chen, Xiang,She, Jin,Shang, Zhicai,Wu, Jun,Zhang, Peizhi
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experimental part
p. 3931 - 3936
(2009/05/26)
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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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- Bromodimethylsulfonium bromide mediated Michael addition of amines to electron deficient alkenes
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Bromodimethylsulfonium bromide has been found to be an efficient catalyst for the Michael addition of a wide variety of amines to electron deficient alkenes at room temperature. The protocol is very simple and chemoselective. Aliphatic and benzylic amines undergo conjugate addition within a very short period under solvent-free conditions and provide excellent yields of products.
- Khan, Abu T.,Parvin, Tasneem,Gazi, Sarifuddin,Choudhury, Lokman H.
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p. 3805 - 3808
(2008/02/06)
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- Tandem bis-aza-Michael addition reaction of amines in aqueous medium promoted by polystyrenesulfonic acid
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An efficient and environmentally benign tandem bis-aza-Michael addition of amines catalyzed by polystyrenesulfonic acid (PSSA) is described. This operationally simple high yielding microwave assisted synthetic protocol proceeded in water in the absence of any organic solvent.
- Polshettiwar, Vivek,Varma, Rajender S.
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p. 8735 - 8738
(2008/03/18)
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- Cellulose-supported copper(0) catalyst for aza-Michael addition
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Cellulose-supported copper(0) efficiently catalyzes the aza-Michael reaction of N-nucleophiles, such as amines and imidazoles with α,β-unsaturated compounds to produce the corresponding β-amino compounds and N-substituted imidazoles in excellent yields. The reactions are facile and the recovered catalyst is used for several cycles with consistent activity. Georg Thieme Verlag Stuttgart.
- Reddy, K. Rajender,Kumar, Nadakudity S.
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p. 2246 - 2250
(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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- Cerium(IV) ammonium nitrate (CAN) catalyzed aza-Michael addition of amines to α,β-unsaturated electrophiles
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Cerium(IV) ammonium nitrate (CAN) catalyzed facile and efficient aza-Michael addition of aromatic and aliphatic amines with α,β-unsaturated electrophiles in the absence of solvent under ultrasound irradiation.
- Duan, Zheng,Xuan, Xuejie,Li, Ting,Yang, Chenfei,Wu, Yangjie
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p. 5433 - 5436
(2007/10/03)
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- Boric acid: A novel and safe catalyst for aza-Michael reactions in water
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Boric acid efficiently catalyzes the conjugate addition of aliphatic amines to α,β-unsaturated compounds to produce β-amino compounds, with great alacrity and excellent yields, in water under mild conditions. Aromatic amines do not participate effectively in the reaction.
- Chaudhuri, Mihir K.,Hussain, Sahid,Kantam, M. Lakshmi,Neelima
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p. 8329 - 8331
(2007/10/03)
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- RuCl3 in poly(ethylene glycol): A highly efficient and recyclable catalyst for the conjugate addition of nitrogen and sulfur nucleophiles
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The 1,4-conjugate addition of primary, secondary and aromatic amines, thiols, and carbamate to α,β-unsaturated compounds mediated by a catalytic amount (0.5 mol%) of RuCl3 in poly(ethylene glycol) (PEG) provides the desired β-substituted carbonyls in high yields. In particular, we found that primary aliphatic and aromatic amines produced the single adducts as the sole products in very high yields with RuCl3-PEG. RuCl 3-PEG was readily recycled via solvent precipitation with efficient recyclability as evidenced by high yields. Its properties of low sensitivity toward moisture and oxygen, high tolerance of different functional groups, and efficient recyclability make RuCl3-PEG suitable for both laboratory and industrial scale synthesis of β-substituted carbonyls. Georg Thieme Verlag Stuttgart.
- Zhang, Huaxing,Zhang, Yuhong,Liu, Leifang,Xu, Hailiang,Wang, Yanguang
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p. 2129 - 2136
(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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- Comparative study of physical and chemical activation modes. The case of the synthesis of β-amino derivatives
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The activation of the conjugate addition of amines to α,β-ethylenic substrates is considered. Pressure (physical parameter) is a powerful tool to promote the reaction due to its effect on the nucleophilic attack on the double bond of the acrylic compound with development of zwitterionic species. Combination of pressure and lanthanide catalysis (chemical activation) is a highly efficient multiactivation mode, though it is unable to operate in strongly congested systems. Physicochemical activation by water considerably promotes the synthesis of β-amino derivatives. However in the case of acrylic esters, it is of little value since the β-aminoesters formed undergo rapid retro-Michael reactions.
- Jenner, Gerard
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p. 13557 - 13568
(2007/10/03)
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