69881-58-9Relevant academic research and scientific papers
Silica gel-mediated catalyst-free and solvent-free Michael addition of 1,3-dicarbonyl compounds to highly toxic methyl vinyl ketone without volatilization
Tanemura, Kiyoshi,Rohand, Taoufik
supporting information, (2020/06/28)
Silica gel-mediated Michael addition of 1,3-dicarbonyl compounds to methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) was carried out to give the corresponding adducts in quite excellent yields. The reactions could be carried out without any catalysts and solvents. In addition, highly toxic MVK and EVK could be employed without significant volatilization. Silica gel could be recycled five times without the decrease of the yields.
Michael addition of cyclic β-oxo ester and α-methyl cyano ester substrates with activated olefins by iron complexes of benzimidazole derived N-heterocyclic carbene ligands
Prakasham,Gangwar, Manoj Kumar,Ghosh, Prasenjit
supporting information, p. 106 - 116 (2018/02/15)
Michael addition reactions of cyclic β-oxo ester and α-methyl cyano ester substrates with acceptor activated olefins were catalyzed by iron N?heterocyclic carbene (NHC) complexes of the type, {Cp[1-benzyl-3-alkyl-benzimidazol-2-ylidene]Fe(CO)2}
Michael addition catalyzed by difluorotris(pentafluoroethyl)phosphorane
Bittner, Bozena,Koppe, Karsten,Frank, Walter,Ignat'Ev, Nikolai
supporting information, p. 22 - 27 (2015/12/30)
Difluorotris(pentafluoroethyl)phosphorane, (C2F5)3PF2, was found to be an active catalyst for the Michael addition reaction of 1,3-β-diketones or β-ketoesters (Michael donors) and linear or cyclic unsaturated ketones (Michael acceptors). The reaction proceeds under mild conditions with low catalyst loading and results in the formation of the Michael addition products in moderate to high yields. The developed protocol does not require the use of a base for the in situ generation of a carbanion (Michael donor).
Air- and water-tolerant rare earth guanidinium BINOLate complexes as practical precatalysts in multifunctional asymmetric catalysis
Robinson, Jerome R.,Fan, Xinyuan,Yadav, Jagjit,Carroll, Patrick J.,Wooten, Alfred J.,Pericàs, Miquel A.,Schelter, Eric J.,Walsh, Patrick J.
supporting information, p. 8034 - 8041 (2014/06/23)
Shibasaki's REMB catalysts (REMB; RE = Sc, Y, La-Lu; M = Li, Na, K; B = 1,1′-bi-2-naphtholate; RE/M/B = 1/3/3) are among the most enantioselective asymmetric catalysts across a broad range of mechanistically diverse reactions. However, their widespread us
PRECATALYST FOR SHIBASAKI'S RARE EARTH METAL BINOLATE CATALYSTS
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Page/Page column 12-16; 29, (2015/01/07)
Disclosed herein are schemes for the synthesis of novel hydrogen-bonded rare earth- BINOLate precatalyst complexes, the precatalysts, per se, and their application for the generation of anhydrous REMB catalysts by cation-exchange from metal halides.
Iron catalyzed Michael addition: Chloroferrate ionic liquids as efficient catalysts under microwave conditions
Vasiloiu, Maria,Gaertner, Peter,Bica, Katharina
, p. 1614 - 1619 (2012/11/07)
The iron containing ionic liquid 1-butyl-3-methylimidazolium tetrachloroferrate ([C4mim]Cl/FeCl3; χ = 0.5) proved to be an efficient catalyst for the solvent-free metal catalyzed Michael addition of ?-keto esters and enones. Due to the ionic st
Phosphine-boronates: Efficient bifunctional organocatalysts for Michael addition
Basle, Olivier,Porcel, Susana,Ladeira, Sonia,Bouhadir, Ghenwa,Bourissou, Didier
supporting information; experimental part, p. 4495 - 4497 (2012/05/31)
Phosphine-boronates R2P(o-C6H4) B(OR′)2 have been evaluated as bifunctional organocatalysts for the Michael addition of malonate pronucleophiles to methylvinylketone. The presence of the Lewis acidic boron center adjacent to phosphorus significantly improves catalytic performance. Isolation and complete characterization of a key intermediate, namely a β-phosphonium enolate, substantiate the role of the Lewis acidic moiety in the catalytic process.
Structure and catalytic activity of organopalladium(II) complexes based on 4,5-dihydro-1H-imidazol-5-one derivatives
Drabina, Pavel,Bro?, B?etislav,Padělková, Zdeňka,Sedlák, Milo?
experimental part, p. 971 - 981 (2011/03/22)
The paper describes preparation of a chiral bidentate ligand - 2-(2-bromophenyl)-4,5-dihydro-1H-imidazol-5-one, and a tridentate ligand - 2-bromo-1,3-bis(4,5-dihydro-1H-imidazol-5-on-2-yl)benzene, whose oxidative addition reaction with Pd(0) giving neutra
Asymmetric lewis acid catalysis in water: α-amino acids as effective ligands in aqueous biphasic catalytic michael additions
Aplander, Karolina,Ding, Rui,Krasavin, Mikhail,Lindstroem, V. Marcus,Wennerberg, Johan
experimental part, p. 810 - 821 (2009/07/05)
This article explores the potential of native α-amino acids as chiral ligands in aqueous asymmetric Lewis acid catalysis, employing the C-C bond forming Michael addition as a model reaction. Some insights are provided regarding the details of Yb(OTf)
Nickel complexes of nio-functionalized n-Heterocyclic carbenes as precatalysts for michael reactions in air at room temperature under the much preferred base-Free conditions
Ray, Sriparna,Shaikh, Mobin M.,Ghosh, Prasenjit
experimental part, p. 1932 - 1941 (2009/10/30)
A series of several new nickel precatalysts supported over N/O-functionalized N-heterocyclic carbenes (NHC) for the Michael reactions of B-dicarbonyl, B-keto ester, B-diester, and a-cyano ester compounds with a,B-unsaturated carbonyl compounds in air at ambient temperature under the much preferred base-free conditions are reported. Specifically, the nickel complexes, [1-(R1-aminocarbonylmethyl)-3-R2-imid-azol-2-ylidene]2Ni [R1 =2-C6H4(OMe); R2 = Me (1b), iPr (2b), CH2Ph (3b) and R1 = 2-CH2C4H3O; R2 =Me (4b), CH2Ph (5b)] carried out the highly convenient base-free Michael addition of the activated C-H compounds across a,B-unsaturated car- bonyl compounds in air at room temperature. The complexes 1b-5b were synthesized by the direct reaction of the respective imidazolium chloride salt with NiCl2-6H2Oin CH3CN in the presence of K2CO3 as a base. The exceptional stability of 1b-5b has been attributed to the deeply buried nickel-NHC CT-bonding molecular orbitals as evidenced from the density functional theory (DFT) studies. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009.
