111136-34-6Relevant academic research and scientific papers
Creation of monomeric La complexes on apatite surfaces and their application as heterogeneous catalysts for Michael reactions
Mori, Kohsuke,Oshiba, Michitaka,Hara, Takayoshi,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi
, p. 44 - 52 (2006)
Using a cation-exchange method, an equimolar substitution of La 3+ for Ca2+ occurred by the treatment of stoichiometric hydroxyapatite (HAP: Ca10(PO4)6(OH) 2) with an aqueous solution of La(OTf)3, affording a monomeric hydroxyapatite-bound La complex (LaHAP). Physicochemical characterization by means of XRD, XPS, IR, and La K-edge XAFS analyses proved that a monomeric La3+ phosphate complex was generated on its surface. Such monomeric La3+ species function as an efficient heterogeneous catalyst for the Michael reaction of 1,3-dicarbonyls with enones under aqueous or solvent-free conditions. The work-up procedure is straightforward and the spent catalyst could be recycled without any loss of the catalytic activity. Further application to an asymmetric version was also investigated using various apatite catalysts modified with chiral organic ligands. Enantioselectivity was found to depend on the chiral ligand, solvent, and rare earth metal triflate precursor (RE(OTf)3) for the reaction of methyl 1-oxoindan-2- carboxylate with methyl vinyl ketone. Under optimized reaction conditions, a monomeric fluoroapatite-bound La complex catalyst modified with (R,R)-tartaric acid (TA-LaFAP) provided the Michael adduct quantitatively in up to 60% ee. the Royal Society of Chemistry the Centre National de la Recherche Scientifique 2006.
Merrifield resin-C6H4CH2N 3P(MeNCH2CH2)3N: An efficient reusable catalyst for room-temperature 1,4-addition reactions and a more convenient synthesis of its precursor P(MeNCH
Venkat Reddy, Chinta Reddy,Verkade, John G.
, p. 3093 - 3096 (2007)
(Chemical Equation Presented) 1,4-Additions to a variety of Michael acceptors with a wide variety of donors were efficiently catalyzed at room temperature by the title reusable Merrifield resin-supported catalyst. Advantages of this catalyst include a sim
Copper(II) triflate immobilized in [bmim]BF4 ionic liquid: An efficient reaction medium for Michael addition of β-ketoesters to acceptor-activated alkenes
Yadav,Reddy,Baishya, Gakul,Venkat Narsaiah
, p. 102 - 103 (2005)
1,3-Dicarbonyl compounds undergo smooth conjugate addition to α,β-unsaturated ketones in the presence of 10 mol % copper(II) triflate immobilized in air and moisture stable [bmim]BF4 ionic liquid under extremely mild conditions to afford the co
Highly efficient phosphazene base-catalyzed Michael addition of β-ketoesters in water
Bensa, David,Brunel, Jean-Michel,Buono, Gérard,Rodriguez, Jean
, p. 715 - 717 (2001)
Michael addition of various β-ketoesters with several Michael acceptors in water containing 10 mol% of N-phenyltris(dimethylamino)iminophosphorane results in high yield conversion to the corresponding adducts.
Pentacoordinate organosilicate-catalyzed Michael addition of β-keto esters to 3-buten-2-one
Tateiwa, Jun-Ichi,Hosomi, Akira
, p. 1445 - 1448 (2001)
The Michael addition of β-keto esters to 3-buten-2-one (methyl vinyl ketone, MVK) in the presence of a pentacoordinate organosilicate was investigated. Ethyl 2-oxo-1-cyclohexanecarboxylate reacted with MVK in the presence of potassium bis(1,2-benzenediola
Michael addition catalyzed by difluorotris(pentafluoroethyl)phosphorane
Bittner, Bozena,Koppe, Karsten,Frank, Walter,Ignat'Ev, Nikolai
, p. 22 - 27 (2016)
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).
P-BEMP: A new efficient and commercially available user-friendly and recyclable heterogeneous organocatalyst for the Michael addition of 1,3-dicarbonyl compounds
Bensa, David,Constantieux, Thierry,Rodriguez, Jean
, p. 923 - 927 (2004)
Michael addition of 1,3-dicarbonyls with various Michael acceptors has been found to be catalyzed by commercially available, user-friendly and recyclable N-phenyl-tris(dimethylamino)iminophosphorane immobilized on polystyrene resin (P-BEMP). The reaction
Iron catalyzed Michael addition: Chloroferrate ionic liquids as efficient catalysts under microwave conditions
Vasiloiu, Maria,Gaertner, Peter,Bica, Katharina
, p. 1614 - 1619 (2012)
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
Supported phenolates as efficient catalysts of the Michael reaction
Macquarrie, Duncan J.
, p. 4125 - 4128 (1998)
Simple, heterogeneous base catalysts based on supported phenolates can be easily prepared and are very active and selective in the Michael reaction.
α-amino acid induced rate acceleration in aqueous biphasic Lewis acid catalyzed Michael addition reactions
Aplander, Karolina,Ding, Rui,Lindstrom, U. Marcus,Wennerberg, Johan,Schultz, Sara
, p. 4543 - 4546 (2007)
It's as easy as ABC: α-Amino acids may become very important tools in the development of economical and environmentally friendly aqueous biphasic catalysis. Alanine accelerated an Yb(OTf)3-catalyzed Michael addition by a factor of 138. The solubilizing and stabilizing properties of alanine allowed the metal catalyst to be "heterogenized" in the aqueous phase and recycled multiple times without appreciable loss of activity.
