79782-58-4Relevant academic research and scientific papers
Exploring Partners for the Domino α-Arylation/Michael Addition Reaction Leading to Tetrahydroisoquinolines
Solé, Daniel,Pérez-Janer, Ferran,García-Rodeja, Yago,Fernández, Israel
supporting information, p. 799 - 805 (2017/02/15)
Sulfonates, sulfonamides, and phosphonates have proven useful nucleophiles for palladium-catalyzed intramolecular α-arylation reactions leading to tetrahydroisoquinolines. Although the sulfonate α-arylation reaction can be successfully combined in a domino process with a broad range of Michael acceptors, only vinyl sulfones can be used in Michael additions when starting from sulfonamides. No domino process was developed with the phosphonate derivative. DFT calculations were carried out to gain more insights into the experimental differences observed in the reactions involving these substrates.
Synthesis of 2-(arylamino)ethyl phosphonic acids via the aza-Michael addition on diethyl vinylphosphonate
Bou Orm, Nadine,Dkhissi, Yasmina,Daniele, Stéphane,Djakovitch, Laurent
, p. 115 - 121 (2013/01/15)
A simple way of synthesising 2-(arylamino)ethyl phosphonic esters and acids via the aza-Michael addition of amines to diethyl vinylphoshonate 'on water' was developed. Various 2-(arylamino)ethyl phosphonates were initially produced through the condensation of primary and secondary amines with diethyl vinylphosphonate, focussing on those bearing one aromatic moiety, giving generally good to high yields (i.e.; 75-100%). These phosphonic esters were then hydrolysed in presence of bromomethylsilane to give quantitatively the corresponding phosphonic acids.
A practical and efficient green synthesis of β-aminophosphoryl compounds via the aza-michael reaction in water
Matveeva, Ekaterina V.,Shipov, Anatoly E.,Odinets, Irina L.
scheme or table, p. 698 - 706 (2011/06/23)
Application of water as a solvent (without any cosolvent) promotes the aza-Michael reaction of diethyl vinylphosphonate and diphenylvinylphosphine oxide with a wide range of N-nucleophiles. The solubility of the starting phosphorus substrate in water does not play a crucial role in the reaction course, decreasing to some extent the reaction rate. The reaction can be performed either at room temperature or under reflux to afford the corresponding β-aminophosphonates and β-aminophosphine oxides in excellent yields and of high purity via a simple freeze-drying isolation procedure. Application of basic catalysts makes possible the addition of weak nucleophiles such as a-amino acids and their phosphorus analogues; that is, a-aminophosphonic acids. The aqueous aza-Michael reaction allowed us to easily perform double phosphorylation of primary amines including polyamines using a reactant ratio (phosphorus substrate: amine) of 2:1. Copyright Taylor & Francis Group, LLC.
A practical and efficient green synthesis of β-aminophosphoryl compounds via the aza-Michael reaction in water
Matveeva, Ekaterina V.,Petrovskii, Pavel V.,Klemenkova, Zinaida S.,Bondarenko, Natalya A.,Odinets, Irina L.
experimental part, p. 964 - 970 (2011/11/05)
Biphasic systems room temperature imidazolium ionic liquid (RTIL)/water or water as a solvent significantly accelerate the addition of amines to vinylphosphoryl compounds hence opening green and effective synthesis of β-aminophosphoryl compounds in excellent yields over short reaction times. The application of water, being the cheapest and most non-toxic solvent, without any catalyst or co-solvent, is more advantageous as it provides a simple isolation procedure for products having high purity (> 95% according to the NMR data) via simple freeze-drying and does not require extraction with organic solvents. The solubility of the starting phosphorus substrate in water does not play crucial role in the reaction as it was demonstrated using water insoluble diphenylvinylphosphine oxide. In contrast to typical procedures, using a reactant ratio (vinylphosphoryl compound: amine) of 2:1 readily resulted in double phosphorylation of primary amines, including polyamines, in water.
Efficient synthesis of racemic β-aminophosphonates via aza-Michael reaction in water
Matveeva, Ekaterina V.,Petrovskii, Pavel V.,Odinets, Irina L.
scheme or table, p. 6129 - 6133 (2009/04/05)
Water as a solvent significantly accelerates the addition of various amines to diethyl vinylphosphonate to yield β-aminophosphonates without any catalyst compared to known procedures for such aza-Michael reactions. The products are obtained in quantitative yields and high purity over short reaction times. Using a reactant ratio (vinylphosphonate/amine) of 2:1 resulted in double phosphorylation of primary amines.
A versatile synthetic route to phosphonate-functional monomers, oligomers, silanes, and hybrid nanoparticles
Schmider, Martin,Mueh, Ekkehard,Klee, Joachim E.,Muelhaupt, Rolf
, p. 9548 - 9555 (2008/02/01)
The highly selective single Michael addition of diethyl vinylphosphonate to alkylamines represents a very versatile synthetic route affording a large variety of novel multifunctional phosphonates including aminoalkylphosphonates, phosphonate functional silanes, and phosphonate-functionalized acrylic monomers. The hydrolysis of the phosphonate group results in a phosphonic acid functional monomer which can be used as component of dental composites exhibiting improved filler - matrix interaction. The sol - gel reaction of the phosphonate- functional silanes produced novel phosphonate-functional organic/ inorganic hybrid nanoparticles with particle sizes ranging from 30 to 100 nm.
Aminobenzylation d'aldehydes phosphoniques: preparation d'acides aminoalkylphosphoniques
Fabre, Genevieve,Collignon, Noel,Savignac, Philippe
, p. 2864 - 2869 (2007/10/02)
The reaction of phosphonic aldehydes with benzylamine in presence of NaBH3CN yields benzylaminoalkylphosphonates which, submitted to catalytic hydrogenation, lead to phosphonic amino esters.When reductive amination is carried out with H2/Pd reduction and debenzylation are observed simultaneously.In the absence of reducing agent the enaminobenzylphosphonate can be isolated and N-alkylated.Hydrolysis of phosphonic amino-esters with dilute HCl gives phosphonic amino acids.The order of occurence of each operation, as well as the choice of the catalyst is discussed.
