26040-15-3Relevant academic research and scientific papers
Synthesis of α-aminophosphonates using solvate ionic liquids
Eyckens, Daniel J.,Henderson, Luke C.
, p. 27900 - 27904 (2017)
A range of α-aminophosphonates were accessed in high yields and very rapidly, using solvate ionic liquids as the reaction media. Reactions typically required less than 10 minutes to go to completion and precipitation of these products into water excludes the use of traditional work up procedures, giving the products in very high crude purity. Excellent functional group tolerance for both the aldehyde and amine reaction partners was observed, and a range of bis-aminophosphonates derived from aromatic diamines were also accessed in high yield and purity.
Synthesis of α-aminophosphonates using a mesoporous silica catalyst produced from sugarcane bagasse ash
Boza, Arthur F.,Kupfer, Vicente L.,Oliveira, Aline R.,Radovanovic, Eduardo,Rinaldi, Andrelson W.,Meneguin, Joziane G.,Domingues, Nelson L. C.,Moisés, Murilo P.,Favaro, Silvia L.
, p. 23981 - 23986 (2016/03/15)
A new green synthesis route is proposed for obtaining a mesoporous material using sugarcane bagasse ash (SCBA) as the silica source. The material obtained was denoted by SBA-16 and its mesostructure was characterized by low-angle X-ray diffraction (XRD), Fourier transform infrared (FTIR) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM) and nitrogen adsorption techniques. Sulfonic acid groups were introduced to the as-synthesized material, resulting in an acid catalyst denoted by SBA-16/SO3H. The catalytic activities of SBA-16 and SBA-16/SO3H were investigated in Kabachnik-Fields reactions, where α-aminophosphonate compounds were produced. The results show that both products can be considered as promising catalysts, where SBA-16/SO3H showed a slightly better performance than SBA-16.
Zinc Di(l-prolinate)-Mediated Synthesis of α-Aminophosphonates under Mild Conditions
De Oliveira, Aline R.,Katla, Ramesh,Rocha, Mariana P. D.,Albuquerque, Tábata B.,Da Silva, Caren D. G.,Kupfer, Vicente L.,Rinaldi, Andrelson W.,Domingues, Nelson Luís Campos
, p. 4489 - 4494 (2016/12/16)
An efficient method has been developed for the preparation of α-aminophosphonates by using zinc di(l-prolinate) as a catalyst under mild reaction conditions. The method has the advantages of high yields, short reaction times, and easy workup conditions.
A new, efficient and recyclable [Ce(l-Pro)]2(Oxa) heterogeneous catalyst used in the Kabachnik-Fields reaction
Da Silva, Caren D. G.,Oliveira, Aline R.,Rocha, Mariana P. D.,Katla, Ramesh,Botero, Eriton Rodrigo,Da Silva, érica C.,Domingues, Nelson Luís C.
, p. 27213 - 27219 (2016/03/25)
Herein we introduce a new catalyst for the Kabachnik-Fields reaction, [Ce(l-Pro)]2(Oxa), using a very accessible, simple and efficient methodology for α-aminophosphonate synthesis using an aromatic aldehyde, an aromatic amine and diphenyl phosphite. This procedure was developed using a low catalyst loading of cerium(iii) prolinate and it has allowed for the recycling of the catalyst.
SUBSTITUENT EFFECTS ON THE 31P, 13C, AND 1H NMR CHEMICAL SHIFTS OF SUBSTITUTED DIPHENYL 1-PHENYLAMINO-1-PHENYLMETHANEPHOSPHONATES AND THEIR ANIONS
Smith, Scott J.,Zimmer, Hans,Fluck, Ekkehard,Fischer, Peter
, p. 105 - 120 (2007/10/02)
For a series of thirty-five novel diphenyl 1-phenylamino-1-phenylmethanephosphonates, substituted in the meta and para positions on the anilino and/or aryl ring, 31P chemical shifts show a good linear correlation with Hammett ?n and Taft ?0 parameters, the 31P nucleus being better shielded in the case of electron withdrawing substituents.The same pattern is observed for the phosphonate anions, except when para phenyl substituents can interact with the phosphorus atom by direct resonance.This inverse relationship is due to a field effect of the substituent dipole which polarizes ?-electron clouds in the molecule.A corresponding shift in ?-electron density is likewise observed for 13C resonances of the two diastereotopic phenoxy groups, the phenylamino and phenyl moieties.Vicinal CH-NH coupling is shown to be dependent on the rate of NH proton exchange as influenced by resonance, temperature and solvent effects.
