59374-38-8

Upstream product

• 762-04-9 Diethyl phosphonate 
• 123-11-5 4-methoxy-benzaldehyde 
• 104-94-9 4-methoxy-aniline 
• 122-52-1 triethyl phosphite 
• 762-04-9 phosphonic acid diethyl ester 
• 1749-08-2 N-(4-methoxy benzylidene)-4-methoxyaniline 
• 78-40-0 triethyl phosphate 

Downstream Products

• 1123496-75-2 C₃₆H₃₀NO₅P 

Relevant academic research and scientific papers

ZnO nanoparticles as an efficient catalyst for the one-pot synthesis of α-amino phosphonates

Zinc oxide nanoparticles (ZnO NPs, ca. 22 nm) were used as an effective catalyst in the solvent-free, three-component couplings of aldehydes, aromatic amines and dialkyl phosphites at room temperature to produce various α-amino phosphonates. Compared to known methods, satisfactory results were obtained with high yields through a simple experimental procedure. The catalyst was recycled and reused five times with minor decrease in its catalytic activity. Georg Thieme Verlag Stuttgart.

Synthesis and structural characterization of homochiral 2D coordination polymers of zinc and copper with conformationally flexible ditopic imidazolium-based dicarboxylate ligands

Different novel coordination polymers containing zinc, 1-4, and copper, 5-8, metals, connected via chiral imidazolium-based dicarboxylate ligands, [LR]?, were isolated by reaction between zinc acetate or copper acetate and enantiomerically pure HLR compounds. They were characterised and structurally identified by X-ray diffraction methods (single crystal and powder). These compounds are two-dimensional homochiral coordination polymers, [M(LR)2]n, in which the metal ions are coordinated by the two carboxylate groups of [LR]? anions in a general bridging monodentate μ2-κ1-O1,κ1-O3 fashion that afforded tetrahedral metal coordination environments for zinc, 1-4, and square planar for copper, 5-8, complexes. In all the compounds the 3D supramolecular architecture is constructed by non-covalent interactions between the hydrophobic parts (R groups) of the homochiral 2D coordination polymers and, in some cases, by weak C-H?O non-classical hydrogen bonds that provided, in general, a dense crystal packing. DFT calculations on the [LR]? anions confirmed their conformational flexibility as ditopic linkers and this fact makes possible the formation of different coordination polymers for four-coordinated metal centers. Preliminary studies on the Zn-catalyzed synthesis of chiral α-aminophosphonates were carried out and, unfortunately, no enantioselectivity was observed in these reactions.

Synthesis and structural characterization of homochiral coordination polymers with imidazole-based monocarboxylate ligands

Chiral Na[(S)-LR] (R = Me, 1a; iPr, 1b; CH2iPr, 1c, and (S)-secBu, 1d) and Na[(R)-LR] (R = Me, 1a′) compounds were synthesised following standard procedures. New compounds 1d and 1a′ were analytically and spectroscopically characterised. 1a and 1c were structurally identified by single-crystal X-ray diffraction methods as homochiral 2D coordination polymers, {Na(H2O)[(S)-LMe]}n and {Na[(S)-L CH2iPr]}n, respectively. Both (S)-2alkyl,2-(1H-imidazol-1-yl)acetate anions displayed unprecedented coordination modes in these coordination polymers: μ3κ2OκO′ for 1a and μ4κ2Oκ2O′ for 1c. Enantiomeric species 1a′, {Na(H2O)[(R)-LMe]}n, showed the same X-ray powder diffractogram (XRPD) as 1a, in agreement with a similar crystal structure. DFT calculations on the [LR]- anions confirmed their coordination capabilities as ditopic linkers. In fact, the reaction of Na[LR] with several metal salts yielded the following coordination polymers: {Ag[(S)-LMe]}n, 2a, {Ag[(R)-LMe]}n, 2a′, {Cu[(S)-LR]2}n (R = Me, 3a; iPr, 3b), {Cu[(R)-LMe]}n, 3a′, {Zn[(S)-LR]2}n (R = Me, 4a; iPr, 4b; (S)-secBu, 4d) and {Zn[(R)-LMe]2}n, 4a′. For the known compounds 3a and 4a, this procedure is a new synthetic route that avoided high temperature reaction conditions. New complexes 2, 3a′, b, and 4a′, b, d were characterised by elemental analysis, infrared and XRPD methods and complex 2a by single-crystal X-ray diffraction. This complex is also a two-dimensional coordination polymer in which the [(S)-LMe]- anion acts as a μ4κN,κ2O,κ2O′ bridging ligand. Compounds 1-4a′ are the first examples of homochiral coordination polymers with imidazole-monocarboxylate ligands based on non-natural amino acids. Preliminary studies on the metal-catalysed preparation of chiral α-aminophosphonates were carried out but, unfortunately, no enantioselectivity was observed.

Niobium pentoxide, a recyclable heterogeneous solid surface catalyst for the synthesis of α-amino phosphonates

Abstract: Niobium pentoxide, a bifunctional solid surface catalyst, has been successfully employed to facilitate the three-component reaction between aldehydes, amines and triethyl phosphite at room temperature under solvent-free conditions to generate α-amino phosphonate in moderate to good yields. The catalyst can be recycled through simple filtration and reused to effect this transformation. Graphic abstract: [Figure not available: see fulltext.].

Magnetic ZnO?CuO?Iron ore nanocomposites as a green and highly efficient heterogeneous nanocatalyst for solventless synthesis of α-aminophosphonates

A green novel synthesis of ZnO?CuO?Iron ore nanocomposites as a novel and magnetic heterogeneous nanocatalyst is used for the one-pot synthesis of α-aminophosphonates under solventless conditions. This study benefits from the magnetic iron ore acting as a multi-mineral Lewis acid system, the green properties and the large surface area due to its nanostructure. Moreover, scanning electron microscope analysis confirmed that the nanocatalyst gave an excellent yield and good recyclability; which, even after the 10th cycle of the model reaction retained its potential with no significant loss of catalytic activity.

Catalyst free one-pot synthesis of α-aminophosphonates in aqueous ethyl lactate

An highly efficient and environmentally friendly process for the synthesis of α-aminophosphonates has been devised, through a one-pot three-component condensation of various aldehydes, amines and triethyl phosphate in water-ethyl lactate under ultrasonic

A green one-pot three-component synthesis of α-aminophosphonates under solvent-free conditions and ultrasonic irradiation using Fe3O4@SiO2-imid-PMAn as magnetic catalyst

An efficient and environment friendly process for the synthesis of α-aminophosphonates has been devised. Through a one-pot three-component condensation of various aldehydes, amines, and triethyl phosphite in the presence of Fe3O4@SiO2-imid-PMAn nanoparticles as magnetic catalysts under solvent-free conditions and ultrasonic irradiation, α-aminophosphonates were obtained with excellent yields. The reactions under solvent-free conditions at room temperature are compared with the ultrasonic-assisted reactions. This new procedure has notable advantages such as short reaction time, excellent yields, easy purification, and the absence of any tedious workup or purification. The aforementioned catalyst could be easily recovered by an external magnetic field and can be reused for six consecutive reaction cycles without significant loss of activity. In addition, SEM and DLS of the catalyst after the reaction cycle were investigated.

Iron-doped single walled carbon nanotubes as an efficient and reusable heterogeneous catalyst for the synthesis of organophosphorus compounds under solvent-free conditions

Iron-doped single walled carbon nanotubes (Fe/SWCNTs) is an efficient, eco-friendly, and reusable heterogeneous catalyst for the synthesis of diversely decorated α-aminophosphonates via multicomponent reaction of amines, carbonyl compounds, and phosphorus compounds under solvent-free conditions. This methodology illustrates a very simple procedure, with wide applicability, extending the scope to aliphatic and aromatic amines and carbonyl compounds. It also enabled the development of one-pot synthesis of β-phosphonomalonates during the reaction of carbonyl compounds, malononitrile and phosphorus compounds. Excellent results were obtained in each case affording the corresponding organophosphorus adducts in good yields.

Gold complex-catalyzed CP bond formation by Kabachnik-Fields reactions

CP bond formation was realized through the three-component reaction of an amine, an aldehyde and a dialkylphosphite catalyzed by gold complex. The corresponding α-aminophosphonates were afforded in one-pot reaction with high yields under mild conditions.

Lanthanide amido complexes incorporating amino-coordinate-lithium bridged bis(indolyl) ligands: Synthesis, characterization, and catalysis for hydrophosphonylation of aldehydes and aldimines

Two series of new lanthanide amido complexes supported by bis(indolyl) ligands with amino-coordinate-lithium as a bridge were synthesized and characterized. The interactions of [(Me3Si)2N] 3LnIII(μ-Cl)Li(THF)su