One-Pot Synthesis of α-Amino Phosphonates from Aldehydes Using Lanthanide Triflate as a Catalyst

Facile one-pot synthesis of α-amino phosphonates using lanthanide chloride as catalyst

“…The recovered catalyst was obtained from the aqueous layer after removing water. The spectral and physical data of the known compounds (4a, 4b, 4c, 4k, 4l, 4m [9], 4d, 4e, 4g, 4h, 4i, 4j [5], 4n [17]) were identical with those reported in the literature. The structure of the new compound was determined by 1 …”

“…Several Lewis acids were recently reported to be the effective catalysts for this one-pot reaction. These are rare earth triflates [5,6], indium(III) chloride [7], scandium tris(dodecyl sulfate) [8], and SmI 2 (samarium diiodide) as well [9]. Obviously, Lewis acids available in this reaction are quite few because most traditional Lewis acids such as ZnCl 2 and MgBr 2 will react with the water generated at the stage of imine formation resulting their deactivation.…”

One‐Pot Synthesis of α‐Amino Phosphonates Using Samarium Diiodide as a Catalyst Precursor

“…As many imines are unstable or difficult to purify, one-pot reactions (starting from carbonyl compounds, amines and phosphites) have also received attention. Several Lewis acids, such as rare earth triflates, [1,2] indium() chloride [3] and scandium tris(dodecyl sulfate) [4] have been found to be the most effective catalysts for this three-component reaction. However, some of them are either expensive or somewhat difficult to prepare.…”

<strong>Kabachnik&ndash;Fields synthesis of novel 2-oxoindolin methyl phosphonate derivatives using CAN.</strong>

“…Most remarkable pathway to the synthesis of α-aminophosphonates is the Kabachnik-Fields reaction, the one pot three-component reaction of aromatic/heterocyclic aldehyde, amine and triethylphosphite, also known as Kabachnik-Fields reaction [18].The novel trends in carrying out this reaction are connected with the application of (i) microwave irradiation itself or in combination with catalyst [19], (ii) ionicliquids as solvents [20],(iii) use of appropriate dehydrating agents [21]and, probably most important, (iv) the use of catalysts, was achieved by using various catalyst like ZrOCl2. 8H2O [22], YbCl3 [23], lanthanide triflates [24], Mg(ClO4)2 [25], LiClO4 [26] etc.…”

“…8H2O [22], YbCl3 [23], lanthanide triflates [24], Mg(ClO4)2 [25], LiClO4 [26] etc. Kabachnik-Fields reaction was promoted by using Cerric (IV) ammonium nitrate (CAN) as a catalyst because of its advantages like high solubility in organic solvent, ease of handling, and low toxicity [27].…”