This perspective summarizes the utilization of α-aminophosphines as monodentate and bidentate ligands in the synthesis of platinum, palladium and rhodium complexes.
Novel 1,2,3-triazol-5-yl-phosphonates were prepared by the copper(I)-catalyzed domino reaction of phenylacetylene, organic azides and dialkyl phosphites. The process was optimized on the synthesis of the dibutyl (1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)phosphonate in respect of the catalyst, the base and the solvent, as well as of the reaction parameters (molar ratio of the starting materials, atmosphere, temperature and reaction time). The method elaborated could be applied to a range of organic azides and dialkyl phosphites, which confirmed the large scope and the functional group tolerance. The in vitro cytotoxicity on different cell lines and the antibacterial activity of the synthesized 1,2,3-triazol-5-yl-phosphonates was explored. According to the IC50 values determined, only modest antibacterial effect was detected, while some derivatives showed moderate activity against human promyelocytic leukemia HL-60 cells.
15 February 2019 in Beilstein Journal of Organic Chemistry
A family of N,N-bis(phosphinoylmethyl)amines bearing different substituents on the phosphorus atoms was synthesized by the microwave-assisted and catalyst-free Kabachnik–Fields reaction of (aminomethyl)phosphine oxides with paraformaldehyde and diphenylphosphine oxide. The three-component condensation of N,N-bis(phosphinoylmethyl)amine, paraformaldehyde and a secondary phosphine oxide affording N,N,N-tris(phosphinoylmethyl)amine derivatives was also elaborated. This method is a novel approach for the synthesis of the target products.
A series of acylated α-aminophosphine oxides were synthesized by the microwave-assisted Kabachnik–Fields reaction of a series of carboxylic acid amides, formaldehyde and secondary phosphine oxides. To compensate the lower reactivity of the –NH2 reagents, they had to be used in an excess. The solvolytic condensations furnished the α-aminophosphine oxides in yields of 58–93% after purification by chromatography.
An efficient and practical method was developed for the synthesis of new (1,2,3‑triazol‑4‑yl)methyl phosphinates and (1,2,3-triazol-4-yl)methyl phosphates by the copper(I)‑catalyzed azide-alkyne cycloaddition (CuAAC) of organic azides and prop-2-ynyl phosphinate or prop-2-ynyl phosphate. The synthesis of (1‑benzyl-1H-1,2,3-triazol-4-yl)methyl diphenylphosphinate was optimized with respect to the reaction parameters, such as the temperature, reaction time, and catalyst loading. The approach was applied to a range of organic azides, which confirmed the wide scope and the substituent tolerance of the process. The method elaborated represents a novel approach for the synthesis of the target compounds.
22 February 2019 in Phosphorus, Sulfur, and Silicon and the Related Elements
Aminophosphine oxides and bis(phosphinoylmethyl)amines were synthesized by the microwave (MW)-assisted Kabachnik-Fields reaction of primary amines, paraformaldehyde and secondary phosphine oxides. The bisphosphines obtained after deoxygenation of the bis(phosphinoymethyl)amine derivatives were utilized in the synthesis of cyclic transition metal complexes.