α-Aminophosphine-type ligands are of interest as building blocks of transition metal complexes. This review focuses on the utilization of α-aminophosphines as monodentate and bidentate ligands in platinum, palladium and rhodium complexes. Besides the linear derivatives, the applications of cyclic α-aminophosphines as ligands are also summarized. Various aspects, such as synthesis, structure and applications, as well as the catalytic activity of these complexes are discussed.
α-Aminophosphonates are of significant importance due to their biological activity. The most widely applied synthetic routes towards α-aminophosphonates are the Kabachnik-Fields reaction involving the condensation of amines, oxo compounds and >P(O)H species, such as dialkyl phosphites, and the Pudovik reaction of imines and >P(O)H reagents. By the double Kabachnik-Fields reaction, bis(aminophosphonates) have also became available. This chapter summarizes the synthesis of α-aminophosphonates and related derivatives through the two main routes as described in the literature over the last five years.
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.
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.
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