Abstract
An effective technique was proposed for the synthesis of novel α-aminophosphonates: a three-component one-pot condensation reaction of aniline, aromatic aldehydes, and triphenyl phosphite in the presence of (MIL-100(Fe)) as a heterogeneous catalyst. Initially, MIL-100(Fe) was synthesized using H3BTC and ferric nitrate at low temperature and atmospheric pressure. Further, MIL-100(Fe) was characterized using various techniques such as XRD, BET surface area, scanning electron microscopy (SEM), Fourier-transform infrared (FT-IR), and thermogravimetric analysis (TGA). Herein, MIL-100(Fe) showed exceptional catalytic performance for the synthesis of α-aminophosphonate and its derivatives compared with conventional solid catalysts, and even homogeneous catalysts. The study demonstrated that MIL-100(Fe) is an ecofriendly and easily recyclable heterogeneous catalyst in Kabachnick reactions for α-aminophosphonate synthesis, with high yield (98%) and turnover frequency (TOF ~ 3.60 min−1) at room temperature and a short reaction time (30 min).
Highlights
IntroductionOrganophosphorus compounds, especially α-aminophosphonic acids (I) and their esters (II), possess the capacity for biological action because of their resemblance to α-amino acids (III)
Organophosphorus compounds, especially α-aminophosphonic acids (I) and their esters (II), possess the capacity for biological action because of their resemblance to α-amino acids (III). They are an important analog to α-amino acids (III); as such, we substituted a carboxylic group with a phosphonic acid ester moiety (Scheme 1) [1]
Catalyst ing at 8 wt% was decided as the optimal condition for further series studies; according to loading at 8 wt% was decided as the optimal condition for further series studies; according the experimentaltoresults, we suggest possible reaction in in the experimental results,one we suggest onemechanism possible mechanism reaction
Summary
Organophosphorus compounds, especially α-aminophosphonic acids (I) and their esters (II), possess the capacity for biological action because of their resemblance to α-amino acids (III). Due to the amazing pharmacological and environmental applications of α-aminophosphonic acids and their related derivatives, α-aminophosphonate, and its analogs have recently attracted the attention of the scientific community [2,3] These organophosphorus compounds have high biological efficiency, metabolic stability, and low toxicity in mammalian cells [2]. The inhomogeneous blending of the components is one of the most challenging downsides of MOF-based composites, since the finished composite does not have a regular distribution throughout the product or demonstrate any well-enhanced performance in applications One solution to this problem is to use well-shaped nanoparticles as hard templates that lead the material component of the composite through a regulated bottom-up growth process, which assures uniformity. MIL-100(Fe) was utilized as a recyclable catalyst in Kabachnick reactions for α-aminophosphonate synthesis, with high yields in mild conditions. To the best of our knowledge, hardly any study has been conducted on the synthesis of α-aminophosphonates catalyzed by MOFs
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