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Full factorial optimization of α-aminophosphonates synthesis using diphenylphosphinic acid as efficient organocatalyst

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Abstract

Diphenylphosphinic acid was used as an efficient and simple catalyst for the synthesis of the α-aminophosphonates by multicomponent Kabachnik-Fields reaction in one pot of aromatic aldehyde, aniline and diethylphosphite. Three physicochemical factors including catalyst amount, reaction time and medium temperature were optimized using a full factorial experiment design (FFD). Additionally, a quadratic polynomial regression model was applied for the analysis of the experimental data at a confidence level of 95% with p-values < 0.05. The high signification effect of the reaction time and the medium temperature on the α-aminophosphonates synthesis were confirmed by the statistical analysis. Besides, the diphenylphosphinic acid amount showed an effect on the reaction yield. ANOVA exhibited that the coefficient determination of this model up to 99.25%. This eco-friendly procedure was extended for the preparation of series of the α-aminophosphonates in ethanol as green solvent, giving the desired products with high chemical yields up to 90%.

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Scheme 1

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In good to excellent chemical yields (from 78% to 98%).

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Acknowledgements

The General Directorate of Scientific Research and Technological Development (DGRSDT) is gratefully acknowledged for financial support of this work. The technical support provided by Emilie KOLODZIEJ is highly appreciated.

Funding

This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.

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Authors and Affiliations

  1. Ecocompatible Asymmetric Catalysis Laboratory (LCAE), Badji Mokhtar Annaba-University, B.P 12, 23000, Annaba, Algeria

    Meriem Ferrah, Samia Guezane-Lakoud, Rym Aissa, Mounia Merabet-Khelassi & Louisa Aribi-Zouioueche

  2. Laboratory of Physical Chemistry and Biology of Materials, Higher Normal School of Technological Education (ENSET), 21000, Skikda, Algeria

    Hacene Bendjeffal

  3. Equipe de Catalyse Moléculaire-ICMMO Bât 420, Université Paris-Saclay, Saclay, France

    Martial Toffano

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  1. Meriem Ferrah
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Contributions

All authors contributed to this manuscript. MF: Synthesis of molecules. SGL: wrote, conceived and designed the study and Methodology, HB: Wrote and designed the full factorial experiment. RA: Investigation. MMK: wrote and investigated. MT: performed the data analysis and wrote this manuscript. LAZ: Wrote and revised.

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Correspondence to Samia Guezane-Lakoud.

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Ferrah, M., Guezane-Lakoud, S., Bendjeffal, H. et al. Full factorial optimization of α-aminophosphonates synthesis using diphenylphosphinic acid as efficient organocatalyst. Reac Kinet Mech Cat 136, 165–182 (2023). https://doi.org/10.1007/s11144-022-02329-0

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