Ultrafast synthesis of α-aminophosphonates using ternary deep eutectic solvent in water
A remarkably rapid synthesis of α-aminophosphonate medicinally privileged scaffold is developed using a ternary deep eutectic solvent (TDES) of urea/SnCl<sub>2</sub>/HCl catalyst. Newly promoted TDES enabled a sustainable pathway to a library of the desired compounds with divergent electronic and steric characteristics simply using water as the solvent. The TDES-promoted protocol boasts unusual reaction times of 48-120 s, particularly for a batch chemistry process of organic synthesis, selectively churning out quantitative yields of a range of α-aminophosphonates. The catalyst entails total atom economy in its synthesis, and with a kinematic viscosity of 2.68 mm<sup>2</sup>.s<sup>-1</sup>, it is freely flowing at room temperature, making it a worthwhile candidate for utilization in large-scale process chemistry. The protocol is amenable to scaled-up synthesis as the use of the stable catalyst enabled its retrieval and reuse in at least three successive runs. <sup>119</sup>Sn-NMR and<sup>13</sup>C-NMR spectroscopy techniques were employed to fully characterize the TDES catalyst produced from cheap, abundant chemicals. Additionally, UV-VIS analysis was adopted for monitoring the extraordinarily swift synthetic procedure, and stereochemical assignment analysis was implemented for α-aminophosphonate products using NMR spectroscopy, highlighting the synthetic selectivity of the process.
Authors
- Navid Habibnejad (ORCID: https://orcid.org/0000-0003-2730-439X)
- Narges Azizi (ORCID: https://orcid.org/0000-0003-2464-2473)
- Mehran Shahiri Haghayegh
- Nasim Nourazar
Institutions
- Chemistry and Chemical Engineering Research Center of Iran (IR)
Publication Details
- Journal
- Scientific Reports
- Published
- 2025-12-21
- DOI
- https://doi.org/10.1038/s41598-025-31806-4
- Primary Topic
- Organophosphorus compounds synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00