Chiral Modification of Ferrite Nanoparticles for Oxidative Kinetic Resolution of Benzoins

• Published in: Asian journal of organic chemistry 2023-08, Vol.12 (8), p.n/a
• Main Authors: Gupta, Pranshu K., Kumar, Neeraj, Majumder, Abir B., Pandey, Manisha, Goverdhan R. P, Vasu, Ranganath, Kalluri V. S.
• Format: Article
• Language: English
• Subjects: Benzoin; Chiral materials; Copper; Ferrites; Heterogeneous; Iron oxides; Manganese; Nanoparticles; Organic chemistry; Photoelectrons; Recyclability; Surface Modification; Surfactants; Synthesis; Thermogravimetric analysis; X ray photoelectron spectroscopy
• ISSN: 2193-5807; 2193-5815
• DOI: 10.1002/ajoc.202300325

We report the surface modification of ferrite nanoparticles (MFe2O4 NPs; M= Mn, Fe, Co, Ni, Cu, Zn) with chiral surfactants derived from cinchona alkaloids. The successful synthesis of chiral ferrites were characterized using powder X‐ray diffraction (PXRD), X‐ray photoelectron spectroscopy (XPS), Atomic force microscopy (AFM), Thermogravimetric analysis (TGA) and vibrating sample magnetometer (VSM). These chiral materials were highly active in the oxidative kinetic resolution (OKR) of racemic benzoins. Remarkably gemini surfactant modified Fe3O4 NPs were found to be a potential candidate in the OKR and (R)‐benzoin was isolated with 97% enantiomeric excess (ee). The sustainability of our catalyst has been demonstrated in the gram scale synthesis of (R)‐furoin (93% ee). The recyclability studies have also been performed and found that it could be recyclable with decrease in ee. We report the synthesis of chiral gemini surfactant modified magnetite nanoparticles. These chiral NPs are characterized by PXRD, XPS, Zeta Potential, DLS, TGA and VSM. Thus well characterized chiral NPs are proved to be a potential candidates in the OKR of various racemic benzoins and provided ee up to 97% with selectivity s=12.0. The applicability of our chiral ferrites has also been demonstrated in the gram scale kinetic resolution of racemic furoin.