Asymmetric Transfer Hydrogenation of Prochiral Ketones Catalyzed by Ru(II)-NH-propyl-(1R,2S)-(+)-cis-1-amino-2-indanol Complexes Immobilized on SBA-15
Aneesh Mathew, Surendran Parambadath*
DOI: 10.22607/IJACS.2024.1204002
Volume 12, Issue 4 | Pages: 226-237
Abstract
NH-propyl-(1R,2S)-(+)-cis-1-amino-2-indanol (Pr-AIL) was immobilized on SBA-15 by a step by step post-synthesis
modification method. (3-chloropropyl) trimethoxysilane (3-CPTMS) was functionalized on SBA-15 further the silanol groups
were passivated by dimethoxydimethylsilane [Pr-SBA-15]. There after (1R,2S)-(+)-cis-1-amino-2-indanol (1R,2S-AIL) was
anchored over functionalized SBA-15 [PrAIL-SBA-15]. The heterogeneous catalysts were synthesized by complexation of
PrAIL-SBA-15 using [RuCl2(benzene)]2 and [RuCl2(p-cymene)]2 in 2-propanol at reflux condition and were designated as
Ru-1 and Ru-2, respectively. The synthesized heterogeneous materials were characterized by small angle X-ray diffraction
spectroscopy (SAXS), scanning electron microscopy (SEM), transmission electron microscopy (TEM), N2 adsorption-desorption
isotherms, Fourier-transform Infrared (FT-IR) spectroscopy, 29Si magic angle spinning (MAS) and 13C cross-polarization magic
angle spinning (CP-MAS) NMR spectroscopies, intensively coupled plasma atomic emission spectroscopy (ICP-AES), diffuse
reflectance UV-Vis spectroscopy, and X-ray photoelectron spectroscopy (XPS). Further, the synthesized and characterized
heterogeneous materials were successfully applied in the asymmetric transfer hydrogenation (ATH) reaction of simple prochiral
ketones. The reactions were exhibited high catalytic activities and excellent enantioselectivities for most of the simple aromatic
ketones. The factors such as time, temperature, amount of solvent, and base also were studied in detail by keeping acetophenone
as a model molecule and Ru-1 as a catalyst. In particular, these heterogeneous catalysts could be readily recovered by simple
filtration and reused in multiple consecutive catalytic runs without losing the enantiomeric excess (ee) values.
Keywords
Mesoporous molecular sieve SBA-15 Chiral amino alcohols Asymmetric transfer hydrogenation Prochiral ketones.References
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Citation
Aneesh Mathew, Surendran Parambadath*. Asymmetric Transfer Hydrogenation of Prochiral Ketones Catalyzed by Ru(II)-NH-propyl-(1R,2S)-(+)-cis-1-amino-2-indanol Complexes Immobilized on SBA-15. J Appl Pharm Sci. 2025; 12(4):226-237.