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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. |
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Key words: Mesoporous molecular sieve, SBA-15,
Chiral amino alcohols, Asymmetric transfer hydrogenation, Prochiral
ketones. |
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Indian Journal of Advances in Chemical Science,
Volume: 12, Issue : 4, December 2024
ISSN No.: 2320-0898 (Print);
2320-0928 (Electronic) |
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