Immobilization of chiral oxazaborolidine catalyst over highly ordered 3D mesoporous silica with Ia3d symmetry for enantioselective reduction of prochiral ketone

Velmathi, Sivan, Balakrishnan, Umesh, Ananthi, Nallamuthu, Aldeyab, Salem S., Ariga, Katsuhiko, Naidu, Talapaneni Siddulu and Vinu, Ajayan (2011) Immobilization of chiral oxazaborolidine catalyst over highly ordered 3D mesoporous silica with Ia3d symmetry for enantioselective reduction of prochiral ketone. Physical Chemistry Chemical Physics, 13 11: 4950-4956. doi:10.1039/c0cp02067b


Author Velmathi, Sivan
Balakrishnan, Umesh
Ananthi, Nallamuthu
Aldeyab, Salem S.
Ariga, Katsuhiko
Naidu, Talapaneni Siddulu
Vinu, Ajayan
Title Immobilization of chiral oxazaborolidine catalyst over highly ordered 3D mesoporous silica with Ia3d symmetry for enantioselective reduction of prochiral ketone
Formatted title
Immobilization of chiral oxazaborolidine catalyst over highly ordered 3D mesoporous silica with Ia3d symmetry for enantioselective reduction of prochiral ketone
Journal name Physical Chemistry Chemical Physics   Check publisher's open access policy
ISSN 1463-9076
1463-9084
Publication date 2011-01-01
Sub-type Article (original research)
DOI 10.1039/c0cp02067b
Open Access Status Not Open Access
Volume 13
Issue 11
Start page 4950
End page 4956
Total pages 7
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Language eng
Formatted abstract
Here we demonstrate for the first time the encapsulation of a chiral oxazaborolidine complex in the 3D mesoporous channels of an amine functionalized KIT-6 material via covalent bonding through a post-synthetic approach. The physico-chemical properties of the pure and immobilized KIT-6 catalysts were obtained by various techniques such as XRD, nitrogen adsorption, HRSEM, UV-Vis diffuse reflectance spectroscopy, and FT-IR spectroscopy. It has been found that the structural stability of the KIT-6 was not affected even after the immobilization of a significant amount of chiral ligand inside the mesoporous channels of the support. However, the values of structural parameters such as the specific surface area and the specific pore volume of the KIT-6 support was significantly lower than the pure KIT-6 support. The chemical interaction between the chiral ligand inside the mesochannels and the KIT-6 support was also confirmed by UV-Vis and FT-IR spectroscopy. The chiral catalytic performance of the immobilized catalysts for the enantioselective reduction of aromatic prochiral ketones was demonstrated and the results were compared with chiral catalyst immobilized supports with uni-dimensional porous structures, such as MCM-41 and SBA-15. Among the catalysts studied, chiral catalyst immobilized KIT-6 showed the highest performance with a high product yield and a high enantioselectivity due to its 3D porous structure with two continuous and interpenetrating systems of chiral channels and an interwoven 3D cylindrical type pores of Ia3d symmetry. The catalyst also exhibited much better recycling capability than other chiral catalyst supported mesoporous materials used in the study.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: Australian Institute for Bioengineering and Nanotechnology Publications
 
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