Journal
GREEN CHEMISTRY
Volume 15, Issue 8, Pages 2208-2214Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3gc40547h
Keywords
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Funding
- China National Natural Science Foundation [20673072]
- Shanghai Sciences and Technologies Development Fund [10DJ1400103, 10JC1412300, 12nm500500]
- CSIRT [IRT1269]
- Shanghai Municipal Education Commission [12ZZ135]
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Functionalized flower-like mesoporous silica with a chiral organorhodium functionality incorporated within its silica framework is prepared through an assembly of chiral 4-((trimethoxysilyl)ethyl) phenylsulfonyl-1,2-diphenylethylenediamine and tetraethoxysilane under a cooperative dual-template approach followed by complexation with organorhodium complexes. Structural characterization discloses its mesostructure and well-defined single-site chiral organorhodium functionality, while electron microscopy analyses reveal the uniformly distributed three-dimensional spherical flowers constructed by the stacking of leaf-shaped nanoflakes. In particular, as a bifunctionalized heterogeneous catalyst, it shows excellent catalytic activity and high enantioselectivity in the asymmetric transfer hydrogenation of aromatic ketones in aqueous medium (more than 99% conversion and up to 97% ee). The superior catalytic performance is attributed to the synergistic effect of the salient cetyltrimethylammonium bromide phase-transfer function and confined chiral organorhodium catalytic nature. Furthermore, this heterogeneous catalyst could be recovered easily and reused repeatedly (ten times) without affecting its ee value, showing a practical application in asymmetric synthesis.
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