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Issue 7, 2011
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Encapsulation of chiral Fe(salan) in nanocages with different microenvironments for asymmetric sulfide oxidation

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Abstract

The solid catalysts for asymmetric oxidation of sulfides were prepared by encapsulating a chiral iron salan complex [Fe(salan)] in the nanocages of mesoporous silicas. The microenvironment of nanocages was finely tuned using silylation reagents with different kinds of organic groups, such as propyl (C3), 1-butyl-3-propyl-4,5-dihydroimidazolium bromide (ILBr), N-propyl-N,N,N-tri-n-butylammonium chloride (TBNCl) and N-propyl-N,N,N-tri-n-butylammonium bromide (TBNBr), and investigated by water and benzene adsorption. Fe(salan) encapsulated in the amphiphilic nanocage shows much higher enantioselectivity and activity than that in hydrophobic or hydrophilic nanocage for the asymmetric oxidation of thioanisole using H2O2 as oxidant. The TOF of Fe(salan) encapsulated in the nanocage modified with TBNBr can reach as high as 220 h−1, even higher than homogeneous Fe(salan) with a TOF of 112 h−1. The enhanced catalytic activity is mainly due to the fast diffusion of H2O2 and sulfide in the amphiphilic nanocage. The above results suggest that the microenvironment modification of the nanocage is an efficient method to synthesize highly efficient solid catalysts for asymmetric catalysis.

Graphical abstract: Encapsulation of chiral Fe(salan) in nanocages with different microenvironments for asymmetric sulfide oxidation

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Publication details

The article was received on 15 Sep 2010, accepted on 21 Oct 2010 and first published on 09 Dec 2010


Article type: Paper
DOI: 10.1039/C0CP01828G
Citation: Phys. Chem. Chem. Phys., 2011,13, 2504-2511
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    Encapsulation of chiral Fe(salan) in nanocages with different microenvironments for asymmetric sulfide oxidation

    B. Li, S. Bai, P. Wang, H. Yang, Q. Yang and C. Li, Phys. Chem. Chem. Phys., 2011, 13, 2504
    DOI: 10.1039/C0CP01828G

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