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Issue 42, 2009
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Chirally functionalized mesoporous organosilicas with built-in BINAP ligand for asymmetric catalysis

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Abstract

The chirally functionalized periodic mesoporous organosilica (PMO) with C2-symmetric chiral building blocks, BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl), in the pore wall was successfully synthesized for the first time using a successive co-condensation and post-synthesis modification method. Chiral BINAPO (2,2′-bis(diphenylphosphinooxide)-1,1′-binaphthyl) bridging mesoporous organosilica with highly ordered 2-D hexagonal structure was first synthesized by co-condensation of (R)-5,5′-bis(3-triethoxysilylpropyl-1-ureyl)-2,2′-bis(diphenylphosphinooxide)-1,1′-binaphthy with tetramethoxylsilane in the presence of block copolymer P123 as template under weakly acidic conditions. The BINAPO in the pore wall of PMO was reduced with trichlorosilane to generate BINAP using a post-synthesis modification method. The chiral PMO with built-in BINAP (coordination with [RuCl2-(benzene)]2) is an efficient solid catalyst for the asymmetric hydrogenation of β-keto esters with ee as high as 99%, which is among the highest ever reported for the chirally functionalized PMOs in asymmetric catalysis.

Graphical abstract: Chirally functionalized mesoporous organosilicas with built-in BINAP ligand for asymmetric catalysis

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Publication details

The article was received on 10 Jul 2009, accepted on 25 Aug 2009 and first published on 21 Sep 2009


Article type: Paper
DOI: 10.1039/B913808K
Citation: J. Mater. Chem., 2009,19, 8009-8014
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    Chirally functionalized mesoporous organosilicas with built-in BINAP ligand for asymmetric catalysis

    P. Wang, X. Liu, J. Yang, Y. Yang, L. Zhang, Q. Yang and C. Li, J. Mater. Chem., 2009, 19, 8009
    DOI: 10.1039/B913808K

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