Issue 97, 2015

Insight into the catalytic properties and applications of metal–organic frameworks in the cyanosilylation of aldehydes

Abstract

Here we present a systematic investigation of the cyanosilylation of aldehydes with trimethylsilyl cyanide (TMSCN) by using metal–organic frameworks (MOFs) as catalysts. Four types of thermally stable MOFs (MIL-47 (V), MIL-53 (Al), MIL-101 (Cr), and UiO-66 (Zr)) constructed with the same organic linker, terephthalic acid, were studied, among which MIL-101 (Cr) exhibits the highest catalytic activity. Experimental results revealed that the catalytic activities are in close relation with the types of coordinatively unsaturated metal ions, pore sizes as well as solvents. Using MIL-101 (Cr) as the catalyst, both aliphatic and aromatic aldehydes were efficiently transformed to cyanohydrin trimethylsilyl ether, meanwhile significant size selectivities and electronic effects have also been observed. The solvent-free reaction conditions not only provide a high TON for MOF catalyzed cyanosilylation, but also render the current protocol more attractive to industrial applications.

Graphical abstract: Insight into the catalytic properties and applications of metal–organic frameworks in the cyanosilylation of aldehydes

Supplementary files

Article information

Article type
Paper
Submitted
05 Jul 2015
Accepted
27 Aug 2015
First published
27 Aug 2015

RSC Adv., 2015,5, 79355-79360

Author version available

Insight into the catalytic properties and applications of metal–organic frameworks in the cyanosilylation of aldehydes

Z. Zhang, J. Chen, Z. Bao, G. Chang, H. Xing and Q. Ren, RSC Adv., 2015, 5, 79355 DOI: 10.1039/C5RA13102B

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