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Issue 29, 2018
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Silica-supported silver nanoparticles as an efficient catalyst for aromatic C–H alkylation and fluoroalkylation

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Abstract

The efficient catalysis of oxidative alkylation and fluoroalkylation of aromatic C–H bonds is of paramount importance in the pharmaceutical and agrochemical industries, and requires the development of convenient Ag0-based nano-architectures with high catalytic activity and recyclability. We prepared Ag-doped silica nanoparticles (Ag0/+@SiO2) with a specific nano-architecture, where ultra-small sized silver cores are immersed in silica spheres, 40 nm in size. The nano-architecture provides an efficient electrochemical oxidation of Ag+@SiO2 without any external oxidant. In turn, Ag+@SiO2 5 mol% results in 100% conversion of arenes into their alkylated and fluoroalkylated derivatives in a single step at room temperature under nanoheterogeneous electrochemical conditions. Negligible oxidative leaching of silver from Ag0/+@SiO2 is recorded during the catalytic coupling of arenes with acetic, difluoroacetic and trifluoroacetic acids, which enables the good recyclability of the catalytic function of the Ag0/+@SiO2 nanostructure. The catalyst can be easily separated from the reaction mixture and reused a minimum of five times upon electrochemical regeneration. The use of the developed Ag0@SiO2 nano-architecture as a heterogeneous catalyst facilitates aromatic C–H bond substitution by alkyl and fluoroalkyl groups, which are privileged structural motifs in pharmaceuticals and agrochemicals.

Graphical abstract: Silica-supported silver nanoparticles as an efficient catalyst for aromatic C–H alkylation and fluoroalkylation

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Publication details

The article was received on 21 Mar 2018, accepted on 15 May 2018 and first published on 16 May 2018


Article type: Paper
DOI: 10.1039/C8DT01090K
Citation: Dalton Trans., 2018,47, 9608-9616
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    Silica-supported silver nanoparticles as an efficient catalyst for aromatic C–H alkylation and fluoroalkylation

    M. N. Khrizanforov, S. V. Fedorenko, A. R. Mustafina, K. V. Kholin, I. R. Nizameev, S. O. Strekalova, V. V. Grinenko, T. V. Gryaznova, R. R. Zairov, R. Mazzaro, V. Morandi, A. Vomiero and Y. H. Budnikova, Dalton Trans., 2018, 47, 9608
    DOI: 10.1039/C8DT01090K

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