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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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Supplementary files

Article information


Submitted
21 Marts 2018
Accepted
15 Maijs 2018
First published
16 Maijs 2018

Dalton Trans., 2018,47, 9608-9616
Article type
Paper

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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