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Silica-supported silver nanoparticles as an efficient catalyst for aromatic C-H alkylation and fluoroalkylation
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, Russian Federation.
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, Russian Federation.
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, Russian Federation.
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, Russian Federation.
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2018 (English)In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 47, no 29, p. 9608-9616Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2018. Vol. 47, no 29, p. 9608-9616
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Experimental Physics
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URN: urn:nbn:se:ltu:diva-69113DOI: 10.1039/c8dt01090kPubMedID: 29855006Scopus ID: 2-s2.0-85050861647OAI: oai:DiVA.org:ltu-69113DiVA, id: diva2:1213580
Note

Validerad;2018;Nivå 2;2018-08-08 (andbra)

Available from: 2018-06-05 Created: 2018-06-05 Last updated: 2018-08-13Bibliographically approved

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Mazzaro, RaffaelloVomiero, Alberto

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