Reusable Pd-polyHIPE for Suzuki–Miyaura coupling

Ravbar, Miha (author), Koler, Amadeja (author), Paljevac, Muzafera (author), Krajnc, Peter (author), Kolar, Mitja (author), Iskra, Jernej (author)

Palladium was immobilized on a highly porous copolymer of 4-vinylpyridine and divinylbenzene (polyHIPE─poly(high internal phase emulsion)) using palladium(II) acetate to obtain PolyPy-Pd with 6.1 wt % or 0.57 mmol Pd/g. The immobilized catalyst was able to catalyze the coupling of iodobenzene and phenylboronic acid in ethylene glycol monomethyl ether/water (3:1) within 4 h at rt and complete conversion was observed when 2.5 mol % of Pd per PhI was used. The reaction tolerated a wide range of substituents on the aromatic ring. Iodobenzene derivatives with electron-withdrawing substituents showed higher reactivity, while the opposite was true for the phenylboronic acid series. The polyHIPE-supported Pd catalyst was also used for the direct conversion of phenylboronic acid to biphenyl through an iodination/coupling reaction sequence. The recyclability of the heterogeneous catalyst was also optimized, and by finding a suitable combination of solvents for the loading of Pd, the reaction, and the isolation of the product, the solid-supported catalyst was completely regenerated and used in the next reaction with the same activity.

• Language: English
• Keywords: palladium, mixtures, catalysts, solvents, polymers
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2022
• Number of pages: Str. 12610-12616
• Numbering: Vol. 7, iss. 15
• PID: 20.500.12556/RUL-136962
• UDC: 66.02
• ISSN on article: 2470-1343
• DOI: 10.1021/acsomega.1c06318
• COBISS.SI-ID: 104201731
• Publication date in RUL: 26.05.2022

Record is a part of a journal

• Title: ACS omega
• Shortened title: ACS omega
• Publisher: American Chemical Society
• ISSN: 2470-1343
• COBISS.SI-ID: 525873945

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.

Secondary language

• Language: Slovenian
• Keywords: paladij, mešanice, kataliza, polimeri