Acrylamide-based Pd-Nanoparticle Carriers as Smart Catalyst for the Suzuki-Miyaura Cross-Coupling of Amino Acids

Sabadasch V, Dachwitz S, Hannappel Y, Hellweg T, Sewald N (2022)
Synthesis.

Zeitschriftenaufsatz | E-Veröff. vor dem Druck | Englisch
 
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Abstract / Bemerkung
Polyacrylamide-based waterborne microgels were prepared with copolymerized carboxylic acid and tertiary amine moieties. The colloidal gels were loaded with palladium nanoparticles and utilized for the Suzuki-Miyaura cross-coupling of amino acids and peptides. The thermoresponsive properties of the prepared microgels were characterized by means of photon correlation spectroscopy (PCS) at solvent conditions of the catalytic reaction. The localization and morphology of the incorporated nanoparticles were characterized with transmission electron microscopy (TEM). Palladium-catalyzed Suzuki-Miyaura cross-coupling of Nα-Boc-4 iodophenylalanine and Nα-Boc-7-bromotryptophan with phenylboronic acid was carried out under ambient atmosphere in water at 20 °C, 37 °C and 60 °C, respectively. The properties of the thermoresponsive microgel showed a strong influence on the reactivity and selectivity towards the respective substrate. For the amine containing microgels a recyclability for up to four cycles without loss in activity could be realized. Furthermore, the systems showed good catalytic activity regarding Suzuki-Miyaura cross-coupling of halogenated amino acids in selected tri- and tetrapeptides.
Erscheinungsjahr
2022
Zeitschriftentitel
Synthesis
ISSN
0039-7881
eISSN
1437-210X
Page URI
https://pub.uni-bielefeld.de/record/2961430

Zitieren

Sabadasch V, Dachwitz S, Hannappel Y, Hellweg T, Sewald N. Acrylamide-based Pd-Nanoparticle Carriers as Smart Catalyst for the Suzuki-Miyaura Cross-Coupling of Amino Acids. Synthesis. 2022.
Sabadasch, V., Dachwitz, S., Hannappel, Y., Hellweg, T., & Sewald, N. (2022). Acrylamide-based Pd-Nanoparticle Carriers as Smart Catalyst for the Suzuki-Miyaura Cross-Coupling of Amino Acids. Synthesis. https://doi.org/10.1055/a-1782-4224
Sabadasch, Viktor, Dachwitz, Steffen, Hannappel, Yvonne, Hellweg, Thomas, and Sewald, Norbert. 2022. “Acrylamide-based Pd-Nanoparticle Carriers as Smart Catalyst for the Suzuki-Miyaura Cross-Coupling of Amino Acids”. Synthesis.
Sabadasch, V., Dachwitz, S., Hannappel, Y., Hellweg, T., and Sewald, N. (2022). Acrylamide-based Pd-Nanoparticle Carriers as Smart Catalyst for the Suzuki-Miyaura Cross-Coupling of Amino Acids. Synthesis.
Sabadasch, V., et al., 2022. Acrylamide-based Pd-Nanoparticle Carriers as Smart Catalyst for the Suzuki-Miyaura Cross-Coupling of Amino Acids. Synthesis.
V. Sabadasch, et al., “Acrylamide-based Pd-Nanoparticle Carriers as Smart Catalyst for the Suzuki-Miyaura Cross-Coupling of Amino Acids”, Synthesis, 2022.
Sabadasch, V., Dachwitz, S., Hannappel, Y., Hellweg, T., Sewald, N.: Acrylamide-based Pd-Nanoparticle Carriers as Smart Catalyst for the Suzuki-Miyaura Cross-Coupling of Amino Acids. Synthesis. (2022).
Sabadasch, Viktor, Dachwitz, Steffen, Hannappel, Yvonne, Hellweg, Thomas, and Sewald, Norbert. “Acrylamide-based Pd-Nanoparticle Carriers as Smart Catalyst for the Suzuki-Miyaura Cross-Coupling of Amino Acids”. Synthesis (2022).
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