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CC BY-NC-ND 4.0 · Synthesis 2022; 54(14): 3180-3192
DOI: 10.1055/a-1782-4224
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Acrylamide-Based Pd-Nanoparticle Carriers as Smart Catalysts for the Suzuki–Miyaura Cross-Coupling of Amino Acids

Viktor Sabadasch‡
a   Department of Chemistry, Physical and Biophysical Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany
,
Steffen Dachwitz‡
b   Department of Chemistry, Organic and Bioorganic Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany
,
Yvonne Hannappel
a   Department of Chemistry, Physical and Biophysical Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany
,
Thomas Hellweg∗
a   Department of Chemistry, Physical and Biophysical Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany
c   BINAS - Bielefeld Institute for Biophysics and Nanoscience, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany
,
Norbert Sewald  ∗
b   Department of Chemistry, Organic and Bioorganic Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany
› Author AffiliationsWe acknowledge financial support from Deutsche Forschungsgemeinschaft (SE 609/16-1).
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Abstract

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 N α-Boc-4-iodophenylalanine and N α-Boc-7-bromotryptophan with phenylboronic acid was carried out under ambient atmosphere in water at 20, 37, 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.

Key words

palladium catalysis - bioorganic chemistry - cross-coupling - amino acids - nanoparticles - polyacrylamide microgel - halogenated peptide - polymers

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1782-4224.
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Publication History

Received: 02 December 2021

Accepted after revision: 16 February 2022

Accepted Manuscript online:
25 February 2022

Article published online:
20 April 2022

© 2022. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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