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Issue 61, 2015
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Linkage of the PAMAM type dendrimer with the gel type resin based on glycidyl methacrylate terpolymer as a method of preparation of the polymer support for the recyclable palladium catalyst for Suzuki–Miyaura cross-coupling reactions

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Abstract

Poly(amidoamine) PAMAM type hyperbranched systems were immobilized on an epoxy functionalized polymer based on glycidyl methacrylate (the GMA resin). Two methods were applied. The first included two-stage synthesis of the zeroth order PAMAM dendrimer (1), starting from tris(2-aminoethyl)amine (TAEA), and its immobilization on the GMA resin. The second relied on multi-stage chemical modification of the GMA resin in turn with TAEA, methyl acrylate and ethylenediamine. The provided multi NH2-functionalyzed polymers (abbreviated respectively 2 and 5) were used for immobilization of palladium(II) ions to obtain two polymer supported palladium catalysts (2-Pd and 5-Pd, respectively). The synthesized polymers and polymer supported Pd catalysts were characterized using different instrumental techniques (FT-IR, DR UV-Vis, ICP-OES, DSC and SEM). Catalyst 2-Pd was found as a clearly more active in the model reaction of p-bromoanisole. It was tested successfully as catalysts in the Suzuki–Miyaura cross-coupling reactions of a series of aryl bromides with phenylboronic acid in water–organic solvent systems. It was also recycled successfully ten times in the coupling reaction of p-bromoanisole with phenylboronic acid carried out in the mixture of isopropyl alcohol and water (1 : 1 v/v) at 70 °C.

Graphical abstract: Linkage of the PAMAM type dendrimer with the gel type resin based on glycidyl methacrylate terpolymer as a method of preparation of the polymer support for the recyclable palladium catalyst for Suzuki–Miyaura cross-coupling reactions

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Supplementary files

Article information


Submitted
16 Mar 2015
Accepted
28 May 2015
First published
28 May 2015

RSC Adv., 2015,5, 49036-49044
Article type
Paper
Author version available

Linkage of the PAMAM type dendrimer with the gel type resin based on glycidyl methacrylate terpolymer as a method of preparation of the polymer support for the recyclable palladium catalyst for Suzuki–Miyaura cross-coupling reactions

A. Bukowska, W. Bukowski, K. Bester and S. Flaga, RSC Adv., 2015, 5, 49036
DOI: 10.1039/C5RA04637H

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