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Synthesis of gel-type imino-amino functionalized methacrylate-styrene terpolymers as supports for palladium catalysts for the Suzuki–Miyaura reaction

Paper ID Volume ID Publish Year Pages File Format Full-Text
40686 45862 2012 10 PDF Available
Title
Synthesis of gel-type imino-amino functionalized methacrylate-styrene terpolymers as supports for palladium catalysts for the Suzuki–Miyaura reaction
Abstract

Gel-type polymers uploaded with 8.5–15.4 wt% of palladium(II) ions based on the low cross-linked glycidyl methacrylate resins with imino-amino functionalities coupled with heterocyclic rings were prepared, characterized (FT-IR, DR UV–vis, HR-SEM, ICP-OES methods) and tested as catalysts in the Suzuki–Miyaura reactions of a series bromo- and chloroarenes with phenylboronic acid at 25–70 °C. The effects of the reaction medium, temperature, catalyst structure and concentration on the activity of the catalysts and Pd leaching were studied for the model reaction of bromobenzene with phenyl boronic acids. It was found that the catalysts with the branched system of TAEA were more active than those with the linear one (EDA). The activity of the catalysts strongly depended on the nature of heteroatoms of heterocyclic aldehyde moieties in imine ligands. The catalyst activity decreased in the order: 2-pyridinecarboxaldehyde (PA) > furfural (FA) > 2-thiophenecarboxaldehyde (TA). The best of the catalysts was used additionally in the reactions of substituted bromo- and chloroarenes. It turned out to catalyze efficiently the cross-coupling of bromoarenes bearing both electron donor and electron acceptor substituents. The reactivity of bromoarenes changed in the order: CHO > H∼F > Me > OMe ≫ OH. The catalyst was found inactive in coupling of 4-nitrochlorobenzene under the same reaction conditions. The catalyst with TAEA moieties was recycled in the reaction of bromobenzene minimum five times. Its activity, however, decreased gradually on each stage.

Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (192 K)Download as PowerPoint slideHighlights► Novel recyclable Pd catalysts for Suzuki–Miyaura reaction under mild conditions. ► Imino-amino functionalized methacrylate-styrene gels as supports for Pd catalysts. ► Pd(II) ion loading as a factor in determining the activity of polymer catalysts. ► An advantageous effect of branching ligand systems on the activity of Pd catalysts.

Keywords
Polymer supported palladium catalyst; Gel-type polymer supports; Imino-amino functionalized polymers; Suzuki–Miyaura reactions
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Synthesis of gel-type imino-amino functionalized methacrylate-styrene terpolymers as supports for palladium catalysts for the Suzuki–Miyaura reaction
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volumes 443–444, 7 November 2012, Pages 181–190
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us