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Synfacts 2014; 10(1): 0101
DOI: 10.1055/s-0033-1340379
DOI: 10.1055/s-0033-1340379
Polymer-Supported Synthesis
Suzuki–Miyaura Coupling Using Polymer-Stabilized Pd Nanoparticles
Deraedt C, Salmon L, Ruiz J, Astruc D * Université de Bordeaux, Talence and Université de Toulouse, France
Efficient Click-Polymer-Stabilized Palladium Nanoparticle Catalysts for Suzuki–Miyaura Reactions of Bromoarenes and Reduction of 4-Nitrophenol in Aqueous Solvents.
Adv. Synth. Catal. 2013;
355: 2992-3001
Efficient Click-Polymer-Stabilized Palladium Nanoparticle Catalysts for Suzuki–Miyaura Reactions of Bromoarenes and Reduction of 4-Nitrophenol in Aqueous Solvents.
Adv. Synth. Catal. 2013;
355: 2992-3001
Further Information
Publication History
Publication Date:
13 December 2013 (online)
Key words
Suzuki–Miyaura coupling - palladium nanoparticles - aryl bromides - triazolyl-PEG polymers
Significance
Triazolyl-PEG polymer-stabilized palladium nanoparticles (PdNPs) 5 were prepared and applied to the Suzuki–Miyaura coupling. The reaction of aryl bromides 6 and phenylboronic acid (7) took place with 0.0001–0.01 mol% Pd of catalyst 5 to give the corresponding products 8 in 90–99% yield. The turnover number (TON) reached up to 990000.
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Comment
The Pd(II) catalyst 4 showed lower catalytic activity than the reduced catalyst 5 for the formation of 8f with 0.001 mol% Pd. For a quantitative reaction of 4-bromoacetophenone and phenylboronic acid, 22 hours were needed with catalyst 4 instead of two hours with PdNP catalyst 5. The average diameter of the Pd nanoparticles of 5 is 1.6 ± 0.3 nm.
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