Magnetic iron oxide nanoparticles–N‐heterocyclic carbene–palladium(II): a new, efficient and robust recyclable catalyst for Mizoroki–Heck and Suzuki–Miyaura coupling reactions

Abstract

A new and efficient nanoparticle–N‐heterocyclic carbene–palladium complex was synthesized and characterized using Fourier transform infrared spectroscopy, thermogravimetric analysis, field emission scanning electron microscopy, energy‐dispersive X‐ray analysis, X‐ray diffraction, transmission electron microscopy, elemental analysis, inductively coupled plasma analysis and vibrating sample magnetometry. This catalytic system was found to be a highly active catalyst in the Mizoroki–Heck and Suzuki–Miyaura cross‐coupling reactions. These reactions were best performed in dimethylformamide and water, respectively, in the presence of only 0.054 mol% of palladium under mild conditions. Moreover, the catalyst could be recovered easily and reused at least ten times without any considerable loss of its catalytic activity. Copyright © 2016 John Wiley & Sons, Ltd.

The Use of Palladium on Magnetic Support as Catalyst for Suzuki–Miyaura Cross-Coupling Reactions

“…Catalyst 15 performed very well when utilizing aryl bromides and aryl iodides, however, the yields dropped roughly 30% when the corresponding aryl chlorides were used (Table 2, Entry 20) [69]. A similar drop in yields was also experienced by Hajipour et al when they tested catalyst 16 with aryl chlorides (Table 2, Entry 21) [70]. However, with the more active aryl halides, viz.…”

Regioselective Heck reaction catalyzed by Pd nanoparticles immobilized on DNA-modified MWCNTs

“…14 Lauer and co-workers recently reported conditions for achieving excellent vinyl selectivity in the Heck coupling of cyclic olefins with aryl bromides using neopentyl phosphine ligands. In continuation of our recent investigations on the application of heterogeneous catalytic systems in cross-coupling reactions; [56][57][58][59][60] In this report, palladium is supported on the ss-DNA-functionalized MWCNTs materials to give a new and highly stable palladium catalyst (Pd/DNA@MWCNTs). Moreover, in concern to toxicity of palladium residuals, acceptable limits of palladium traces in pharmaceuticals were set usually as ppm level.…”

Cobalt supported on dendronized magnetic nanoparticles: A new highly efficient and recyclable catalyst for the Mizoroki–Heck cross‐coupling reaction

“…Several common solvents were tested for the Mizoroki-Heck cross-coupling reaction in the presence of MNP@PAMAM-Co to access the best optimal conditions ( Table 2, entries 13, [15][16][17][18][19][20]. This reaction proceeded in higher yields, more cleanly and faster when the reactions were conducted in a mixture of DMF and H 2 O in 1:1 ratio as solvent.…”

“…Therefore, improvement of efficacious methodologies for the formation of carbon-carbon bonds has been drawing considerable attention and become an active research field. For example, carbon nanotubes, despite having unique features, [7,12] are known to be hazardous to the environment. The standard Heck reaction is carried out using soluble palladiums, usually phosphine palladium complexes, but it suffers from disadvantages that limit its application in the industry.…”

“…[14] In this regard, application of biocompatible dendrimers as support is very promising due to their phenomenal and adjustable physicochemical features. [19] To date there are rare examples of the usage of metal-PAMAM anchored to MNPs with the catalytic demeanor in the organic transformations. [16,17] Attaching functional groups, such as hydroxyl, carboxyl and amine as terminal groups of the dendrimers can result in a considerable enhancement in binding capacity to a diversity of ions.…”