The role of palladium nanoparticles in catalytic C–C cross-coupling reactions

Trzeciak, Anna M.; Augustyniak, Adam W.

doi:10.1016/j.ccr.2019.01.008

Cited by 164 publications

(76 citation statements)

References 206 publications

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“…The key catalytic species in this reaction are Pd nanoparticles (NPs) which were generated in situ from the aggregates of amphiphilic NHC complexes during the reaction , . The fresh catalyst turned immediately into black when it was added into the mixture of p ‐nitrophenol and sodium borohydride indicating the formation of Pd NPs.…”

Section: Study Of Catalytic Activities Of 13–22mentioning

confidence: 99%

Amphiphilic Pd^II‐NHC Complexes on 1,3‐Alternate p‐tert‐Butylthiacalix[4]arene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions

et al. 2020

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Herein we report the first example of amphiphilic PdII–NHC complexes on the thiacalix[4]arene backbone in 1,3‐alternate configuration. Relative catalytic activity of synthesized PdII–NHC complexes in Suzuki–Miyaura coupling of haloarenes with phenylboronic acid was studied. A combination of micellar and metallocomplex catalysis was observed in Suzuki–Miyaura coupling upon going from pure DMF to water/DMF 3:1: the 2‐fold increase of conversion of 4‐bromoanisole unlike pure DMF was found. Interesting feature was found using chloroarene in DMF/water: the reaction selectivity changed from heterocoupling to homo coupling of phenylboronic acid. PdII–NHC complexes demonstrated a high activity in model hydrogenation reaction of p‐nitrophenol using sodium borohydride. The most lipophilic PdII–NHC complex was found to be most active, which can be attributed with additional p‐nitrophenol preconcentration in the aggregates due to larger hydrophobic capacity of macrocycle.

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Section: Study Of Catalytic Activities Of 13–22mentioning

confidence: 99%

Amphiphilic Pd^II‐NHC Complexes on 1,3‐Alternate p‐tert‐Butylthiacalix[4]arene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions

et al. 2020

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“…Since heterogeneous catalysis is based on processes taking place at the surface, the use of finely dispersed catalysts is often adopted in order to reduce the amount of material and maximize its catalytic effect [3,4]. For this purpose, palladium nanoparticles are widely used to catalyze organic reactions [5][6][7][8][9][10][11][12][13][14]. Similar to palladium, palladium(II) oxide (PdO) has also found applications in many catalytic processes [15][16][17][18], but few studies were carried out on the production of palladium oxide nanoparticles compared to the wide range of works concerning metallic palladium particles [19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

Palladium Oxide Nanoparticles: Preparation, Characterization and Catalytic Activity Evaluation

et al. 2020

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Stable palladium oxide nanoparticles were prepared in aqueous suspension with a very simple procedure, by dissolving palladium nitrate in water at a concentration around 10−4 M. UV-visible absorption spectroscopy was adopted to follow the formation of these nanoparticles, which were characterized by TEM microscopy, along with XRD, XPS and Raman measurements. DFT calculations allowed to interpret the Raman data and to clarify the species present at the surface of the nanoparticles. The catalytic activity of the latter was evaluated by monitoring the reduction of p-nitrophenol to p-aminophenol. This investigation paves the way to the use of these colloidal nanoparticles in processes of heterogeneous catalysis, in particular those concerning the catalytic degradation of aromatic derivatives that represent a serious danger for the environment as pollutants, as in the case of p-nitrophenol.

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“…[2] Furthermore, easily availables tarting materials and the efficient preparation of drugs, dyes, organic electronic and photonic materials, smart functional frameworks, and stimuliresponsive molecular architectures, in addition to many other well-established applications, are highlightso ft he recently emerging areas that utilize the Mizoroki-Heck reaction, where aryl halides 1 transform monosubstituted olefins 2 into disubstituteda lkenes 3 (Figure 1a). [3] Great practical potentialo fthe Mizoroki-Heck reactionw as confirmed by implementation of molecular, [4] nanoparticle, [5] anionic, [3d, 6] andh ybrid radical [7] catalytic systems.…”

Section: Introductionmentioning

confidence: 99%

Ionic Pd/NHC Catalytic System Enables Recoverable Homogeneous Catalysis: Mechanistic Study and Application in the Mizoroki–Heck Reaction

Eremin

Denisova

Kostyukovich

et al. 2019

Chemistry A European J

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In one word, how would you describe your research?Dynamic. How did this research begin?During our work on dynamic processes in Pd/NHC catalytic systems, one of the key techniques we utilized was mass spectrometry.E lectrospray ionization mass spectrometry was applied to understand possible reduction pathways of the studied Pd/NHC complexes. Surprisingly,s everal NHC-free species were detected, unstabilized palladium hydride being one of them. This elusive intermediate caught our attention and we delved into the study of the observed phenomena.What is the most significant result of this study?Formation of palladium complexes, non-stabilized by direct metal bonding with strong NHC ligand, makes av ery important point. Dynamic nature of the catalytic system allows ligand-free ionic palladium complexes to be formed. These ionic species do not agglomerate while being in Pd 0 oxidation state and, notably,t hey can be isolated from the reaction mixture and recycled. What was the inspiration for this cover design?Thinking about an artwork that might describe dynamic nature of the studied system, we wanted to highlight the ease with which the catalytic system can transform. This brought us to the sketch of palladium complexes on as eesaw.I nt he image we created, alternative palladium complexes play together as friends, seesawed easily up and down by the possibility of dynamic transformations.Invited for the cover of this issue are ValentineP .A nanikov and co-workers. The image depicts the dynamic behaviour of a Pd/NHCc atalytic systemw ith easy transition from molecular to ionic complex. Read the fullt ext of the article at

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The role of palladium nanoparticles in catalytic C–C cross-coupling reactions

Cited by 164 publications

References 206 publications

Amphiphilic Pd^II‐NHC Complexes on 1,3‐Alternate p‐tert‐Butylthiacalix[4]arene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions

Amphiphilic Pd^II‐NHC Complexes on 1,3‐Alternate p‐tert‐Butylthiacalix[4]arene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions

Palladium Oxide Nanoparticles: Preparation, Characterization and Catalytic Activity Evaluation

Ionic Pd/NHC Catalytic System Enables Recoverable Homogeneous Catalysis: Mechanistic Study and Application in the Mizoroki–Heck Reaction

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The role of palladium nanoparticles in catalytic C–C cross-coupling reactions

Cited by 164 publications

References 206 publications

Amphiphilic PdII‐NHC Complexes on 1,3‐Alternate p‐tert‐Butylthiacalix[4]arene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions

Amphiphilic PdII‐NHC Complexes on 1,3‐Alternate p‐tert‐Butylthiacalix[4]arene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions

Palladium Oxide Nanoparticles: Preparation, Characterization and Catalytic Activity Evaluation

Ionic Pd/NHC Catalytic System Enables Recoverable Homogeneous Catalysis: Mechanistic Study and Application in the Mizoroki–Heck Reaction

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Amphiphilic Pd^II‐NHC Complexes on 1,3‐Alternate p‐tert‐Butylthiacalix[4]arene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions

Amphiphilic Pd^II‐NHC Complexes on 1,3‐Alternate p‐tert‐Butylthiacalix[4]arene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions